CHAPTER THREE
The Literature of Heterocyclic Chemistry, Part XI, 2008–2009 L. I. Belen’kiia, Yu. B. Evdokimenkovab aN. D. Zelinsky
Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky Prospect, 119991 Moscow, Russia bLibrary of N. D. Zelinsky Institute of Organic Chemistry, Branch of Library of Natural Sciences, Russian Academy of Sciences, Moscow, Russia
Contents 1. Introduction 2. G eneral Sources and Topics 2.1. G eneral Books and Reviews 2.1.1. 2.1.2. 2.1.3. 2.1.4. 2.1.5.
T extbooks and Handbooks Annual Reports Nomenclature History of Heterocyclic Chemistry, Biographies Bibliography of Monographs and Reviews
2.2. G eneral Topics by Reaction Type 2.2.1. 2.2.2. 2.2.3. 2.2.4. 2.2.5.
eneral Sources and Topics G Structure and Stereochemistry Reactivity Synthesis Properties and Applications (Except Drugs and Pesticides)
2.3. S pecialized Heterocycles 2.3.1. N itrogen Heterocycles (Except Alkaloids) 2.3.2. Oxygen Heterocycles 2.3.3. Sulfur Heterocycles
2.4. N atural and Synthetic Biologically Active Heterocycles 2.4.1. 2.4.2. 2.4.3. 2.4.4. 2.4.5. 2.4.6. 2.4.7.
eneral Sources and Topics G Alkaloids Antibiotics Vitamins Drugs Pesticides Miscellaneous
3. T hree-Membered Rings 3.1. G eneral Topics 3.2. O ne Heteroatom 3.2.1. O ne Nitrogen Atom 3.2.2. One Oxygen Atom 3.2.3. One Sulfur Atom © 2013 Elsevier Inc. Advances in Heterocyclic Chemistry, Volume 108 ISSN 0065-2725, http://dx.doi.org/10.1016/B978-0-12-404598-9.00003-1 All rights reserved.
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3.3. T wo Heteroatoms 4. F our-Membered Rings 4.1. G eneral Topics 4.2. O ne Heteroatom 4.2.1. O ne Nitrogen Atom 4.2.2. One Oxygen Atom
4.3. T wo Heteroatoms 5. F ive-Membered Rings 5.1. G eneral Topics 5.2. O ne Heteroatom 5.2.1. 5.2.2. 5.2.3. 5.2.4.
eneral G One Nitrogen Atom One Oxygen Atom One Sulfur Atom
5.3. T wo Heteroatoms 5.3.1. 5.3.2. 5.3.3. 5.3.4. 5.3.5.
eneral G Two Nitrogen Atoms One Nitrogen and One Oxygen Atom One Nitrogen and One Sulfur Atom Two Sulfur Atoms
5.4. T hree Heteroatoms 5.4.1. T hree Nitrogen Atoms 5.4.2. Two Nitrogen Atoms and One Oxygen Atom 5.4.3. One Nitrogen Atom and Two Sulfur Atoms
5.5. F our Heteroatoms 6. S ix-Membered Rings 6.1. G eneral 6.2. O ne Heteroatom 6.2.1. O ne Nitrogen Atom 6.2.2. One Oxygen Atom
6.3. T wo Heteroatoms 6.3.1. T wo Nitrogen Atoms 6.3.2. One Nitrogen and One Oxygen Atom 6.3.3. One Nitrogen and One Sulfur Atom
6.4. T hree Heteroatoms 6.4.1. Three Nitrogen Atoms
6.5. F our Heteroatoms 7. R ings with More than Six Members 7.1. G eneral 7.2. S even-Membered Rings 7.2.1. O ne Heteroatom 7.2.2. Two Heteroatoms 7.2.3. Three and More Heteroatoms
7.3. M edium Rings
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7.4. L arge Rings 7.4.1. G eneral Problems 7.4.2. Crown Ethers and Related Compounds 7.4.3. Miscellaneous Macroheterocycles
8. H eterocycles Containing Unusual Heteroatoms 8.1. P hosphorus Heterocycles 8.1.1. C hemistry of Individual Classes of P-Heterocycles 8.1.2. Structure and Stereochemistry 8.1.3. Synthesis
8.2. B oron Heterocycles 8.2.1. C hemistry of Individual Classes of B-Heterocycles 8.2.2. Synthesis 8.2.3. Applications
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8.3. S ilicon, Germanium, Tin, and Lead heterocycles
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8.3.1. C hemistry of Individual Classes of Heterocycles 8.3.2. Synthesis
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8.4. S elenium and Tellurium Heterocycles 8.4.1. G eneral Sources and Topics 8.4.2. Chemistry of Individual Classes of Heterocycles
8.5. O ther Unusual Heterocycles 8.5.1. M etallacycles 8.5.2. Metal Chelates and Related Complexes
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Abstract The survey is a sequel to 10 already published in Advances in Heterocyclic Chemistry. It includes monographs and reviews published during the period 2008–2009 as well as some published earlier but omitted in Part X. Just as in Parts III–X, sources not only in English but also in Russian, Japanese, Chinese, and other languages are surveyed and classified. This feature of the survey should cause no problem because some of the sources are available in English translations and practically all others have informative English abstracts as well as quite understandable and useful schemes and lists of references. As before, carbohydrates are not covered. Such compounds are mentioned only in general cases (e.g. anomeric effect) as well as when carbohydrates serve as starting compounds for the synthesis of other heterocycles or they are present as fragments of a complex system including another heterocyclic moiety such as nucleosides.
KEYWORDS General sources and topics; Natural and synthetic biologically active heterocycles; Three-membered rings; Four-membered rings; Five-membered rings; Six-membered rings; Rings with more than six members; Heterocycles with unusual heteroatoms
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1. INTRODUCTION This survey is a sequel to 10 already published in Advances in Heterocyclic Chemistry [66AHC(7)225; 79AHC(25)303; 88AHC(44)269; 92AHC(55)31; 98AHC(71)291; 99AHC(73)295, 01AHC(79)199, 04AHC(87)1, 06AHC (92)145, 11AHC(102)1]. It includes monographs and reviews published during the period 2008–2009 as well as some published earlier but omitted in Part X. Just as in Parts III–X, sources not only in English but also in Russian, Japanese, Chinese, Czech, and other languages are surveyed and classified. This feature of the survey should cause no problem because some of the sources are available in English translations and practically all others have informative English abstracts as well as quite understandable and useful schemes and lists of references. As before, carbohydrates are not covered. Such compounds are mentioned only in general cases (e.g. anomeric effect) as well as when carbohydrates serve as starting compounds for the synthesis of other heterocycles or they are present as fragments of a complex system including another heterocyclic moiety such as nucleosides.
2. GENERAL SOURCES AND TOPICS 2.1. General Books and Reviews 2.1.1. Textbooks and Handbooks Fundamentals of organic chemistry of cosmetic remedies: 08MI1. 2.1.2. Annual Reports
2.1.2.1. C omprehensive reports summarized specialized reports devoted to basic series of heterocycles (2006 and 2007) were cited in 11AHC(102)1 from 08MI2 and 09MI1 2.1.2.2. Reports devoted to individual problems
Heterocyclic chemistry, 08AR(B)106; 09AR(B)129. Synthetic methods Part (I). Free-radical reactions: 08AR(B)19; 09AR(B)19. Synthetic methods Part (II). Oxidation and reduction methods: 08AR(B)35; 09AR(B)35. Synthetic methods in heteroatom chemistry (P-, S-, Se-, Te-, and Si-heterocycles): 08AR(B)49. Organocatalysis (heterocycles as catalysts and reactions with participation of heterocycles): 08AR(B)88; 09AR(B)113.
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Marine natural products: 08AR(B)127; 09AR(B)150. Synthesis highlights (total syntheses of some natural products exhibiting antitumor, antiparasitic, neuropharmacological, and anti-HIV activity): 08AR(B)142; 09AR(B)167. Supramolecular chemistry (molecular recognition, structure and assembly, and functional systems): 08AR(B)164; 09AR(B)190. Biotransformations: 09AR(B)206. N-Heterocyclic carbene-containing complexes in catalysis: 08AR(B)184; 09AR(B)232. Reaction mechanisms. Pericyclic reactions: 08AR(B)260; 09AR(B)285. Enantioselective catalysis, reaction mechanisms: 09AR(B)421. Organic photochemistry (complex photoluminescence, DNA sequencedirected structure and dynamics studies, photopolymerization, and photocatalysis as important topics): 08AR(B)349; 09AR(B)380. Organometallics: transition metals in organic synthesis: 09AR(B)93. Advances in the syntheses of quinoline and quinoline-annulated ring systems since 2005: 08COC1116. Anion receptors based on organic frameworks: highlights from 2005 and 2006: 08CSR151. Recent applications of oxazoline-containing ligands in asymmetric catalysis (2004–2007): 09CRV2505. Recent developments (from 2003 to 2007) in dynamic kinetic resolution: 08T1563. Recent developments in enantioselective gold(I) catalysis (intramolecular hydrofunctionalization of allenes with carbon and heteroatom nucleophiles to form carbocyclic and heterocyclic compounds with up to 99% e.e. since 2005): 08CEJ5382. Recent developments in microwave-assisted, transition metal-catalyzed C–C and C–N bond-forming reactions, particularly, used in the synthesis of heterocycles and published from the end 2004 until the first part of 2007: 08EJO1133. Synthetic applications of carbolithiation transformations (review of the data published since 2000, particularly, on examples of various heterocycles): 08CC3839. Transition metals in organic synthesis: Highlights for the year 2005: 08CCR57. 2.1.3. Nomenclature Guide to draw up names of heterocyclic compounds with examples and problems: 09MI2. Nomenclature of natural products: 08MI3.
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2.1.4. History of Heterocyclic Chemistry, Biographies Chemistry of heterocyclic compounds in A. E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch of Russian Academy of Sciences for 50 years: 08KGS1443. Chemistry of heterocyclic compounds in Institute of Organic Chemistry, National Academy of Sciences, Ukraine: 09KGS485. Overview of 40 years’ chemical study (scientific biography of Dr T. Imanishi): 09YZ107. Search of novel bioactive natural products from plant sources: 09YZ1155. 2.1.5. Bibliography of Monographs and Reviews Specialized surveys: 09KGS466; 09KGS939; 09KGS1107; 10KGS(11)I; 11KGS(1)I.
2.2. General Topics by Reaction Type We have classified many reviews dealing with these materials under the following headings: 1. G eneral Sources and Topics. 2. S tructure and Stereochemistry (it is self-subdivided into Theoretical Aspects, Stereochemical Aspects, Betaines and Other Usual Structures, Miscellaneous Substituted Heterocycles). 3. R eactivity (General Topics: Reactions with Electrophiles and Oxidants, Reactions with Nucleophiles and Reducing Agents, Reactions toward Free Radicals, Carbenes etc., Heterocycles as Intermediates in Organic Synthesis). 4. S yntheses (General Topics and Nonconventional Synthetic Methodologies, Synthetic Strategies and Individual Methods,Versatile Synthons and Specific Reagents, Ring Synthesis from Nonheterocyclic Compounds, Syntheses by Transformation of Heterocycles). 5. P roperties and Applications (Dyes and Intermediates, Substances with Luminescent and Related Properties, Organic Conductors, Coordination Compounds, Polymers, Ionic Liquids, Miscellaneous). 2.2.1. General Sources and Topics Heterocycles in the service of humankind: 09ARK(9)248. Microwave-assisted organic synthesis, particularly, that of heterocycles and transformations, particularly, in ionic solvents: 08ACR629. Spiroconjugation effect and application: 09CJO517.
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2.2.2. Structure and Stereochemistry 2.2.2.1. Theoretical aspects
Binding mechanisms in supramolecular complexes: 09AG(E)3924. Boron atoms as spin carriers in two- and three-dimensional systems: 09AG(E)5082. The ins and outs of proton complexation (mainly, with heterocycles): 09CSR1663. Computed crystal energy landscapes for understanding and predicting organic crystal structures and polymorphism, including heterocycles: 09ACR117. New properties and reactions within discrete, self-assembled hosts: 09AG(E)3418. Peripheral covalent modification of inorganic and organometallic compounds through C–C bond formation reactions: 08CRV4185. Pulse electron–electron double resonance–ESR spectroscopy in nanometer range, particularly, its use in structural studies of nitroxyl biradicals: 08UK515. Structure and characteristics of ionic forms of heteroarenium salts in organic solvents: 09KGS1603. Supramolecular coordination chemistry (heterocycles as ligands): 08AG(E)8794. 2.2.2.2. Molecular dimensions
Engineering discrete stacks of aromatic (and heteroaromatic) molecules: 09CSR1714. Foldamers (mainly, synthetic heterocycle-based receptors) with helical cavities for binding complementary guests: 09CSR3316. Guanosine hydrogen-bonded scaffolds: A new way to control the bottom-up realization of well-defined nanoarchitectures: 09CEJ7792. Recent advances in the development of aryl(or hetaryl)-based foldamers: 09CSR1726. 2.2.2.3. Stereochemical aspects
Asymmetric catalysis with bifunctional cinchona alkaloid-based urea and thiourea organocatalysts: 08CC2499. Asymmetric and fused heterocycles based on [2.2]paracyclophane: 09T8055. Binaphthol-derived phosphoric acid as a versatile catalyst for enantioselective carbon–carbon bond forming reactions, in particular, Friedel–Crafts reactions of heterocycles: 08CC4097.
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Bite angle effects of diphosphines in C–C and C–X bond forming crosscoupling reactions, particularly, with participation of heterocycles: 09CSR1099. Chiral guanidine-catalyzed enantioselective reactions: 09CAJ488. Cinchona-based phase transfer catalysts for asymmetric synthesis: 09CC7090. Conformationally complex π-conjugated molecular and polymeric materials: 09CEJ5176. Cooperative Lewis acid/base systems combining achiral Lewis acids with chiral cinchona alkaloid nucleophiles, to catalyze highly enantioselective cycloaddition reactions between ketene enolates and various electrophiles: 08ACR655. Design, synthesis and evaluation of (+)-sparteine surrogates for asymmetric synthesis: 08CC655. Helical chiral pyridine N-oxides: A new family of asymmetric catalysts: 09CEJ7268. Iridium catalysts for asymmetric hydrogenation, particularly, that of heteroaromatic substrates (quinolines, pyridines, furans): 08CCR513. Mechanistic manifold and new developments of the Julia–Kocienski reaction, particularly, stereochemical trends for heteroaryl sulfones: 09EJO1831. Organocatalytic asymmetric oxidation: 08CJO588. Organocatalytic asymmetric Friedel–Crafts reactions (N-heterocycles as substrates and catalysts): 08CJO605. Organocatalyzed asymmetric Mannich reactions (proline and its derivatives as catalysts): 08CSR29. Supramolecular chemistry at interfaces: Molecular recognition on nanopatterned porous surfaces: 09CEJ7004. Synthesis of unusually strained spiroheterocyclic ring systems (oxaspiro[2.2] pentanes, 1,4-dioxaspiro[2.2]pentanes, 1-oxaspiro[2.3]hexanes, 4-oxaspiro[2.3] hexanes, 1,4-dioxaspiro[2.3]hexanes) and their exploits in synthesis: 09T5879. Three-fold symmetry in asymmetric catalysis using tris(oxazolinyl)ethanes (Trisox): 08CEJ4142. Vibrational circular dichroism, a new tool for the determination of absolute configuration of chiral molecules, mainly natural products: 09CJO848. 2.2.2.4. Betaines and other unusual structures
Construction of supramolecular systems based on endohedral metallofullerenes (particularly, complexes with crown compounds and organic donors): 09BCJ171.
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Coordination structures of metalloporphyrins with N-containing cations in complexes with fullerenes: 09MG190. Development of catalytic carbene transfer reactions using alkynes as a source of carbenes, particularly, 2-furyl-, 2-pyrroryl-, and 2-thienylcarbene complexes: 09YGK1161. Heteropentalene mesomeric betaines of type C: 08H1. Supramolecular donor–acceptor hybrids of porphyrins/phthalocyanines with fullerenes/carbon nanotubes: electron transfer, sensing, switching, and catalytic applications: 09CC4913. 2.2.2.5. Miscellaneous-substituted heterocycles
Azulenes fused to heterocycles: 09AHC(97)131. Chemistry of cross-conjugated dienones including 3,5-bis-hetarylmethylidene ketones: 08UK707. Enamides as valuable organic substrates, particularly, in reactions with heterocycles and in syntheses of the latter: 08OBC3455. Peri-annulated heterocyclic systems1: 08AHC(95)1. 2.2.3. Reactivity
2.2.3.1. General topics
Anionic reduced forms of electron-deficient N-hetarenes in reactions with C-electrophiles to form C–C bond: 08UK639. Desymmetrization of meso-bicyclic hydrazines: An efficient strategy toward the synthesis of functionalized cyclopentenes: 09SL2885. Direct conversion of carbon–hydrogen into carbon–carbon bonds by first-row transition metal catalysis, particularly, Cu- and Ni-based arylation reactions of heteroaromatics: 09S4087. Heterocycles as key substrates in multicomponent reactions: 08CEJ8444. Intermolecular addition reactions of acyclic and cyclic, particularly, pyrrolidinone-based N-acyliminium ions: 09S339; 09S513. Iron-catalyzed carbon–heteroatom and heteroatom–heteroatom bond forming processes: 08CSR1108. Palladium-catalyzed alkynylation of aryl and hetaryl halides: 09SL2896. Reactions in the conjugated “ene-ene-yne” manifold: five-membered heteroaromatic ring fragmentation and ring formation via coarctate/pseudocoarctate mechanisms: 08CSR343. Sigmatropic rearrangements of “onium” ylids including heterocyclic ones: 09CSR1027.
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Stereoselective transformations of meso-bicyclic hydrazines as versatile access to functionalized aminocyclopentanes: 09S869. Structure and reactivity of nitrenium ions including heterocyclic, electrophilic amination of heterocycles, thermolysis of aminopyridinium salts: 08UK419. Transition-metal-catalyzed site-selective cross-coupling of di- and polyhalogenated compounds, in particular, hetarenes: 09S1405. 2.2.3.2. Reactions with electrophiles and oxidants
Electrophilic iodination of organic compounds (particularly, heterocycles) using elemental iodine or iodides: 08S1487. Metal ion-coupled and proton-coupled electron-transfer reduction of dioxygen for one-electron reductants such as ferrocene derivatives, twoelectron reductants such as NADH analogs, and four-electron reduction with cofacial dicobalt porphyrins: 08CL808. Oxydation of heterocyclic compounds with manganese dioxide: 09KGS803. Recent progress in the immobilization of catalysts for selective oxidation in the liquid phase, particularly, based on supported ionic liquid phases: 08CC1727. 2.2.3.3. Reactions with nucleophiles and reducing agents
Amination of aryl and hetaryl chlorides catalyzed by palladium complexes: 08UK177. Samarium iodides: Catalysts for the formation of carbon–nitrogen bonds (in particular, ring opening of epoxides with nitrogen nucleophiles and transformation of N-acyloxazolidinones into esters): 09SL2051. Transition metals in amination of chloroarenes and chlorohetarenes: 09UK1113. 2.2.3.4. Reactions toward free radicals, carbenes, etc.
Application of N-heterocyclic carbenes as organocatalysts: 08YGK377. Chiral, chelating, hydroxyalkyl and hydroxyaryl N-heterocyclic carbenes: Design, synthesis, and application in copper-catalyzed asymmetric conjugate addition (Cu–ACA): 09AA43. High oxidation state transition metal complexes ligated with N-heterocyclic carbenes: 08COC1468. Development of C–C bond formation and asymmetric reactions catalyzed by N-heterocyclic carbenes: 08YZ1179.
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Discovering new reactions with N-heterocyclic carbene catalysis: 09AA55. Fischer-type group 6 carbene complexes in the synthesis of optically active molecules: 09COC31. N-Heterocyclic carbene–copper complexes: Synthesis and applications in catalysis: 08AA43. N-Heterocyclic carbenes in gold catalysis: 08CSR1776. Metal-assisted and metal-templated reactions of Fischer carbene complexes in organic synthesis: 09CRV3227. Nonmetathetic utility of Grubbs’ ruthenium carbenes, particularly, in reactions with participation or formation of heterocycles: 09CRV3817. Progress in preparation of chiral metal complexes of N-heterocyclic carbenes and their use as catalysts in asymmetric reactions: 09CJO1499. Recent advances in carbon–carbon bond-forming reactions involving homoenolates generated by nucleophilic heterocyclic carbene catalysis: 08CSR2691. Recent progress in application of N-heterocyclic carbene metal complexes to ketone hydrosilylation: 09CJO1938. Surveying sterically demanding N-heterocyclic carbene ligands with restricted flexibility for palladium-catalyzed cross-coupling reactions: 08ACR1523. Synthesis and coordination chemistry of heterocyclic carbenes: 08AG(E)3122. Synthesis, properties, and organometallic chemistry of carbenes including N-heterocyclic carbenes: 09CCR862. Well-defined N-heterocyclic carbenes–palladium(II) precatalysts for cross-coupling reactions: 08ACR1440. 2.2.3.5. Heterocycles as intermediates in organic synthesis
Advanced approach to polycyclics (including heterocyclic frameworks) by a synergistic combination of enyne metathesis and Diels–Alder reaction: 09CSR2065. Advances in exploring heterocyclic dienoxysilane nucleophiles in asymmetric synthesis: 09SL1525. Catalytic asymmetric direct Mannich reaction (heterocycles as catalysts) in the synthesis of α,β-diamino acids: 09CSR1940. Coupling reagents, including N-, O-, and S-heterocycles, for amide bond formation: 09CSR606. Functional group-directed ortho-arylation of aromatic rings catalyzed by transition metal complexes of 2-arylpyridines: 09YGK229.
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Latent olefin metathesis catalysts with heterocyclic ligands: 09CSR3360. Organocatalysis—after the gold rush: 09CSR2178. Organocatalytic asymmetric aza-Michael additions (particularly, N-heterocycles as nucleophiles and/or products): 09CEJ11058. Transition metal-catalyzed hydroarylation (as well as hydrohetarylation) reactions of alkynes through direct functionalization of C–H bonds: A convenient tool for organic synthesis: 09EJO1111. 2.2.4. Synthesis
2.2.4.1. General topics, nonconventional synthetic methodologies
Advances and applications of Mitsunobu and related reactions: 09CRV2551. Application of β-alkoxyvinyl trifluoromethyl ketones to the synthesis of heterocycles: 08CJO2023. Application of stable nitrenium ions to preparative organic chemistry: 09H(78)571. Applications of biotransformations and biocatalysis to complexity generation in organic synthesis: 09CSR3117. Applications of multicomponent reactions to the synthesis of diverse heterocyclic scaffolds: 09CEJ1300. Aromatic compounds as synthons for 1,3-dicarbonyl derivatives useful, particularly, in the synthesis of heterocycles: 09CSR3082. Backbone amide linker in solid-phase synthesis (particularly, heterocycles as linkers): 09CRV2092. C–F Bond activation (particularly, in heteroaromatic fluorides) in organic synthesis: 09CRV2119. Carbonyl and olefin adducts of coinage metals supported by poly(pyrazolyl)borate and poly(pyrazolyl)alkane ligands and silver-mediated atom transfer reactions: 08CRV3223. Chiral tertiary diamines (proline, aziridine, diazadecaline derivatives as ligands) in asymmetric synthesis: 08CRV140. Coinage metal-assisted synthesis of heterocycles: 08CRV3395. Cross-dehydrogenative coupling (C–C bond formations beyond functional group transformations): 09ACR335. “Designer reagents” recombinant microorganisms: new and powerful tools for organic synthesis: 09T947. Direct functionalization of nitrogen heterocycles via Rh-catalyzed C–H bond activation: 08ACR1013. Direct phosphonylation of aromatic azaheterocycles: 09CRV2672.
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Efficient synthesis of methylenetetrahydrofurans and methylenepyrrolidines by formal [3 + 2] cycloadditions of propargyl substrates: 08CEJ6026. Enamines as precursors to polyfunctional heteroaromatic compounds; 08H(75)1849. Enantioselective catalysis and complexity generation from allenoates (particularly, syntheses of heterocycles): 09CSR3102. Equilibrium ring-closing metathesis: 09CRV3783. Fluorous linker-facilitated chemical synthesis: 09CRV749. Heterocyclization of thioamides containing active methylene group: 08KGS1763. Hypervalent iodine(III) reagents in organic synthesis: 09ARK(1)1. Ionic liquids in heterocyclic synthesis: 08CRV2015. Lewis base catalysis in organic synthesis: 08AG(E)1560. Mechanism of annulations ([2 + 4] cyclocondensations) of Schiff bases by β-di- and β,β′-tricarbonyl compounds in amphyprotonic media: 08KGS335. Metal-catalyzed one-step synthesis as direct alternatives to multistep heterocycle and amino acid derivative formation: 09CEJ302. Metal vinylidenes as catalytic species in organic reactions leading to heterocycles: 08CAJ164. Metathesis in the synthesis of aromatic and heteroaromatic compounds: 09CRV3743. Microwave dielectric heating in synthetic organic chemistry: 08CSR1127. Microwave-enhanced synthesis: 09T3325. Palladium- and copper-catalyzed arylation of carbon–hydrogen bonds: 09ACR1074. Phosphonium coupling in the direct bond formations of tautomerizable heterocycles via C–OH bond activation: 09EJO461. Photochemical reactions as key steps in organic synthesis: 08CRV1052. Progress in the copper(I)-catalyzed multicomponent reactions: 09CJO174. Radicals in organic synthesis: 09T8603. Ring-closing metathesis as a novel route to aromatic heterocycles: 08CEJ5716. Silicon- and germanium-substituted propynals as ambident electrophiles for design of new heterocycles and polyfunctional acetylenes: 08IZV914. Silver-mediated coupling and heterocyclization reactions: 08CRV3149. Silver-mediated synthesis of heterocycles: 08CRV3174.
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Solvent-free heterocyclic synthesis: 09CRV4140. Superelectrophiles in heterocyclic ring-forming reactions: 09ARK(1)63. Synthesis of 2H-chromenes and 4H-chromenes, diastereoselective synthesis of substituted aziridines and oxiranes, particularly, cyclohexadiene epoxides, diastereo- and enantioselective synthesis of dihydrofuran derivatives, enantioselective synthesis of isoxazoline N-oxide: 08ACR937. Synthesis of heterocyclic compounds using oxaloacetic ester (diethyl 2-oxosuccinate): 08KGS163. The tandem Claisen rearrangement in the construction of building blocks for supramolecular chemistry: 08CSR2413. Transformation of phenolic hydroxyl into acyl group, particularly, in heterocycles as a new tool in organic synthesis: 09ARK(1)81. Transition metal-catalyzed direct arylation of (hetero)arenes by C–H bond cleavage: 09AG(E)9792. α-Trifluoromethylated carbanion synthons, particularly, in syntheses and reactions of heterocycles: 08ACR817. Ultrasound in heterocyclic chemistry: 09T2619. Ylide-initiated Michael addition–cyclization reactions in synthesis of N-, O-, and N,O-heterocycles: 2.2.4.2. Synthetic strategies and individual methods
Advances in the Baylis–Hillman reaction-assisted synthesis of carbo- and heterocyclic frameworks: 08T4511. Alkoxyallenes as powerful C3 building blocks toward highly functionalized heterocycles: 09ACR45. Aminophosphine catalysts in modern asymmetric synthesis. Cyclic aminophosphines and aminophosphites as catalysts: 08AA15. Asymmetric aminocatalysis—Gold rush in organic chemistry (proline, imidazolidinones and other N-heterocycles as catalysts): 08AG(E)6138. Asymmetric Baylis–Hillman reaction: 08SL2897. Asymmetric cascade reactions catalyzed by chiral secondary amines: 08OBC2037. Asymmetric organocatalysis (particularly, cyclic amines as catalysts and synthesis of natural products): 08AG(E)4638. Biaryl phosphane ligands in palladium-catalyzed amination (C–N crosscoupling reactions in the synthesis of heterocycles and pharmaceuticals, in materials science, and in natural product synthesis): 08AG(E)6338. Brønsted acid catalysis of asymmetric Friedel–Crafts and aza-Diels–Alder reactions: 08AA31.
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Catalytic asymmetric intramolecular Stetter reaction leading to heterocycles: 09SL1189. Catalytic C–C, C–N, and C–O Ullmann-type coupling reactions: 09AG(E)6954. Combinatorial transition-metal catalysis: Mixing monodentate P ligands to control enantio-, diastereo-, and regioselectivity: 08AG(E)2556. Consecutive multicomponent syntheses of heterocycles via palladiumand copper-catalyzed generation of alkynones: 08ARK(1)195. Construction of heterocycles by the use of alkyne π-activation in catalyzed cascade reactions: 08S3183. Construction of heterocycle scaffolds via transition metal-catalyzed sp2 C–H functionalization: 09ASC2243. Copper/amino acid-catalyzed cross-couplings of aryl and vinyl halides with amines or N-heterocycles as nucleophiles: 08ACR1450. Development of novel methods for synthesis of heterocyclic compounds catalyzed by transition metals in fluorinated alcohols: 08YZ1133. Functionality of amidines and amidrazones (particularly, their applications in synthesis of heterocycles): 08ARK(1)153. Group 9 metal complex-catalyzed hydrogen transfer reactions and their application to organic synthesis, particularly, to hydrogenation of nitrogen heteroaromatics and formation of N-heterocycles: 08YGK322. The growing synthetic utility of the Weinreb amide, particularly, in heterocyclic chemistry: 08S3707. Michael additions to activated vinylphosphonates in the synthesis of carbocyclic and heterocyclic compounds: 09S1227. New development of oxa-Michael reaction: 09CJO1544. One-pot cyclizations of (2,4-dioxobutylidene)phosphoranes and (2-alkoxy-4-oxobut-2-enylidene)phosphoranes to form carbocyclic and heterocyclic ring systems: 08S3877. Osmium and palladium in alkene activation and oxidation: 08S1325. Palladium(II)-catalyzed C–H activation/C–C cross-coupling reactions: 09AG(E)5094. Practical organocatalysis with (S)- and (R)-5-pyrrolidin-2-yl-1H-tetrazoles: 08AA3. The Pschorr reaction, a fresh look at a classical transformation leading to polycyclic carbo- and heterocycles: 09COS193. Recent progress in three-component reactions leading to heterocycles: 09OPP1. Recent progress in the use of fluoroorganic compounds in pericyclic reactions: 09T9905.
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Stereoselective synthesis of saturated heterocycles via palladium-catalyzed alkene carboetherification and carboamination reactions: 08SL2913. Strategies for innovation in multicomponent reaction design: 09ACR463. Synthesis of carbo- and heterocycles via multicomponent reactions of carbonyl compounds and derivatives of cyanoacetic acid: 08S1. Synthesis of six-membered oxygenated heterocycles through carbon– oxygen bond-forming reactions: 08T2683. Transition metal-catalyzed C–C bond formation via C–H bond cleavage: 08S3013. Utilization of N–X bonds in the synthesis of N-heterocycles: 09ACR1172. 2.2.4.3. Versatile synthons and specific reagents
Alkyne activation with Brønsted acids, iodine, or gold complexes, and its fate leading to synthetic application (particularly, to five- and six-membered heterocycles): 09CC5075. Allenes as dipolarophiles and 1,3-dipole precursors: Synthesis of carbocyclic and heterocyclic compounds: 09COC1406. Application of sulfamic acid in organic synthesis, particularly, in the synthesis of heterocycles: 09COC1002. Applications of zirconium(IV) compounds in organic synthesis, particularly, in the synthesis of heterocycles: 09COC1. Applications of zirconium(IV) chloride in organic synthesis: 08S829. Aryl and heteroaryl trifluoroborates and monocoordinated palladium complexes as catalysts—a perfect combination for Suzuki–Miyaura coupling: 09AG(E)9240. Benzoylpyruvates in heterocyclic chemistry: 09JHC1. Catalytic C–H amination, particularly, selective intramolecular nitrene C–H insertion leading to N-heterocycles: 09CC5061. Catalytic Kabachnik–Fields reaction (particularly, phthalocyanine catalysts and heterocyclic components in the reaction): 08ARK(1)1. Concerted nucleophilic substitution reactions at vinylic carbons, particularly, reactions with O-, S-, and N-nucleophiles leading to heterocycles: 09SL2549. Construction of nitrogen-containing heterocycles by C–H bond functionalization: 09CEJ5874. Copper-catalyzed multicomponent reactions: Securing a catalytic route from the cycloaddition of 1-alkynes and sulfonyl- or phosphoryl azides followed by ring-opening rearrangement of the initially formed copper
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triazole species to give ketenimine intermediates and reactivities of the latter: 09COC1766. Design of novel, synthetically useful (thio)urea-based organocatalysts including their use in syntheses and reactions of heterocycles: 09SL354. Dimedone:A versatile precursor for annulated heterocycles:09AHC(98)1. Dimethylformamide dimethyl acetal as a building block in heterocyclic synthesis: 09JHC801. From azides to nitrogen-centered radicals: Applications of azide radical chemistry to organic synthesis, particularly, of N-heterocycles: 09CEJ7830. Green synthesis of ferrocenyl-substituted heterocycles: 08CJO791. Halovinyl aldehydes: useful tools in organic synthesis including O- and N-heterocycles: 08T2883. Heterocycles from trifluoromethanesulfonamide: Formation and structure: 09MRO66. Hydrazinecarbothioamide group in the synthesis of heterocycles: 09ARK(1)150. Multicomponent heterocycle syntheses via catalytic generation of alkynones: 09COC1777. Organocatalytic domino reactions (heterocycles as catalysts and/or reactants and products): 09COC1432. Oxidative alkylamination of aromatic and heteroaromatic substrates and accompanying heterocyclizations thereof: 08IZV899. The Pd/Cu-catalyzed desulfitative C–C cross-coupling of heteroaromatic thioethers with organostannanes or boronic acids (Liebeskind–Srogl reaction): 09AG(E)2276. Phosphine-triggered synthesis of functionalized cyclic compounds, particularly, heterocycles: 08CSR1140. Polynitromethanes—Unique reagents in the synthesis of nitro-substituted heterocycles: 09SL1543. Progress in the synthesis of trifluoromethylated heterocyclic compounds based on ethyl 4,4,4- trifluoroacetoacetate and its derivatives: 09COC1015. Progress in synthetic application of iodine as a Lewis acid catalyst: 09CJO1719. Properties, preparation and synthetic uses of amine N-oxides including heteroaromatic and cyclic enamine N-oxides: 09OPP173. Reactions of hydrazonoyl halides with heterocyclic thiones. Convenient methodology for heteroannulation, synthesis of spiroheterocycles and heterocyclic ring transformation: 08ARK(1)18.
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Recent advances in the application of bromodimethylsulfonium bromide (BDMS) as versatile reagent in organic synthesis: 09T9513. Recent applications of heteropoly acids and related compounds in synthesis of heterocycles: 09MRO359. Recent developments in the use of bis-(trichloromethyl) carbonate in synthesis, particularly, of heterocycles: 09OPP93. Recent extensions of the Morita–Baylis–Hillman reaction, particularly, those leading to heterocycles: 09CC5496. Ru(II) catalysts supported by hydridotris(pyrazolyl)borate for the hydroarylation of olefins: 09ACR585. Selective reactions on the azido groups of aromatic polyazides, particularly, 1,3-dipolar cycloaddition reactions: 09SL1. Sulfur monochloride in the synthesis of heterocyclic compounds: 08AHC(96)175. Synthesis of aminoboronic acids and their applications in bifunctional catalysis: 09ACR756. Synthetic applications of benzenediol:oxygen oxidoreductase (laccase) in green chemistry: 09ASC1187. Synthesis of fluorinated arenes and hetarenes based on one-pot cyclizations of 1,3-bis(trimethylsilyloxy)-1,3-butadienes: 09SL2205. Synthesis of heterocycles using trimethylsilyldiazomethane: 09YGK357. Synthetic use of molecular iodine, particularly, in preparation of heterocycles: 08YGK652. The use of 2-arylhydrazonals in the synthesis of five- and six-membered heterocycles: 09SL3237. Vinyl-, propargyl-, and allenylsilicon reagents in asymmetric “green” synthesis of carbo- and heterocycles: 09CEJ5402. 2.2.4.4. Ring synthesis from nonheterocyclic compounds
Asymmetric hetero-Diels–Alder reactions of carbonyl compounds: 09T2839. Chemistry of deprotonated α-aminonitriles including their participation in syntheses and transformations of heterocycles: 09S1941. Development of facile syntheses of heterocycles using heteroatom– halogen bonds: 09YGK1001. Electrophilic addition and cyclization reactions of allenes to give, particularly, thiiranes and lactones: 09ACR1679. Enantioselective radical cyclization for the synthesis of cyclic compounds: 09H(79)229.
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Formation of five- and six-membered heterocyclic rings by radical cyclization: 09COC599. Intramolecular haloetherification and transannular hydroxycyclization of alkenes. A synthetic methodology to obtain polycyclic ethers and amines: 09COC919. Iodolactonization: Past and present examples: 09COC720. Metal-catalyzed heterocyclization leading to five- and six-membered oxygen heterocycles through C–O bond forming reactions published during 2005 to 2008: 09H(78)2661. Nitroalkanes as key building blocks for the synthesis of heterocyclic derivatives: 09ARK(9)195. Organosilicon compounds as water scavengers in reactions of carbonyl compounds, particularly in their heterocyclizations: 09S3719. Recent advances in the aza-Claisen rearrangement, mainly, in syntheses of various heterocycles: 09S2117. Recent advances in the Pd-catalyzed chemical transformations of Baylis–Hillman adducts, particularly, into heterocyclic compounds: 09T8769. Ring closures to heterocycles via nitrenes: 09COC789. Synthesis of heterocycles in 1,3-dipolar cycloaddition reactions of nitrile oxides: 08MI4. Synthesis of heterocycles in 1,3-dipolar cycloaddition reactions of nitrones: 08MI5. Synthesis of heterocycles in 1,3-dipolar cycloaddition reactions of nitronates: 08MI6. Synthesis of substituted aromatic and heteroaromatic compounds using ruthenium-catalyzed ring-closing metathesis: 09YGK876. Synthetic applications of intramolecular aza-Wittig reaction for heterocyclic compounds: 09COC808. Synthesis of five- and six-membered heterocyclic compounds by the application of the metathesis reactions: 09H(78)1109. Synthesis of heterocycles from 1,2-diaza-1,3-dienes: 09EJO3109. 2.2.4.5. Syntheses by transformation of heterocycles
Chiral Brønsted acid catalyzed Friedel–Crafts alkylation reactions, mainly, of heterocycles: 09CSR2190. Recent advances in aryl–aryl bond formation by direct arylation, particularly, of hetarenes: 09CSR2447. Recent advances in the application of the Sonogashira method in the synthesis of heterocycles: 09T7761.
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Recent advances in the synthesis of (hetero)aryl-substituted heteroarenes via transition metal-catalyzed direct (hetero)arylation of heteroarene C–H bonds with aryl halides or pseudohalides, diaryliodonium salts, and potassium aryltrifluoroborates: 09T10269. 2.2.5. Properties and Applications (Except Drugs and Pesticides) 2.2.5.1. Dyes and intermediates
Merocyanine dyes: synthesis, structure, properties, and applications: 09UK151. Molecular designs and syntheses of organic dyes for dye-sensitized solar cells (coumarin, thiophene-based, indoline, heteropolycyclic, porphyrin, phthalocyanine, and squaraine dyes): 09EJO2903. 2.2.5.2. Substances with luminescent and related properties
The chemistry of fluorescent dipyrrometheneboron difluoride (F-Bodipy) dyes: 08AG(E)1184. Fluorescent labeling of biomolecules with organic probes: 09CRV190. Heavy metal organometallic electrophosphors derived from multicomponent chromophores: 09CCR1709. Light-emitting materials having tunable emission wavelengths (fluorescent organic dyes: coumarin, fluorescein, BODIPY derivatives; novel fluorophore: 1,2-dihydropyrrolo[3,4-b]indolizin-3-one): 09CAJ1646. Light-sensitive heterocyclic compounds for information nanotechnologies: 09ARK(9)70. Long-range electron transfer in artificial systems with d6 and d8 metal (Ru(II), Os(II), Re(I), Ir(III), Ir(I), and Pt(II)) photosensitizers (polypyridine, terpyridine, porphyrin-based complexes): 09CCR1439. Luminescent ruthenium–polypyridine complexes and phosphorus ligands: 09CSR1621. Luminescent metal–organic frameworks: 09CSR1330. Photoactive corrole-based arrays: 09CSR1635. Rational design and functions of N-heterocyclic electron donor–acceptor dyads with much longer charge-separated lifetimes than natural photosynthetic reaction centers: 09BCJ303. Progress in photochromic spiro compounds containing O, N or S: 08CJO1366. Luminescence properties and redox behavior of Ru(II) molecular racks based on polytopic molecular strands made of poly(pyridine–pyrimidine), poly(naphthyridine–pyrimidine), and poly(hydrazone–pyrimidine/pyrazine) subunits: 08CCR2480.
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Development of fluorescent 2-pyrone derivatives using ketene dithioacetals for organic electro luminescent devices: 09H(78)555. Fluorescent amino acids: advances in protein-extrinsic coumarin fluorophores: 09OBC627. Fluorescent switches based on photochromic compounds, including spiropyrans and spiroindolizines: 09EJO2031. McMurry reaction in the synthesis of photochromic dihetarylethenes: 09UK355. Molecular designs, characterizations, and applications of multiphoton absorbing materials (polythiophenes, coordination compounds with pyridine ligands, pophyrins): 08CRV1245. Recent progress on synthesis of fluorescein probes: 09MRO35. Thermodynamic and kinetic analysis of complex formation of photochromic spiropyrans with metal ions: 09IZV1291. 2.2.5.3. Organic conductors
2,1,3-Benzothiadiazole-, thiophene-, thieno[3,4-b]pyrazine-, quinoxaline-, and silole-based conjugated polymers for high-efficiency bulk heterojunction photovoltaic devices: 09ACR1709. Development of high-performance n-type organic field-effect transistors based on nitrogen heterocycles: 09CL870. Electronic and structural factors in modification and functionalization of clean and passivated semiconductor surfaces with aromatic systems (mainly, heterocycle-based): 09CRV3991. Molecular design of organic semiconductors (mostly, tetrathiafulvalene derivatives) for high-performance organic field-effect transistors: 08YGK515. Progress in organic electric or magnetic materials with spiroconjugation effect: 09CJO1192. 2.2.5.4. Coordination compounds
Classification of P,N-binucleating ligands (mainly, heterocycle-based) for hetero- and homobimetallic complexes: 09CCR1793. Complexation and separation of lanthanides(III) and actinides(III) by heterocyclic N-donors in solutions: 08CRV4208. Conformationally gated photoinduced processes within photosensitizer–acceptor dyads based on ruthenium(II) and osmium(II) polypyridyl complexes with an appended pyridinium group: 08CCR2552.
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Coordination chemistry of Robson-type macrocyclic hexamine- dithiophenolate ligands: Syntheses, structures and magnetic properties of dinuclear complexes of first-row transition metals: 09CCR2244. Coordination chemistry of 1,4,7,10-tetraazacyclododecane-N,N′,N″, N′″-tetraacetic acid: 09CCR1906. Dinuclear and polynuclear lanthanide coordination complexes containing polyazine ligands: Synthesis and luminescent properties: 09CCR2627. Electronic absorption spectroscopy of [Ru(phen)2(bpy)]2+, [Ru(phen)2 (dmbp)]2+, [Ru(tpy)(phen)(CH3CN)]2+ and [Ru(tpy)(dmp)(CH3CN)]2+ (phen = 1,10-phenanthroline; bpy = 2,2′-bipyridine, tpy = 2,2′; 6′,6″-terpyridine, dmbp = 6,6′-dimethyl-2,2′-bipyridine, dmp = 2,9-dimethyl-1,10-phenanthroline): A theoretical study: 08CCR2493. Electronic and magnetic properties of bimetallic ytterbocene complexes with bridging polypyridyl ligands: 08CEJ422. From mono to polydentate azole and benzazole derivatives, versatile ligands for main group and transition metal atoms: 09CCR1979. Heteropoly acids as green chemical catalysts in organic synthesis: 08H(76)73. Improving the photophysical properties of copper(I) bis(phenanthroline) complexes: 08CCR2572. Iron(II) complexes of 2,6-di(pyrazol-1-yl)pyridines—A versatile system for spin-crossover research: 09CCR2493. Metallomicelles of metal-complexing amphiphiles (N-heterocycles as ligands) as potent catalysts for the ester hydrolysis reactions in water: 09CCR2133. Metallomicellar supramolecular systems (N-heterocycles as ligands) and their applications in catalytic reactions: 09CCR2166. Metallo-supramolecular block copolymer micelles (polypiridine as ligand): 09CCR2214. Molecular recognition, fluorescence sensing, and biological assay of phosphate anion derivatives using artificial Zn(II)–dipicolylamine complexes: 09CC141. Mononuclear six-coordinated Ga(III) complexes, particularly, with heterocyclic ligands: 09CCR56. New generation of metal string complexes: strengthening metal–metal interaction via naphthyridyl group modulated oligo-α-pyridylamido ligands: 09CC4323. NMR studies on the electronic structure of one-electron oxidized complexes of iron(III) porphyrinates: 09CCR2056.
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Nonmetallocene hydride complexes of the rare earth metals (tris(pyrazolyl) borates, calix-tetrapyrroles, dipyrrolides as ligands): 08CCR1577. Photophysical properties and applications of Re(I) and Re(I)–Ru(II) carbonyl polypyridyl complexes: 08CCR2585. Polynuclear coordination cages containing two chelating pyrazolyl–pyridine units: 09CC4487. Polynuclear metal complexes of ligands containing phenolic units, particularly those bearing various heterocycles as sidearms: 08CCR1121. Polynuclear transition metal complexes of metal...metal-bridging compartmental pyrazolate ligands: 09CCR2698. Recent trends in the chemistry of molecular complexes of heteroaromatic N-oxides: 08H(75)2367. Sawhorse-type diruthenium tetracarbonyl complexes with two terminal two-electron ligands (mainly, N-heterocyclic): 09CCR2639. Spin crossover phenomena in extended multicomponent metallosupramolecular assemblies (bis(bipyridyl)pyrimidine, 2,2′:6′,2″-terpyridine, 2,6-di(pyrazol-1-yl)pyridine ligands): 09CCR2414. Spin crossover complexes with N-heterocycles as ligands and N4O2 coordination sphere—The influence of covalent linkers on cooperative interactions: 09CCR2432. Spin transition in octahedral metal complexes containing tetraazamacrocyclic ligands: 09CCR2450. Spin crossover in iron(II) complexes of 3,5-di(2-pyridyl)-1,2,4-triazoles and 3,5-di(2-pyridyl)-1,2,4-triazolates: 08CCR2072. Stabilization and immobilization of polyoxometalates in porous coordination polymers through host–guest interactions (pyridyl, pyrazinyl, triazole, or imidazole ligands as guests): 09CCR2872. Sterically induced differences in N-heterocyclic carbene transition metal complexes: 09CCR2481. Structures and properties of mercury(II) coordination polymers, mainly, with N-heterocycles as ligands: 09CCR1882. 2.2.5.5. Polymers
Advances in molecular design and synthesis of regioregular polythiophenes: 08ACR1202. Aliphatic and aromatic carboxylate divalent metal coordination polymers incorporating the kinked and hydrogen-bonding capable tethering ligand 4,4′-dipyridylamine: 09CCR1759. Base-pairing mediated noncovalent polymers: 09CSR1608.
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Chain-growth condensation polymerization for the synthesis of welldefined condensation polymers and π-conjugated polymers (polythiophenes and polypyrroles): 09CRV5595. Copper-mediated aryl–aryl couplings for the construction of oligophenylenes and related heteroaromatics: 09ASC984. Development of electron-transporting conjugated oligomers, mostly, oligothiophenes, based on fluorination reactions and their application to organic field-effect transistors: 08YGK504. Electronic and magnetic properties of bimetallic ytterbocene complexes with bridging polypyridyl ligands: 08CEJ422. Fullerene (combined with porphyrin and polythiophene) for organic electronics: 09CSR1587. In situ hydrothermal synthesis of tetrazole coordination polymers with interesting physical properties: 08CSR84. Ladder π-conjugated materials containing main-group elements (poly(2,7-dibenzosilole)s, dibenzophosphole oxide-containing π-conjugated polymers, fused polycyclic heteraborins, phosphole-based π-electron materials, fused oligothiophenes): 09CAJ1386. Monolayers and multilayers of conjugated polymers as nanosized electronic components (pyrrole- and thiophene-based monomers for layers; polythiophene-based multilayers; soluble polythiophenes; polypyrrolebased multilayers): 08ACR1098. Poly(2,7-carbazole)s: Structure–property relationships: 08ACR1110. Poly(2-oxazoline)s (products of cationic ring-opening polymerization of 2-oxazolines): 09AG(E)7978. Progress in studying spiro macromolecular compounds containing O, N and S: 08CJO1287. Semiconductors (soluble oligoacenes, oligo- and polythiophenes and their respective copolymers, and oligo- and polytriarylamines) for solutionprocessable organic field-effect transistors: 08AG(E)4070. Shape-programmable macromolecules. Construction of synthetic building blocks, bis-amino acids, that then undergo coupling through pairs of amide bonds to create water-soluble, spiroladder oligomers (bis-peptides) with well-defined three-dimensional structures: 08ACR1387. Supramolecular polymerization: 09CRV5687. Supramolecular structures and nanoassemblies of tetrathiafulvalene oligomers: 08YGK1211. Synthesis and properties of oligo(2,5-thienylene-ethynylene)s: 09ARK(9)57.
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Synthesis of conjugated polymers (mainly, heterocycle-based) for organic solar cell applications: 09CRV5868. Thiophene polymer semiconductors for organic thin-film transistors: 08CEJ4766. 2.2.5.6. Ionic liquids
Applications of chiral ionic liquids: 08EJO3235. Functionalized chiral ionic liquids as a new type of asymmetric organocatalysts and nonclassical chiral ligands: 09CAJ1184. Halogenation of organic compounds in ionic liquids: 09T5625. Ionic liquids and their interaction with cellulose: 09CRV6712. Ionic liquids as suitable media for organocatalytic reactions: 09EJO321. Ionic liquid-based catalysis with solids: 09ASC817. Ionic liquid lubricants: designed chemistry for engineering applications: 09CSR2590. Progress in the application of ionic liquids to organic synthesis: 08CJO2081. Properties and applications of protic ionic liquids (imidazole, pyrazole, pyrrole, pyridinium derivatives): 08CRV206. Recent advances in the synthesis and application of chiral ionic liquids: 08S999. Task-specific ionic liquids for cellulose technology: 09CL2. Toxicity, biodegradability and design and synthesis of green ionic liquids: 09CJO672. Understanding ionic liquids at the molecular level (methylimidazole, pyrrolidine, pyridazole derivatives): 08AG(E)654. 2.2.5.7. Miscellaneous
Advances in syntheses of carbo- and heterocycles via homogeneous gold catalysis: 08T3885, 08T7847. Anion receptors that contain metals as structural units (metal complexes of O- and N-heterocycles): 09CC513. The Baeyer–Villiger reaction on heterogeneous catalysts: 08T2011. Bistable organic, organometallic, and coordination compounds for molecular electronics and spintronics (O-, N-, and N,O-spiro compounds, azomethynes, azophenoxazines, polythiophenes, porphyrins, phthalocyanines): 08IZV673. Brønsted acid- and Brønsted base-catalyzed Diels–Alder reactions (N-heterocycles as catalysts): 08OBC3229.
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Catalysis of the Claisen rearrangement: 08T597. Catalytic asymmetric reactions using optically active chiral ligands, ferrocenyloxazolinylphosphines: 08SL1747. Chemistry of nitroxyl radicals in molecular design of magnetics: 09UK1051. Conjugated imines and iminium salts as versatile acceptors of nucleophiles in syntheses of N-heterocycles: 09CC874. Cycloaddition of oxidopyrylium species in organic synthesis: 08T3405. Design of two-photon absorbing materials for molecular optical memory and photodynamic therapy: 09OBC2241. Development of N-heterocyclic chiral spiro ligands for metal-catalyzed asymmetric reactions: 09BCJ285. Differentiation of molecular structure of nitro compounds as the base of modeling processes of their thermodestruction: 09UK1022. Discrete cyclic porphyrin arrays as artificial light-harvesting antenna: 09ACR1922. Electrides (ionic solids with cavity-trapped electrons, crown ethers or criptands playing the role of cavity): 09ACR1564). π-Extended porphyrins and unsymmetrical phthalocyanines as potential sensitizers for highly efficient dye-sensitized solar cells: 09ACR1809. Gd−Hydroxypyridinone (HOPO)-based high-relaxivity magnetic resonance imaging (MRI) contrast agents: 09ACR938. Gold-catalyzed reactions of C–H bonds including reactions with participation and formation of heterocycles: 08T4917. Heterocycles as ligands in complexes used as chemosensors for pyrophosphate: 09ACR23. High-relaxivity MRI contrast agents (mainly, gadolinium(III) hydroxypyridinone chelate complexes): 08AG(E)8568. Metal complexes with heterocyclic ligands as potential catalysts for the photocatalytic reduction of carbon dioxide for solar fuels: 09ACR1983. Modern reaction-based indicator systems (heterocycles as indicators): 09CSR1647. Molecular bulk heterojunctions using 3D donors like twisted bithiophene and borondipyrromethene (BODIPY) as an emerging approach to organic solar cells: 09ACR1719. Neutral tridentate pyridine-based PNP ligands and their hybrid analogues as versatile scaffolds for homogeneous catalysis: 09AG(E)8832. A new trend in rhodamine-based chemosensors: application of spirolactam ring opening to sensing ions: 08CSR1465.
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Organic catalysis of asymmetric aldol reaction. Catalysts and reagents: 09UK796. Organic chemistry of fullerenes: main reactions and types of fullerene compounds, prospects of their practical use: 08UK323. Organic synthesis “On water” (including synthesis of heterocycles): 09CRV725. Organocatalytic asymmetric Michael additions: 09CJO1018. Phosphonium salt organocatalysis: 09ASC1469. Physico-chemical aspects of metals protection using corrosion inhibitors from azole series: 08UK227. Polymer-supported well-defined metathesis catalysts (particularly, immobilized using pyridine or N-heterocyclic carbenes): 09CRV303. Progress in research on molecular machines: 08CJO2057. Recent applications of click chemistry for the synthesis of radiotracers for molecular imaging: 09MRO21. Recyclable stereoselective catalysts (a general review): 09CRV418. Routes to photoreversible magnets (photochromic compounds with heterocyclic fragments): 08IZV704. The salt made from 9-amino-9-deoxy-epi-hydroquinine and N-Boc-dphenylglycine as a novel organocatalyst for the iminium activation of α,βunsaturated ketones: 08SL1759. Solid-state photophysical properties and functional characteristics of heterocyclic quinol-type fluorescent hosts with clathrate-forming ability: 09YGK337. Synthesis of heterocyclic 18F, 15O, and 13N radiolabels for positron emission tomography: 08AG(E)8998. Using soluble polymer supports to facilitate homogeneous catalysis (various heterocyclic ligands): 09CRV530.
2.3. Specialized Heterocycles 2.3.1. Nitrogen Heterocycles (Except Alkaloids) 2.3.1.1. General sources and topics
Anion–π interactions, particularly, in triazines and other N-heterocycles: 08CSR68. Bicyclic guanidines, guanidinates and guanidinium salts: 09CC3659. Cage N-heterocycles: 09MI3. Click reactions and asymmetric organocatalysts of polynitrogen compounds: 08CJO361. “Green” pyrotechnics (nitrogen-rich energetic materials, such as tetrazole and tetrazine derivatives): 08AG(E)3330.
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Lactam acetals: 09MI4. N-Heteroacenes: 09CEJ6780. Nitrogen-containing organofluorine derivatives (including pyrimidine, indoline, pyrazole, β- and γ-lactam derivatives): 09SL525. Reactions of early transition metal–carbon bonds with N-heterocycles: 08COC1388. 2.3.1.2. Structure and stereochemistry
Abnormal, remote, and other classes of N-heterocyclic carbenes as ligands with reduced heteroatom stabilization: 09CRV3445. 13C NMR spectroscopy of “Arduengo-type” nucleophilic diaminocarbenes and their derivatives: 09CRV3385. Coinage metal–N-heterocyclic carbene complexes: 09CRV3561. F-Block N-heterocyclic carbene complexes: 09CRV3599. Stable heavier carbene analogues including N-, P-, and O-heterocyclic ones: 09CRV3479. Understanding the M–(NHC) (NHC is an N-heterocyclic carbene) bond: 09CCR687. 2.3.1.3. Reactivity
1-Azadienes in cycloaddition and multicomponent reactions toward N-heterocycles: 08CC5474. Complexes with poly(N-heterocyclic carbene) ligands. Structural features and catalytic applications: 09CRV3677. Molecular catalysis of electrochemical reactions of porphyrins, polypyridines, and azamacrocycles: 08CRV2348. N-Heterocyclic carbenes in late transition metal catalysis: 09CRV3612. Ruthenium-based olefin metathesis catalysts bearing N-heterocyclic carbene ligands: 09CRV3708. 2.3.1.4. Synthesis
Carbon–nitrogen bond-forming reactions of dialkyl azodicarboxylate, particularly, to give nitrogen heterocycles: 08CAJ810. Catalytic radical cyclization of oximes to N-heterocycles induced by one-electron transfer: 08BCJ539. Cyclothiomethylation of primary amines with formaldehyde and hydrogen sulfide to give nitrogen- and sulfur-containing heterocycles: 09KGS1443.
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The enantioselective intramolecular aminative functionalization of unactivated alkenes, dienes, allenes and alkynes for the synthesis of chiral nitrogen heterocycles: 09OBC3009. Fluoroarenes in the synthesis of benzoannulated nitrogen-containing heterocycles: 08IZV931. Hydroamination: direct addition of amines to alkenes and alkynes (particularly, synthesis of N-heterocycles): 08CRV3795. Mitsunobu reaction in the chemistry of nitrogen-containing heterocyclic compounds, formation of heterocyclic systems: 08KGS347. More sustainable approaches for the synthesis of N-based heterocycles: 09CRV2703. New strategies for sulfate-free synthesis of lactams from cycloalkanes: 08YGK1066. aza-Baylis–Hillman reaction (mainly, applications for the synthesis of heterocycles): 09CRV1. Preparation of chiral diamines, in particular, cyclic diamines as imidazolines and piperazines by the diaza-Cope rearrangement: 08AA77. Progress in the synthesis of nitrogen-containing heterocycles by intramolecular cyclization of alkynes: 09CJO1924. Stereoselective synthesis of α-aminophosphonic acids and derivatives including aziridin-2-yl-, azetidin-2-yl-, pyrrolidin-2-yl-, piperidin2-ylphosphonic acids and their derivatives: 09T17. Synthesis of nitrogen heterocycles utilizing molecular nitrogen as a nitrogen source and attempt to use air instead of nitrogen gas: 09H(78)281. 2.3.2. Oxygen Heterocycles Cyclic anhydrides in formal cycloadditions and multicomponent reactions: 09CRV164. Efficient methods for the synthesis of polycyclic ethers and their application: 08YGK344. The hetero-Diels–Alder approach to spiroketals: 09OBC1053. Lewis base-catalyzed, stereoselective tandem aldol β- and γ-lactonizations: 08H(76)949. Progress in the synthetic methods of fluorine-containing lactones: 09CJO1728. Synthesis of spirocyclic ethers: 09S2651.
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2.3.3. Sulfur Heterocycles Mechanism and application of the Newman-Kwart O→S rearrangement of O-aryl thiocarbamates, particularly, in the synthesis of S-heterocycles: 08S661. One-pot synthesis of sulfur heterocycles (1,2-dithioles, 1,2,3,4,5-pentathiepins, 1,2,3-dithiazoles, 1,4-thiazines, 1,2,3,4,5,6,7-heptathiocanes) from simple organic substrates and S2Cl2: 09ARK(1)129. New developments in the synthesis of saccharin-related five- and sixmembered benzosultams: 09H(78)1387.
2.4. Natural and Synthetic Biologically Active Heterocycles We have classified the many reviews dealing with these materials under following headings: 1. G eneral Sources and Topics (it is self-subdivided into Biological Functions, Syntheses). 2. A lkaloids (General, Syntheses, Individual Groups). 3. A ntibiotics (Antitumor, Miscellaneous). 4. V itamins. 5. D rugs (General, Activity Types, Individuals and Groups). 6. P esticides. 7. M iscellaneous (Enzymes, Amino Acids and Peptides, Plant Metabolites, Marine, Other). 2.4.1. General Sources and Topics Physiological role, structure and catalytic mechanism of dUTPases: 09ACR97. Positron emission tomography imaging of biomolecules for future diagnostics and exploration of in vivo dynamics: 08OBC815. Small-molecule N-heterocycles as fluorescent sensors for investigating zinc metalloneurochemistry: 09ACR193. 2.4.1.1. B iological functions of natural and synthetic bioactive heterocycles
The Azadirachtin story (azadirachtin is O-heterocyclic compound): 08AG(E)9402. Biological activity of metal ions complexes of chromones, coumarins and flavones: 09CCR2588. Chemistry, biology, and medicinal potential of narciclasine (2,3,4,7tetrahydroxy-3,4,4a,5-tetrahydro-(1,3)dioxolo[4,5-j]phenanthridin-6 (2H)-one) and its congeners: 08CRV1982.
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Genome mining for novel natural product discovery: 08JMC2618. Identification of the cellular targets of bioactive small organic molecules using affinity reagents: 08CSR1347. Natural products as chemical instruments to apprehend some biological problems: 08OBC424. Polychromophoric metal complexes with heterocyclic ligands for generating the bioregulatory agent nitric oxide by single- and two-photon excitation: 08ACR190. Progress in the studies on biological activities of natural spiroketal compounds: 09CJO1508. Progress in the studies on biological activities of O, N or S-containing spiro compounds: 08CJO1501. Small molecule modulators of toll-like receptors: 08JMC6621. 2.4.1.2. G eneral approaches to syntheses of biologically active heterocycles
Acyllactams in the synthesis of physiologically active substances: 09UK466. Advances in solution- and solid-phase synthesis toward the generation of natural product-like libraries: 09CRV1999. Advances of synthesis and structure modification and bioactivity (mainly, as insect antifeedant) of azadirachtin: 09CJO20. Application of donor/acceptor-carbenoids to the synthesis of natural products: 09CSR3061. The art of total synthesis through cascade reactions: 09CSR2993. Asymmetric vinylogous Mukaiyama aldol reactions using vinylketene N,O-acetals in total syntheses of natural products: 08MRO1. Bond formations by intermolecular and intramolecular trappings of acylketenes and their applications in natural product synthesis: 09CSR3022. Chemical properties of cyanoacetanilides and synthesis of biologically active compounds: 08ZOR1591. Construction of architecturally complex natural products possessing the ubiquitous cis-2,6-substituted tetrahydropyran structural element: 08ACR675. Construction of polycyclic natural products by use of transannulation reactions across medium and large rings: 09S691. Cyclization and cycloaddition reactions of cyclopropyl carbonyls and imines including those leading to heterocycles, particularly, natural products: 09S3353.
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Cycloaddition methodology: A useful entry toward biologically active heterocycles: 09COC422. DBU-promoted elimination reactions of vicinal dibromoalkanes mediated by adjacent O-functional groups, and applications to the synthesis of biologically active natural products (mainly, O-heterocycles): 08SL3091. Di-tert-butylsilylene effect as the unique sterically driven director for α-galactosylation: 08H(76)883. Diversity-oriented synthesis of small molecules in the search of novel biologically active lead compounds: 08OBC1149. The economies of synthesis of natural products: 09CSR3010. Efficient total synthesis of novel bioactive microbial metabolites (pyripyropenes, arisugacins, lactacystin, macrosphelides, madindolines, and neoxaline): 08ACR302. Epoxide-opening cascades in the synthesis of polycyclic polyether natural products: 09AG(E)5250. Heterocycles from cyclopropanes: applications in natural product synthesis: 09CSR3051. Hydrolytic kinetic resolution as an emerging tool in the synthesis of bioactive molecules: 09SL1367. 2-Isocyanatobenzonitrile and 2-isothiocyanatobenzonitrile—Versatile building blocks in organic synthesis including one-pot cyclizations to give pharmacologically important heterocycles: 09COC955. Meldrum`s acid and related compounds in the synthesis of natural products and analogs (review covers all relevant literature from 1991 to August 2007): 08CSR789. Metal-catalyzed enantioselective allylation in asymmetric synthesis of natural products and other chiral compounds: 08AG(E)258. Microwave-assisted Claisen and aza-Claisen rearrangements for the synthesis of heterocyclic and natural compounds: 08MRO85. Natural product synthesis using multicomponent reaction strategies: 09CRV4439. The oxa-Michael reaction: from recent developments to applications in natural product synthesis: 08CSR1218. Palladium(II)-catalyzed cyclization via N-alkylation of an allyl alcohol with a urethane and its application to the syntheses of natural products: 08H(75)2133. Palladium-mediated intramolecular biaryl coupling reaction for natural product synthesis: 08H(75)1021. Potential of amino acid-derived α-aminonitriles in the preparation of peptidomimetics: 08MRO209.
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Rapid formation of complexity in the total synthesis of natural products enabled by oxabicyclo[2.2.1]heptene building blocks: 09CSR3222. Recent advances in the Mitsunobu reaction: Modifications and applications to biologically active molecules: 09COC1610. Recent advances in monosaccharide synthesis: A journey into the L-hexose world: 09COC71. Recent advances in the syntheses of biologically active natural products using biocatalysts: 09H(78)1667. Recent advances of bismuth(III) salts in organic chemistry: Application to the synthesis of heterocycles of pharmaceutical interest: 09COS426. Recent applications of microwaves in the synthesis of bioactive heterocyclic compounds: 08COC836. Recent approaches in the synthesis of conformationally restricted nucleoside analogues: 08EJO1489. A retrospective on the design and synthesis of novel molecules, particularly, of natural products through a strategic consideration of metathesis and Suzuki–Miyaura cross-coupling: 09CAJ354. Samarium diiodid- mediated reactions in total synthesis: 09AG(E)7140. Recent applications of intramolecular Diels–Alder reactions to natural product synthesis: 09CSR2983. [3,3]-Sigmatropic rearrangements: recent applications in the total synthesis of natural products: 09CSR3133. Stereocontrolled preparation of fully substituted cyclopentanes: Relevance to total synthesis, particularly, of natural products: 09EJO1477. Stereoselective reaction for the construction of a quaternary carbon center and its application to the syntheses of pyrrolidino[2,3-b]indoline natural products: 09YGK1012. Stereoselective synthesis of highly functionalized spirocyclic compounds based on a Claisen rearrangement and its application to the synthesis of natural products: 08YGK124. The syntheses and applications of β-benzylmercaptoethylamine derivatives, particularly, in the chemistry of heterocycles and natural products: 09T10515. Synthesis of biologically active guaianolides with a trans-annulated lactone moiety: 08EJO2353. Synthesis of natural product inspired compound collections: 09AG(E)3224. Synthesis of trifluoromethyl-containing pyridines and their applications to biologically active molecules: 09YGK992.
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Synthetic approaches to the bicyclo[2.2.2]diazaoctane ring system common to the paraherquamides, stephacidins and related prenylated indole alkaloids: 09CSR3160. Synthetic philosophy in syntheses of heterocycles, mainly, potential drugs: 08H(75)1021. Synthetic study of linderol A, a potent inhibitor of melanin biosynthesis: 08YGK61. Synthetic studies on shellfish toxin azaspiracid-1: 08YGK836. Thiol-mediated radical cyclizations to form carbo- and heterocycles including natural products: 08T9799. Using singlet oxygen to synthesize polyoxygenated natural products from furans: 08ACR1001. 2.4.2. Alkaloids 2.4.2.1. General
A brief history of the isolation, study of biological properties and mechanism of action of the marine polyether biotoxins: 08AG(E)7182. Catalytic, asymmetric reactions of ketenes and ketene enolates, particularly, β-lactone synthesis with Cinchona alkaloids as catalysts: 09T6771. The nomofungin/communesin/perophoramidine (alkaloids) story: 08AG(E)8170. A SAR/QSAR study of alkaloids camptothecins: 09CRV213. 2.4.2.2. Structure
Development of reductive photocycloaddition reaction of enamides, radical addition, and nucleophilic addition reactions and their application to the synthesis of yohimbine, heteroyohimbine, ergot, pseudodistomin, and isositsirikine alkaloids: 08CPB1367. 2.4.2.3. Synthesis
Arthropod alkaloids in poison frogs: A review of the “Dietary hypothesis”: 09H(79)277. Asymmetric syntheses of oxindole and indole spirocyclic alkaloid natural products: 09S3003. Aza-annulation strategies in alkaloid total synthesis: 08S331. Biogenetically inspired syntheses of alkaloid natural products: 09CSR3035. Building bicyclic polyhydroxylated alkaloids: An overview from 1995 to the present: 08COC718.
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Copper-catalyzed cyclization reactions for the synthesis of alkaloids: 09CC4166. Design, syntheses and applications of oxazole- and imidazole-containing macrocyclic pseudopeptide platforms related to Lissoclinum alkaloids: 09SL3082. The development of asymmetric primary amine catalysts based on Cinchona alkaloids: 08SL1919. Discovery of the frog alkaloid batrachotoxin: 09H(79)195. Domino reactions of rhodium(II) carbenoids for alkaloid synthesis: 09CSR3072. Epibatidine: From frog alkaloid to analgesic clinical candidates: 09H(79)207. Epibatidine analogs synthesized for characterization of nicotinic pharmacophores: 09H(79)99. (-)-Indolizidine 167B via 4-pyrrolylbutanals:Two synthetic methodologies at comparison: 09H(79)219. Gold and platinum catalysis as a convenient tool for generating molecular complexity (particularly, alkaloid syntheses): 09CSR3208. Multicomponent cycloaddition approaches in the catalytic asymmetric synthesis of alkaloids: 09CSR3149. Oxidative dearomatization of phenols, particularly, in alkaloid synthesis: 08SL467. Progress in the synthesis of anticancer indolizidine alkaloid swainsonine: 09CJO689. Progress in the synthesis of pyrroloquinazolinoquinoline alkaloid luotonin A and its derivatives: 09CJO1533. Progress in the total synthesis of swainsonine: 09CJO1354. Recent advances in the synthesis of lamellarins as anticancer alkaloids: 09CJO867. Recent strategies for the synthesis of protoberberines and protoberberine type compounds: 09COC353. Recent synthetic developments in a powerful imino Diels–Alder reaction (Povarov reaction): application to the synthesis of N-polyheterocycles and related alkaloids: 09T2721. Stereocontrolled cyclic nitrone cycloaddition strategy for the synthesis of pyrrolizidine and indolizidine alkaloids: 09CEJ7808. Stereoselective syntheses of 2,6-disubstituted piperidin-3-oles (alkaloid lipids): 08COC1454. Strategies for the synthesis of Stemona alkaloids: 09EJO2421.
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Syntheses of apogalanthamine analogues and 7-aza derivatives of steganacin and steganone (Amaryllidaceae alkaloid analogues with a 5,6,7,8-tetra hydrodibenz[c,e]azocine skeleton): 08EJO5867. Syntheses of bromopyrrole alkaloids, manzacidins: 08OBC829. Chemoselectivity: The mother of invention in the total synthesis of alkaloids: 09ACR530. Synthesis of biologically active carbazole alkaloids using selective transition-metal-catalyzed coupling reactions: 09CL8. Synthetic approaches to the bicyclo[2.2.2]diazaoctane ring system common to the paraherquamides, stephacidins and related prenylated indole alkaloids: 09CSR3160. Synthetic methods of lycopodine, the first discovered among licopodium alkaloids: 08CJO755. Synthetic studies toward the Martinella alkaloids: 08COC1431. Total synthesis and study of myrmicarin alkaloids: 09CC4151. Total synthesis of incarvillateine and related alkaloids: 09YGK369. Total synthesis of vindoline and related alkaloids: 09YGK123. 2.4.2.4. Individual groups of alkaloids
The biology and chemistry of the zoanthamine alkaloids: 08AG(E)2365. The Daphniphyllum alkaloids: 09COC646. The Lycopodium alkaloids (data reported in the literature from 2004 to July 2008): 09H(77)679. Progress in the studies on alkaloids from endophytic fungi: 09CJO1182. 2.4.3. Antibiotics
2.4.3.1. Antitumor antibiotics
Epothilones as lead structures for the synthesis-based discovery of new chemotypes for microtubule stabilization: 08ACR21. Recent progress in the total synthesis of naphthyridinomycin and lemonomycin tetrahydroisoquinoline antitumor antibiotics: 08CSR2676. 2.4.3.2. Miscellaneous antibiotics
The chemical versatility of natural product assembly lines, in particular, principles of synthesis of rebeccamycin, vancomycin, bleomycin, daptomycin and other glicopeptide antibiotics: 08ACR4. New strategies and methods in the discovery of natural product antiinfective agents: The mannopeptimycins: 08JMC2613. Recent progress in the total synthesis of lactone antibiotic brefeldin A: 09CJO206.
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Syntheses of peptidyl nucleoside antibiotics: 09H(77)67. Synthesis of antibiotic platensimycin: 08AG(E)2548. Total synthesis of nucleoside antibiotics possessing novel N-glycoside structures: 08YGK1105. 2.4.4. Vitamins Synthesis of 1α,25-dihydroxy-2β-(3-hydroxypropoxy)vitamin D3 (Eldecalcitol) and related compounds by the Trost convergent methodology: 09H(79)145. Thiamin diphosphate catalysis: Enzymic and nonenzymic covalent intermediates: 08CRV1797. Vitamin B12 and a-ribonucleosides: 08T9. 2.4.5. Drugs
2.4.5.1. General
Adenosine receptor antagonists: Translating medicinal chemistry and pharmacology into clinical utility: 08CRV238. Aqueous microwave chemistry: a clean and green synthetic tool for rapid drug discovery: 08CSR1546. The challenge of atropisomerism in drug discovery: 09AG(E)6398. Covalent modifiers: An orthogonal approach to drug design: 09JMC1231. The development of bisphosphonates for therapeutic uses, and bisphosphonate structure–activity consideration: 09ARK(9)143. Fundamental relationships between structure, reactivity, and biological activity for the duocarmycins and CC-1065: 09JMC5771. Inhibitors of HIV-1 integrase as a new component of antiviral therapy: 08UK445. Knowledge-based prediction of ligand binding modes and rational inhibitor design for kinase drug discovery: 08JMC5149. The many roles for fluorine in medicinal chemistry: 08JMC4359. The medicinal applications of imidazolium carbene–metal complexes: 09CRV3859. Nicotinic acid receptor agonists: 08JMC7653. Polyfunctional compounds containing organic nitrate moieties as prototypes of hybrid drugs: 09UK442. Recent developments in fragment-based drug discovery: 08JMC3661. Synthesis of chiral pharmaceutical intermediates by biocatalysis: 08CCR659.
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Thalidomide as a multitemplate for development of biologically active compounds (thalidomide—2-(2,6-dioxopiperidin-3-yl)-1H-isoindole-1,3(2H)dione): 08AP536. Toward the optimal screening collection: A synthesis strategy of drugs creation: 08AG(E)48. Toxicology of drugs: 09MI5. 2.4.5.2. Definite types of activity
Advances in HIV-1 integrase inhibitors directed toward different steps of integration: 09CJO536. Advances in synthetic approaches for the preparation of combretastatinbased anticancer agents: 09S2471. Allosteric modulators of the α7 nicotinic acetylcholine receptor: 08JMC701. The anticancer properties of gold(III) compounds with dianionic porphyrin and tetradentate ligands: 09CCR1682. Antimalarial drugs: 08AP149. Antioxidant, antiinflammatory and antiinvasive activities of biopolyphenolics and some O- and N-heterocyclic compounds: 08ARK(6)119. Biomedical application of orexin/hypocretin receptor ligands in neuroscience: 09JMC891. Chemistry and biology of synthetic and naturally occurring antiamoebic agents: 09CRV1900. Chemistry of trisdecacyclic pyrazine antineoplastics: 09CRV2275. 1,3-Dipolar cycloadditions: applications to the synthesis of antiviral agents: 09OBC4567. Discovery and combinatorial synthesis of fungal metabolites beauveriolides, novel antiatherosclerotic agents: 08ACR32. Discovery and development of aurora kinase inhibitors as anticancer agents: 09JMC2629. The discovery of antibacterial agents using diversity-oriented synthesis: 09CC2446. The discovery of taranabant (N-[(1S,2S)-3-(4-chlorophenyl)-2(3-cyanophenyl)-1-methylpropyl]-2-methyl-2-(5-(trifluoromethyl)pyridin2-yloxy)propanamide), a selective cannabinoid-1 receptor inverse agonist for the treatment of obesity: 08AP405. Emerging opportunities for antipsychotic drug discovery in the postgenomic era: 08JMC1077. Enzymology of purine and pyrimidine antimetabolites used in the treatment of cancer: 09CRV2880.
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Gold complexes with N-heterocycles as potential antiparasitic agents: 09CCR1619. Harnessing nature’s insight: Design of aspartyl protease inhibitors from treatment of drug-resistant HIV to Alzheimer’s disease: 09JMC2163. Hedgehog–Gli signaling pathway inhibitors as anticancer agents: 09JMC3829. Hybrid molecules with a dual mode of action: trioxaquines, prospective new antimalarial drugs possessing a trioxane motif covalently linked to an aminoquinoline entity: 08ACR69. Imidazole derivatives and their antitumor activity: 06KFZh(8)12. Inhibition of the insulin-like growth factor-1 receptor (IGF1R) tyrosine kinase as a novel cancer therapy approach: 09JMC4981. Inhibitors of phosphoinositide-3-kinase: a structure-based approach to understand potency and selectivity: 09OBC840. Linezolid (ZYVOX, (S)-N-{3-[3-fluoro-4-(morpholin-4-yl)phenyl]2-oxo-1,3-oxazolidin-5-yl}methyl acetamide), the first member of a completely new class of antibacterial agents for treatment of serious grampositive infections: 08JMC1981. Microsomal prostaglandin E2 synthase-1 (mPGES-1): A novel antiinflammatory therapeutic target: 08JMC4059. Modern approaches to construction of stimulators of memory and cognitive functions based on ligands of AMRA receptors: 09UK524. Multitarget-directed ligands to combat neurodegenerative diseases: 08JMC347. Natural and synthetic compounds with an antimycobacterial activity: 09MRO135. Natural products, small molecules, and genetics in tuberculosis drug development: 08JMC2606. A new class of antiviral compounds, azolo[5,1-c]-1,2,4-triazines: 08IZV967. Recent advances on phosphodiesterase 4 inhibitors for the treatment of asthma and chronic obstructive pulmonary disease: 08JMC5471. Recent developments of carbonic anhydrase inhibitors as potential anticancer drugs: 08JMC3051. Structure- and mechanism-based design and discovery of therapeutics for cocaine overdose and addiction: 08OBC836. Therapeutics for the treatment of atherosclerosis: 09T433. The translocator protein (18 kDa): Central nervous system disease and drug design: 09JMC581.
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2.4.5.3. Individual substances and groups of compounds
Recent developments on clinical applications of 3-hydroxy-4-pyridinones: 08CCR1213. Salvinorin A analogs as probes in opioid pharmacology (Salvinorin A is a natural diterpene with O-heterocyclic fragments): 08CRV1732. Thiosemicarbazones from the old to new: Iron chelators that are more than just ribonucleotide reductase inhibitors: 09JMC5271. Trans geometry in platinum antitumor complexes: 08CCR1328. 2.4.6. Pesticides Molecular recognition of neonicotinoid insecticides: 09ACR260. Research advances in synthesis and antifungal activity of pyrimidine compounds: 09CJO365. 2.4.7. Miscellaneous
2.4.7.1. Enzymes, coenzymes, and their models
Antagonists of the P2X7 receptor. From lead identification to drug development: 09JMC3123. Chemistry and biology of the aeruginosin family of serine protease inhibitors: 08AG(E)1202. Functional biomimetic models for the active site in the respiratory enzyme cytochrome c oxidase: 08CC5065. Histone deacetylase inhibitors: 08JMC1505. Nonpeptide gonadotropin-releasing hormone receptor antagonists: 08JMC3331. Recent progress in indolylmaleimide derivatives as protein kinase C inhibitors: 08CJO1676. Ruthenium-catalyzed biomimetic oxidation in organic synthesis inspired by cytochrome P-450: 08CSR1490. Structure, mechanism, and inhibition of inosine monophosphate dehydrogenase (IMPDH): 09CRV2903. Synthetic strategies of nonpeptidic β-secretase (BACE1) inhibitors: 09JHC10. Synthesis of glycosyltransferase inhibitors: 09S3179. 2.4.7.2. Amino acids and peptides
Beyond the Ugi reaction: less conventional interactions between isocyanides and iminium species: 09T2153. Chemistry of norbornane/ene and heteronorbornane/ene β-amino acids: 08COS173.
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Chiral acylation with N-(protected α-aminoacyl)benzotriazoles for advantageous syntheses of peptides and peptide conjugates: 09SL2392. Ionic liquids: New targets and media for α-amino acid and peptide chemistry: 08CRV5035. Metathesis in peptides and peptidomimetics: 08ASC(350)1661 Progress in synthesis of cyclopeptides: 08CJO549. Ring constraint in peptidomimetics using bicyclic and polycyclic amino acids: 08ACR1241. Utilization of N,N,N′,N′-tetramethylfluoroformamidinium hexafluorophosphate (TFFH) in peptide and organic synthesis: 09SL886. 2.4.7.3. Plant metabolites
Chemistry and biology of mycotoxins and related fungal metabolites: 09CRV3903. The diterpenoids from the genus hyptis (Lamiaceae): 09H(78)1413. Plant orthoesters: 09CRV1092. Progress in ent-abietane euphorbiae diterpene lactones: 09CJO188. Recent advances in the total synthesis of xanthanolide sesquiterpenoids: 09H(78)873. Strategies for the total synthesis of C2–C11 cyclized cembranoids: 08CRV5278. Survey of briarane-type diterpenoids: 08H(75)2627. 2.4.7.4. Heterocycles produced by marine organisms
Aaptamine and related products (marine alkaloids containing a benzo[de] [1,6]-naphthyridine framework): their isolation, chemical syntheses, and biological activity: 09T4257. Biologically active marine natural products: 09H(78)1. Lamellarins and related pyrrole-derived alkaloids from prosobranch mollusks: 08CRV264. Recent progress in synthesis of three classes of secondary metabolites obtained from marine fungi from the south China sea coast: 09CJO341. Recent research progress in lamellarin D and its derivatives: 08CJO797. Structural features of marine dinoflagellate toxins underlying biological activity as viewed by NMR: 08BCJ307. Synthesis of the complex marine furanocembranolide providencin: 09SL1357. Variolins and related marine alkaloids: 09CRV3080.
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2.4.7.5. Other topics
Advances in the synthesis of natural butane and butenolides: 09UK364. l-Ascorbic acid in organic synthesis: 09COC99. Bacterial siderophores containing a thiazoline ring: 09MRO120. Bryophytes: Bio- and chemical diversity, bioactivity and chemosystematics: 09H(77)99. Chemistry and structural determination of botcinolides, botcinins, and botcinic acids: 09CC385. Constituents and bioactivities of Clausena excavate: 09H(79)121. Design and synthesis of ladder-shaped polyethers and evaluation of the interaction with transmembrane proteins: 09YGK1250. Eumelanins (products of the oxidative polymerization of 5,6-dihydroxyindoles as unexplored bio-optoelectronic materials): 09AG(E)3914. Fifteen years of biological and synthetic studies of 10-membered lactones, decarestrictine family: 08T2279. The impact of flavonoids on memory: physiological and molecular considerations: 09CSR1152. Inhibition of protein–protein interactions using designed molecules: 09CSR3289. Low-molecular inhibitors of various components of signal cascade transcription factor NF-kB: 08UK1036. d-Luciferin [(S)-2-(6-hydroxybenzothiazol-2-yl)thiazoline-4-carboxylic acid], derivatives and analogues: synthesis and in vitro/in vivo luciferase-catalyzed bioluminescent activity: 09ARK(1)265. Molecular recognition of pertechnetate and perrhenate using artificial heterocycles as receptors: 09CSR1572. Naturally occurring iridoids, secoiridoids and their bioactivity: 09CPB765. Production of unnatural bioactive glycosides using plant secondary product glycosyltransferases: 09H(77)645. Progress toward the total synthesis of the bioactive calothrixins A and B (metabolites from cyanobacteria Calothrix sp.): 09H(77)85. Reactions and uses of artificial ketoses: 09H(79)163. Secondary metabolites from cyanobacteria: 08COC326. Strategies for the synthesis of the cyclopropyl-substituted lactone family of oxylipins: 09SL1713. Synthetic utilizations to 1′-C-methylsaccharides and related carbohydrates: 09H(78)19.
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3. T HREE-MEMBERED RINGS 3.1. General Topics Advances in asymmetric epoxidation of α,β-unsaturated carbonyl compounds: The organocatalytic approach: 08COS117. Asymmetric epoxidation of electron-deficient olefins: 08COS186. Circular dichroism and absorption spectroscopy for oxirane, thiirane, and their derivatives using symmetry-adapted cluster–configuration interaction (SAC-CI) method: 09BCJ1215. Hydrogen bond-mediated asymmetric catalysis using aziridines, and epoxides among “privileged” functional groups in the design of organocatalysts: 08CAJ516. Organocatalytic formation of quaternary stereocenters, particularly, in nucleophilic aziridine ring opening, epoxidation reactions and N-heterocyclic carbene catalysis: 09S1583. Three-membered azaheterocycles based on α,β-unsaturated ketones: 08COC792.
3.2. One Heteroatom 3.2.1. One Nitrogen Atom Cyclization reactions for the stereoselective aziridination via selenonium and telluronium ylides: 09CJO309. Catalytic asymmetric aziridination with catalysts derived from VAPOL and VANOL: 09SL2715. Cycloaddition of silylmethyl-substituted aziridinyl ring systems with dipolarophiles: 08CC6471. A masked 1,3-dipole revealed from aziridines: 09AG(E)9026. 3.2.2. One Oxygen Atom
3.2.2.1. Reactivity of oxiranes
Development and synthetic application of epoxysilane rearrangement: 08YZ1169. The development of endo-selective epoxide-opening cascades in water: 09CSR3175. Development of epoxysilane rearrangement and its application to chirality transfer: 09H(78)2919. Enantioselective ring opening of meso-epoxides: 09YGK76.
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α-Ferrocenyl epoxides: 05SL1863. Methods and mechanisms of reduction of epoxide compounds: 08ZOR167. Reactivity versus stability of oxiranes under palladium-catalyzed reductive conditions: 09EJO961. Regio- and stereoselective ring opening of allylic epoxides: 09COS290. α-Substituted α-lithiated oxiranes as useful reactive intermediates: 08CRV1918. 3.2.2.2. Synthesis of oxiranes
Advances in copper-catalyzed oxidation of organic compounds, particularly, epoxidation: 08CCR134. Asymmetric epoxidation of unsaturated hydrocarbons catalyzed by ruthenium complexes: 08CCR176. Chiral oxoperoxomolybdenum(VI) complexes for enantioselective olefin epoxidation: 08CCR170. Cyclization reactions for the stereoselective epoxidation via selenonium and telluronium ylides: 09CJO309. Organocatalytic oxidation. Asymmetric epoxidation of olefins catalyzed by chiral ketones and iminium salts: 08CRV3958. Synthesis and elaboration of trans 2,3-diaryloxiranes: 08ARK(8)150. Tandem reactions for streamlining synthesis: Enantio- and diastereoselective one-pot generation of functionalized epoxy alcohols: 08ACR883. Total synthesis of epoxyquinols: 09YGK102. 3.2.3. One Sulfur Atom Electrophilic addition and cyclization reactions of allenes to give, particularly, thiiranes: 09ACR1679.
3.3. Two Heteroatoms Development of new method for molecular biology using the photophore, diazirine: 08YZ1615. Synthesis of monocyclic diaziridines and their fused derivatives: 08ARK(1)128. Recent progress in diazirine-based photoaffinity labeling: 08EJO2513.
4. FOUR-MEMBERED RINGS 4.1. General Topics The mechanism of the ketene–imine (Staudinger) reaction to give β-lactams: 08ACR925.
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4.2. One Heteroatom 4.2.1. One Nitrogen Atom Azetidines: New tools for the synthesis of nitrogen heterocycles: 09SL3053. Cycloaddition of silylmethyl-substituted azetidinyl ring systems with dipolarophiles: 08CC6471. Novel syntheses of azetidines and azetidinones: 08CRV3988. Preparation of β-lactams by [2 + 2] cycloaddition of ketenes and imines: 08T10465. Progress in preparation of chiral azetidines and their use as catalysts in asymmetric reactions: 09CJO1059. Recent progress in the asymmetric synthesis of α-azetidinones: 08CJO1. Stereoselectivity in the synthesis of 2-azetidinones from ketenes and imines via the Staudinger reaction: 09ARK(9)21. Synthesis and reactivity of 3-haloazetidines and 3-sulfonyloxyazetidines: 09COC827. Syntheses and transformations of 2-alkylideneaziridines and 2-alkylideneazetidines: 09COC852. An update on the synthesis of β-lactams: 09COS325. 4.2.2. One Oxygen Atom Selective olefination with ynolates (β-lactone enolates as intermediates): 08YGK28.
4.3. Two Heteroatoms The reaction of singlet oxygen with enecarbamates: A mechanistic playground for investigating chemoselectivity, stereoselectivity, and vibratioselectivity of photooxidations (particularly, dioxetane formation): 08ACR387.
5. FIVE-MEMBERED RINGS 5.1. General Topics Catalytic asymmetric hydrogenation of 5-membered heteroaromatics (indoles, pyrroles, furans, and benzofurans): 08H(76)909. Development and application of effective protocols for the synthesis of arylheteroarenes and biheteroaryls, including bioactive derivatives, by highly regioselective transition metal-catalyzed direct intermolecular arylation reactions of five-membered heteroarenes with (hetero)aryl halides 08COC774. Heteropentalene mesomeric betaines of type C: 08H(75)1.
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Recent progress in the generation and use of nitrogen-centered radicals, particularly, in syntheses of pyrrole, benzothiazole, imidazole, indolizidine derivatives and lactams: 08CSR1603. Ruthenium-catalyzed furan- and pyrrole-ring formation: 08COS343.
5.2. One Heteroatom We have classified many reviews dealing with these materials under the following headings: 1. G eneral. 2. O ne Nitrogen Atom (it is self-subdivided into Monocyclic Pyrroles, Hydropyrroles, Porphyrins and Related Systems, Indoles, Carbazoles, Related Systems, and Hydrogenates Derivatives, Isoindoles Including Phthalocyanins and Porphyrazines, Polycyclic Systems Including Two Heterocycles). 3. O ne Oxygen Atom (Furans, Hydrofurans, Annulated Furans, FiveMembered Lactones). 4. O ne Sulfur Atom (Thiophenes, Annulated Thiophenes). 5.2.1. General Creative approaches toward the synthesis of 2,5-dihydrofurans, -thiophenes, and -pyrroles: 09OBC1761. Preparation of five-membered rings via the translocation–cyclization of vinyl radicals: 08SL2389. New variation of the aromatic ortho-Claisen rearrangement: Synthesis of fused thiophenes and pyrroles: 08SL2400. Synthesis, reactivity, and electronic structure of five-membered heteroaryl and heteroaroyl azides: 09ARK(1)97. 5.2.2. One Nitrogen Atom Phthalocyanine, porphyrin, cyclodextrin, and polymer systems suitable for studying by circular dichroism, magnetic circular dichroism, and/or electrochemistry: 09BCJ631. 5.2.2.1. Monocyclic pyrroles
Barton–Zard pyrrole synthesis and its application to the synthesis of porphyrins, polypyrroles, and dipyrromethene dyes: 08H(75)243. Dimerization of guanidiniocarbonylpyrrolecarboxylate zwitterion as an example of self-assembling in polar solvents based on specific interactions: 08CC801.
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A decade journey in the chemistry of sandwich-type tetrapyrrolato–rare earth complexes: 09ACR79. Synthesis of trifluoromethyl pyrroles and their benzo analogues: 09S3905. 5.2.2.2. Hydropyrroles
Advances in asymmetric reduction of prochiral ketones catalyzed by diphenylprolinol and its derivatives: 09CJO1325. Amide-based bifunctional organocatalysts (mainly, prolinamide analogs) in asymmetric reactions: 09CC6145. Development of a new production process for N-vinyl-2-pyrrolidone: 08BCJ449. Development of organocatalysis based on the molecular design of pyrrolidine Brønsted acid catalysts: 08YGK774. α,α-Diarylprolinols as bifunctional organocatalysts for asymmetric synthesis: 09CC1452. C2-Symmetric pyrrolidines derived from tartaric acids as versatile chiral building blocks for total synthesis, catalyst design, supramolecular and medicinal chemistry: 09COS38. Novel pyrrolidine and pyrroline fullerene derivatives (from their synthesis to the use in light-performing systems): 08IZV873. Organocatalytic asymmetric synthesis using proline and related molecules: 08H(75)493; 08H(75)757. Organocatalytic reactions in water (proline derivatives and cyclic amines as catalysts): 09CC6687. Stereoselective synthesis of quaternary proline analogues: 08EJO3427. Supported proline and proline derivatives as recyclable organocatalysts: 08CSR1666. Synthesis and reactions of 3-pyrrolidinones: 08JHC1549. 5.2.2.3. Porphyrins and related systems
Acid–base properties of porphyrins in nonaqueous solvents: 09MG130. Aza-deficient porphyrin (butadieneporphyrin) as a ligand: 09CCR2036. Boron complexes of porphyrins and related polypyrrole ligands: 08CC2090. Bromination of porphyrins: 09KGS323. Chlorophyll catabolites—Chemical and structural footprints of a fascinating biological phenomenon: 09EJO21. Cobalamins uncovered by modern electronic structure calculations: 09CCR769.
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π-Conjugation enlargement toward the creation of multiporphyrinic systems with large two-photon absorption properties: 09CAJ1172. Corrole: The little big porphyrinoid: 08SL2215. Dendrimer porphyrins: 09CRV6047. Design of porphyrin nanoclusters toward discovery of novel properties and functions: 09BCJ11. Distinctive structural, spectroscopic, photophysical properties and chemical reactivities of corroles: 09CEJ8382. Ferrocene-appended porphyrins: Syntheses and properties: 09CCR21. β-Fluorinated porphyrins and related compounds: 08EJO417. FTIR and optical spectroscopic studies of the reactions of heme models with nitric oxide and other NOx in porous layered solids: 08CCR1486. Iron complexes of octaphenyltetraazaporphyrin: 09MG114. Metal-catalyzed reactions in porphyrin synthesis: 09CC1011. π-Metal complexes of tetrapyrrolic systems. A novel coordination mode in “porphyrin-like” chemistry: 09CSR2716. Metalation of carbaporphyrinoid systems: 08MG9. Metalloporphyrin-based oxidation systems: from biomimetic reactions to application in organic synthesis: 09CC3996. Metalloporphyrins and phthalocyanines as efficient Lewis acid catalysts with a unique reaction field: 09YGK595. Methods for the synthesis of rare-earth element complexes with tetrapyrrole ligands: 08UK938. Modulating the electronic properties of porphyrinoids: 08OBC1877. Organic semiconductors based on benzoporphyrins with thermally or photochemically removable groups: 08CC2957. The photophysical properties of expanded porphyrins: relationships between aromaticity, molecular geometry and nonlinear optical properties: 09CC261. Porphycenes: synthesis and derivatives: 08CSR215. Porphyrin derivatives with carbon–metal bonds: 09YGK688. Porphyrin preparation utilizing sulfonated ionic liquid and control of cation–anion interaction in ionic liquids: 09YGK833. Probing molecular chirality by CD-sensitive dimeric metalloporphyrin hosts: 09CC5958. Progress in binding affinities of metal porphyrins to heterocycles and DNA: 09CJO1700. Progress in µ-oxo-bismetallotetraphenylporphyrin compounds as biomimetic catalysts: 08CJO1685. Progress in the synthesis and application of porphyrin–perylene arrays: 09CJO1906.
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Progress in the synthesis of porphyrins bearing fused rings: 08CJO2039. Reactivity of solvatocomplexes of transition metals in porphyrins coordination: 09MG92. Recent progress in subporphyrins: 09CJO1750. Self-assembled porphyrin nanostructures: 09CC7261. Self-organized porphyrinic materials: 09CRV1630. Self-organized systems based on porphyrins: 08UK60. Structural diversity in expanded porphyrins (penta- to decapyrrolic macrocycles): 08ACR265. Studies on the structure and function of phytochromes as photoreceptors based on synthetic organic chemistry (synthesis of linear tetrapyrrole chromophores of phytochromes as photoreceptors): 08BCJ25. Supramolecular chemistry of metalloporphyrins: 09CRV1659. Synthesis and applications of porphyrins with peripheral metal–carbon bonds: 08AG(E)7396. Synthesis and properties of meso-aryl-substituted tetrabenzoporphyrins: 08IZV1565. Synthesis of molecular synthons for porphyrin-grafted polymers:09MG139. A versatile bisporphyrinoid motif for supramolecular chirogenesis: 09EJO189. 5.2.2.4. I ndoles, carbazoles, related systems, and hydrogenated derivatives
3-Acetylindoles: Synthesis, reactions and biological activities: 09COC1475. Advances on N-arylation of indoles by cross-coupling reactions: 09MRO367. Asymmetric synthesis of axially chiral compounds (particularly, Narylindoles) utilizing planar chiral transition metal complexes and their development for dynamic complexes: 08YGK953. Catalytic functionalization of indoles, 2005–2009: 09AG(E)9608. Catalytic synthesis of indoles from alkynes: 08ASC(350)2153. Efficient synthesis of indoles via [3,3]-sigmatropic rearrangement of N-trifluoroacetylenehydrazines and enehydroxylamines: 09H(78)843. Ethynylindoles and their derivatives. Methods for synthesis and chemical transformations: 09KGS643. Evolution of multicomponent anion relay chemistry (ARC): construction of architecturally complex natural and unnatural products, in particular, indole alkaloids: 08CC5883. Fischer triptamine synthesis using synthetic precursors and latent forms of aminobutanal: 08KGS493.
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Imagination and creation: 1-hydroxyindole chemistry and the dream challenge: 08YZ527. New isatin derivatives: 09ZOR1599. Recent advances in the synthesis of indole derivatives through cascade reactions: 09CAJ1036. The role of the indole in important organocatalytic enantioselective Friedel–Crafts alkylation reactions: 09COC1585. Structures of metal complexes involving indole rings and effects of metal–indole interactions: 09CCR479. Synthesis of compounds having cycloalka[b]indole structure: 09ZOR335. Synthetic applications of the Nenitzescu reaction to biologically active 5-hydroxyindoles: 08COC691. Synthetic indole, carbazole, biindole and indolocarbazole-based receptors: applications in anion complexation and sensing: 08CC4525. Transition metal-catalyzed, direct and site-selective N1-, C2- or C3-arylation of the indole nucleus: 09ASC673. 5.2.2.5. Isoindoles (including phthalocyanins and porphyrazines)
Azaphthalocyanines-containing pyrazine rings: synthesis and properties including those important in photodynamic therapy: 08MG21. Dendrimer phthalocyanines: 09CRV6047. Functionalization of phthalocyanines and subphthalocyanines by transition metal-catalyzed reactions: 08SL1. Organic semiconductors based on phthalocyanins with thermally or photochemically removable groups: 08CC2957. Photophysical and optical limiting properties of axially modified phthalocyanines: 09MRO55. Reactivity of porphyrazines in acid–base interaction with bases: 09MG151. A survey of studies on phthalocyanines and porphyrazines having tetrathiafulvalene units: 08CJO1875. Synthesis and physico-chemical investigations of bi- and polynuclear phthalocyanines: 08UK460. Synthesis of novel tetrahetarenoporphyrazines: 09MG103. 5.2.2.6. Polycyclic systems including two heterocycles
Pyrrolo[1,2-b]pyridazines (an update to the 1976 review of Kuhla and Lombardino): 08ARK(1)232. Recent progress in the chemistry and applications of indolocarbazoles: 08T9159.
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5.2.3. One Oxygen Atom 5.2.3.1. Furans
Reactions of oxidation of furans: 09KGS1283. 5.2.3.2. Hydrofurans
New advances in the synthesis of 2(5H)-furanones: 08CJO29. 5.2.3.3. Annulated furans
Efficient synthesis of benzo[b]furans via [3,3]-sigmatropic rearrangement of N-trifluoroacetylenehydrazines and enehydroxylamines: 09H(78)843. Progress in the synthesis of isobenzofuran derivatives: 08CJO1523. Selective synthesis of benzofurans and dihydrobenzofurans via efficient rearrangement as key reaction: 08YZ1139. Synthesis, transformation and spectral properties of 2H-cyclohepta[b] furan-2-ones: 09H(78)1917. 5.2.3.4. Five-membered lactones
New synthetic approaches to α-methylene-γ-butyrolactones: 09AG(E)9426. Recent developments in γ-lactone synthesis: 09MRO345. 5.2.4. One Sulfur Atom 5.2.4.1. Thiophenes
The chemistry of thiophene S-oxides and related compounds: 09ARK(9)96. Molecular design of functional oligothiophenes for multidimensional nanoarchitectures and their applications: 09CRV1141. Organic semiconductors based on oligothiophenes and isothianaphthenes with thermally or photochemically removable groups: 08CC2957. Palladium-catalyzed CH arylation and dehydrogenative homocoupling of thiophenes. Design of advanced organic materials: 08BCJ548. Phosphorylation of thiophenes: 08COC25. 5.2.4.2. Annulated thiophenes
Organic semiconductors based on isothianaphthenes with thermally or photochemically removable groups: 08CC2957. Synthesis of thienothiophene: 08CJO163.
5.3. Two Heteroatoms We have classified many reviews dealing with these materials under the following headings:
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1. G eneral. 2. T wo Nitrogen Atoms (it is self-subdivided into Pyrazoles, Imidazoles, and Annulated Imidazoles). 3. O ne Nitrogen and One Oxygen Atom (1,2-Heterocycles, 1,3-Heterocycles). 4. O ne Nitrogen and One Sulfur Atom. 5. T wo Sulfur Atoms. 5.3.1. General Diazenes as powerful and versatile tools in organic synthesis (particularly, diazenecarboxamides as precursors for azoles): 09SL2217. 5.3.2. Two Nitrogen Atoms 5.3.2.1. Pyrazoles
Agostic interactions in alkyl derivatives of sterically hindered tris(pyrazolyl) borate complexes of niobium: 09CCR635. The chemistry of 1,2,3,4,5-pentaphenylcyclopentadienyl hydrotris(indazolyl) borate ruthenium(II) complexes, building blocks for the construction of potential organometallic molecular motors: 08CCR1451. Dinitropyrazoles: 09UK643. Novel access to indazoles based on palladium-catalyzed amination chemistry: 08YZ997. Organometallic complexes as anion hosts (particularly, trispyrazolyl borates): 08CC533. Pyrazol-3-ones. Reactivity of the ring substituents: 08AHC(95)27. Pyrazol-3-ones. Synthesis and applications: 09AHC(98)143. Recent advances in the chemistry of indazoles: 08EJO4073. Recent advances in the synthesis of pyrazoles: 09OPP253. Recent developments in aminopyrazole chemistry: 09ARK(1)198. Synthesis and biological activity of pyrazolo[1,5-a][1,3,5]triazines(5aza-9-deazapurines): 08H(75)1575. Synthesis of 4-iodopyrazoles: 08MRO331. Synthesis of trifluoromethylpyrazole derivatives by reactions of hydrazines with trifluoromethyl-β-diketones: 08H(75)2893. 5.3.2.2. Imidazoles
C4-Bound imidazolylidenes: from curiosities to high-impact carbene ligands: 08CC3601. Synthetic routes toward 2-substituted 2-imidazolines: 09T2387.
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5.3.2.3. Annulated imidazoles
Coordination behavior of benzimidazole, 2-substituted benzimidazoles and benzothiazoles, toward transition metal ions: 08ARK(5)245. Progress in the synthesis and application of benzimidazoles and their derivatives: 08CJO210. Research progress in the synthesis of benzimidazoles: 08CJO542. 5.3.3. One Nitrogen and One Oxygen Atom 5.3.3.1. 1,2-Heterocycles
Synthesis and 13C, 17O, 15N, 19F NMR spectroscopy of 5-halomethyl-5hydroxy-4,5-dihydroisoxazoles: 08MRO53. 5.3.3.2. 1,3-Heterocycles
Advances in the synthesis of 2-imidazolines and their applications in homogeneous catalysis: 09ASC489. Bonding capabilities of imidazol-2-ylidene ligands in group-10 transition-metal chemistry: 09CCR678. Camphor-derived α,β-unsaturated oxazolines and oxazoline N-oxides in asymmetric cycloadditions and rearrangements: 09SL3065. Cross-coupling reaction of oxazoles: 08MRO77. Development of planar chiral diarylphosphino-oxazoline ligands and their applications to asymmetric catalysis: 09CJO1487. Interannularly cyclopalladated ferrocenyloxazolines: 05SL1863. Metal-bis(oxazoline) complexes: From coordination chemistry to asymmetric catalysis: 08CCR702. Oxazolo[3,2-a]pyridinium and oxazolo[3,2-a]pyrimidinium salts in organic synthesis. 08IZV831. Peculiarities of chemical properties of imidazole-derived and other types of cyclic nitrones and their use in organic synthesis: 09ARK(4)136. Recent advances in the immobilization of chiral catalysts containing bis(oxazolines) and related ligands: 08CCR624. Synthesis of trifluoromethylisoxazole derivatives by reactions of hydroxylamine with trifluoromethyl-β-diketones: 08H(75)2893. 5.3.4. One Nitrogen and One Sulfur Atom Chemistry and biological activities of 1,3-thiazolidin-4-ones: 08MRO336. Overview of the chemistry of 2-thiazolines: 09CRV1371. Palladium-catalyzed CH arylation and dehydrogenative homocoupling of thiazoles. Design of advanced organic materials: 08BCJ548.
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Progress in the chemistry of 4-thiazolidinones: 08JHC939. Progress in the synthesis of thiazolines: 08CJO1358. 5.3.5. Two Sulfur Atoms Advances in study on Langmuir–Blodgett films based on tetrathiafulvalene derivatives: 09CJO197. Advances in synthesis and research of tetrathiafulvalenes containing a halogen substituent: 09CJO858. Advances in tetrathiafulvalene and its derivatives as molecular switches: 09CJO34. One-pot synthesis of 1,2-dithioles from simple organic substrates and S2Cl2: 09ARK(1)129. Tetrathiafulvalene (TTF) derivatives: key building blocks for switchable processes: 09CC2245. Synthesis, coordination chemistry and radical cation salts of tetrathiafulvalene-based group XV (N, P, As, Sb) ligands: 09CCR1398.
5.4. Three Heteroatoms Oximes of five-membered heterocycles with three and four heteroatoms: 08KGS803; 08KGS963. 5.4.1. Three Nitrogen Atoms 5.4.1.1. Monocyclic systems
Dendrimer design using CuI-catalyzed alkyne–azide “click-chemistry” leading to 1,2,3-triazoles: 08CC5267. Fused 1,2,3-triazoles: 08KGS1295. Progress in syntheses of 1,2,3-triazoles: 09CJO13. Synthesis and properties of nitro-1,2,3-triazoles: 08KGS3. 5.4.1.2. Annulated triazoles
The importance of the N-aryl substituent for development of chiral bicyclic triazolium salt organic catalysts: 08CL2. Recent progress in 1,2,4-triazolo[1,5-a]pyrimidine chemistry. 08AHC (95)143. 5.4.2. Two Nitrogen Atoms and One Oxygen Atom Chemistry and the use of 1,2,4-oxadiazoles: 09OBC4337. 2,5-Dihydro-1,3,4-oxadiazoles and bis(heteroatom-substituted)carbenes: 09ACR205. Recent advances in the synthesis of 1,2,4- and 1,3,4-oxadiazoles: 08COC850.
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5.4.3. One Nitrogen Atom and Two Sulfur Atoms One-pot synthesis of 1,2,3-dithiazoles from simple organic substrates and S2Cl2: 09ARK(1)129.
5.5. Four Heteroatoms Oximes of five-membered heterocycles with three and four heteroatoms: 08KGS803; 08KGS963.
6. SIX-MEMBERED RINGS 6.1. General Cu-catalyzed Diels–Alder reactions (including aza-, oxa-, and thia-Diels– Alder reactions): 08CRV5359. Synthesis of aza- and polyazapyrenes: 08KGS1613. Synthesis and properties of azinylferrocenes: 08H(76)39. Synthesis and properties of diaza-, triaza-, and tetraazaphenothiazines and their benzo and dibenzo derivatives: 09JHC355.
6.2. One Heteroatom We have classified many reviews dealing with these materials under the following headings: 1. O ne Nitrogen Atom (it is self-subdivided into Pyridines, Pyridinium Compounds, Ylides, Pyridine N-Oxides, Applications of Pyridines, Bipyridines and Related Systems, Hydropyridines, Biologically Active Pyridines and Hydropyridines, Pyridines Annulated with Carbocycles, Pyridines Annulated with Heterocycles). 2. O ne Oxygen Atom (Pyrans and Hydropyrans, Annulated Pyrans and Pyrylium Salts). 6.2.1. One Nitrogen Atom 6.2.1.1. Pyridines
Advances in the synthesis of 4-aryl- and 4-hetarylpyridines: 08UK1129. Advances in the synthesis of pyridines by transition-metal-catalyzed [2 + 2 + 2] cycloaddition: 08SL2571. Amino acid-containing reduced Schiff bases as the building blocks for metallasupramolecular structures, particularly, derived from N-(2-pyridyl) amino acid ligands: 08CCR1027. Complex formation of N-donor ligands, particularly, of pyridine-based ligands with group 11 monovalent ions: 08CCR1270.
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6.2.1.2. Pyridinium compounds, ylides, pyridine N-oxides
Oxazolo[3,2-a]pyridinium salts in organic synthesis. 08IZV831. 6.2.1.3. Applications of pyridines
Application of pyridinium salts to organic syntheses: 08CJO1899. Metal–organic cooperative catalysis in C–H and C–C bond activation and its concurrent recovery.Wilkinson’s catalyst (Ph3P)3RhCl–organic catalyst (2-amino-3-picoline) system: 08ACR222. Progress in chiral 4-dimethylaminopyridine derivatives as novel nucleophilic catalysts: 08CJO574. Supramolecular control of reactivity in the solid state: From templates to ladderanes to metal–organic frameworks (pyridyl groups as hydrogen bond donors): 08ACR280. 6.2.1.4. Bipyridines and related systems
Advances in the synthesis of terpyridine ligand and its derivatives: 09CJO504. Analogues of organometallic complexes of polypyridine ligands and N,O(S)-chelating pyridines: 09AHC(98)225. Assemblies, structural diversity, and properties of angular dipyridyl ligands 2,5-bis(4-pyridyl)-1,3,4-oxadiazole and its 3-pyridyl analogue as building blocks for coordination architectures: 09BCJ539. Coordination chemistry of 1,3-di(2-pyridyl)benzene and luminescent properties of its metal complexes: 09CSR1783. Coordination properties of polyamine-macrocycles containing terpyridine units: 08CCR1052. Expanded ligands, mainly, based on 2,2′:6′,2″-terpyridine (tpy)—An assembly principle for supramolecular chemistry: 08CCR842. Interaction and reactivity with biomolecules of platinum terpyridine complexes: 09CCR1495. Iridium terpyridine complexes as functional assembling units in arrays for the conversion of light energy: 08ACR857. Organometallic chemistry of polypyridine ligands: 08AHC(95)221; 09AHC(97)45. Recent developments in the d-block metallo-supramolecular chemistry of polypyridyls: 08CCR940. Square-planar Pd(II), Pt(II), and Au(III) terpyridine complexes. Their syntheses, physical properties, supramolecular constructs, and biomedical activities: 08CRV1834.
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Synthesis and catalytic applications of transition metal PNP and PCP pincer complexes based on aminophosphines, particularly, those with 2,6-diaminopyridine, bipyridines or terpyridines as pincer ligands: 08ACR201. Synthesis, structure and reactivity of platinum terpyridine complexes: 09CCR449. Versatile tools in the construction of substituted 2,2-bipyridines–crosscoupling reactions with tin, zinc and boron compounds: 08CSR2782. 6.2.1.5. Hydropyridines
Applications of TEMPO (2,2,6,6-tetramethylpiperidine-1-oxyl) in synthesis: 08S1979. Chiral bispidines (modified 3,7-diazabicyclo[3.3.1]nonanes): 08S2841. 6.2.1.6. Biologically active pyridines and hydropyridines
A convenient access to the piperidine ring by cyclization of allylsilyl-substituted N-acyliminium and iminium ions as a route to the synthesis of piperidine alkaloids: 08MRO193. Progress in the synthesis and application of nipecotic (piperidine-3-carboxylic) acid and its derivatives: 09CJO1068. 6.2.1.7. Pyridines annulated with carbocycles
8-Hydroxyquinolines in metallosupramolecular chemistry: 08CCR812. 1,10-Phenanthrolines as versatile building blocks for luminescent molecules, materials and metal complexes: 09CSR1690. Progress in catalyst systems for the Friedländer reaction: 09CJO1. Recent advances in the Friedländer reaction: 09CRV2652. Recent advances in the synthesis of quinoline derivatives through cascade reactions: 09CAJ1036. Syntheses, modification, and biological activity of 4-quinolones: 09KGS963. Synthesis and chemical properties of 4-amido- and 4-aminoquinolines: 09IVUZ(10)3. Synthesis and properties of 3-aminodihydroquinolines: 09UK558. Synthesis of substituted 1,2,3,4-tetrahydroquinolines using the Povarov reaction: 08UK138. 6.2.1.8. Pyridines annulated with heterocycles
Advances in the synthesis of imidazopyridine derivatives: 09CJO1708.
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Aromatic γ-carbolynes, their syntheses, chemical and biological properties: 09KGS1123. Methods for cinnolines synthesis: 08KGS643. Synthesis of linear azolo- and pyridoquinolines from quinoline derivatives: 08MRO295. 6.2.2. One Oxygen Atom
6.2.2.1. Pyrans and hydropyrans
Natural and synthetic 2H-pyran-2-ones and their versatility in organic synthesis: 09T7865. Ring transformations of 2H-pyran-2-ones and fused pyran-2-ones with nucleophilic reagents: 09H(77)657. 6.2.2.2. Annulated pyrans and pyrilium salts
Asymmetric synthesis of chiral chromans: 09T3931. Chemistry and application of 4-oxo-4H-1-benzopyran-3-carboxaldehyde: 08JHC1529. Physiological activities and research advance in the synthesis of flavonoids: 08CJO1534. Progress in the study of rotenone derivatives (isoflavonoids): 08CJO1849. Progress in the synthesis of isobenzopyran derivatives: 08CJO1523. Syntheses of chromenes and chromanes via o-quinone methide intermediates: 09JHC1080. Synthesis of chroman-2-ones by reduction of coumarins: 09S3533. Synthesis of prenylated xanthones: 09COC1215. Synthetic approaches to 3H-naphtho[2,1-b]pyrans and 2,3-dihydro1H-naphtho[2,1-b]pyrans: 09JHC1098.
6.3. Two Heteroatoms We have classified many reviews dealing with these materials under the following headings: 1. T wo Nitrogen Atoms (it is self-subdivided into 1,2-Heterocycles, 1,3-Heterocycles, Monocyclic Pyrimidines and Hydropyrimidines Except Pyrimidine Nucleoside Bases and Nucleosides, Annulated Pyrimidines Except Purines, Pteridines, and Flavins, Pyrimidine Nucleoside Bases and Purines, Nucleotides and Nucleosides, Nucleic Acids, Pyrazines and Hydropyrazines). 2. O ne Nitrogen and One Oxygen Atom. 3. O ne Nitrogen and One Sulfur Atom.
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6.3.1. Two Nitrogen Atoms Functionalization of diazines and benzo derivatives through deprotonated intermediates: 08CSR595. 6.3.1.1. 1,2-Heterocycles
Alkyl heteroaromatics (alkylpyridazinyl and alkylcoumarinyl carbonitriles, alkylphthalazines, azolylpyridazines, pyridopyridazines) as precursors to polycyclic heteroaromatics, microwaves as energy source: 08ARK(10)54. Chemistry and applications of 4,5-diazafluorenes: 08H(75)2381. Methods for cinnolines synthesis: 08KGS643. Pyrrolo[1,2-b]pyridazines (an update to the 1976 review of Kuhla and Lombardino): 08ARK(1)232. Recent developments in pyridazine and condensed pyridazine synthesis: 09AHC(97)1. 6.3.1.2. 1 ,3-Heterocycles: monocyclic pyrimidines and hydropyrimidines (except pyrimidine nucleoside bases and nucleosides)
4-Amino-substituted pyrazolo[3,4-d]pyrimidines: Synthesis and biological properties: 09MRO220. New advances in the synthesis of Biginelli 3,4-dihydropyrimidin2(1H)-one derivatives: 09CJO876. New potentialities of the classical Biginelli reaction: 08UK1091. New strategies for the synthesis of pyrimidine derivatives: 08CEJ6836. Recent highlights in the synthesis of highly functionalized pyrimidines: 09OBC2841. Synthesis of pyrimidines and condensed pyrimidines through reactions of nitriles with o-aminocarbonyl substrates under acidic conditions: 09H(78)1627. Transformations of 5-nitropyrimidines: 08JHC621. Uracil as a target for nucleophilic and electrophilic reagents: 08COS365. 6.3.1.3. Annulated pyrimidines (except purines, pteridines, and flavins)
Fluorine-containing quinazolines, their oxa- and thiaanalogues: synthesis and biological activity: 09UK421. Oxazolo[3,2-a]pyrimidinium salts in organic synthesis. 08IZV831. Recent progress in 1,2,4-triazolo[1,5-a]pyrimidine chemistry. 08AHC (95)143.
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6.3.1.4. Pyrimidine nucleoside bases and purines
N-Alkylated guanine derivatives (mainly, 2003–2009): 09COC1085. Application of protecting groups in the synthesis of purine derivatives: 09KGS3. Carbohydrate hydrazones and osazones as organic raw materials for nucleosides and heterocycles: 09COC976. Design and synthesis of 2′-functionalized oligonucleotides. Their application for covalent trapping the protein–DNA complexes: 09COC1029. Interligand interactions involved in the molecular recognition between copper(II) complexes and adenine or related purines: 08CCR1241. Intrinsically fluorescent base-discriminating nucleoside analogs: 09MRO378. Mechanistic aspects of thermal N-9′ → N-7′ isomerization of (6′-substituted)-9-(2,3-dihydro-5H-1,4-benzodioxepin-3-yl)-9H-purines in solution: 08MRO128. Recent advances in the synthesis of purine derivatives and their precursors: 08T8585. Unconventional activators in the synthesis of oligonucleotides and their structural analogues: 09H(79)265. 6.3.1.5. Nucleotides and nucleosides
Cu(I)-catalyzed Huisgen azide–alkyne 1,3-dipolar cycloaddition reaction in nucleoside, nucleotide, and oligonucleotide chemistry: 09CRV4207. Chemical strategies for oligonucleotide-conjugates synthesis: 08COC263. From sugars to modified nucleosides: 09ARK(9)122. Multinuclear NMR studies of the interaction of metal ions with adenine nucleotides: 08CCR2362. Nucleoside-, nucleotide- and oligonucleotide-based amphiphiles: 08OBC1324. C-Nucleosides:Synthetic strategies and biological applications:09CRV6729. Progress in the synthesis of carbocyclic nucleosides: 08CJO1888. Progress in palladium-catalyzed synthesis of pyrimidine nucleoside derivatives: 09CJO44. Recognition of mismatched base pairs in DNA: 09BCJ1055. Xanthosine 5′-monophosphate. Acid–base and metal ion-binding properties of a chameleon-like nucleotide: 09CSR2465. Solid-phase synthesis of base-sensitive oligonucleotides: 09ARK(3)54. The supramolecular organization of guanosine derivatives: 08MRO262. Synthesis of cyclonucleosides having a C–C bridge: 08T7453.
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Synthetic nucleoside chemistry based on nucleoside natural products synthesis: 08CPB1059. 6.3.1.6. Nucleic acids
Catalytic DNA (deoxyribozymes) for synthetic applications—current abilities and future prospects: 08CC3467. Construction and applications of base-functionalized nucleic acids obtained via cross-coupling reactions of nucleoside triphosphates followed by polymerase incorporation: 08OBC2233. Design and synthesis of DNA G-quadruplex ligands: 08OBC627; 09EJO2225. DNA oxidation by active oxygen: 09UK714. Electron, hydrogen atom, proton, and hydride transfers as causes of lesions in DNA subunits: 09ACR563. Electron transfer in DNA and in DNA-related biological processes. Electrochemical insights: 08CRV2622. Interstrand DNA cross-links induced by α,β-unsaturated aldehydes derived from lipid peroxidation and environmental sources: 08ACR793. Mechanistic aspects of the interaction of intercalating metal complexes with nucleic acids: 08CCR1163. Medicinal chemistry targeting nucleosides and nucleic acids based on fine synthetic chemistry: 08YZ1403. A nonheme iron-mediated chemical demethylation in DNA and RNA: 09ACR519. Nucleic acid encoding to program self-assembly in chemical biology: 08CSR1330. Optical detection of DNA and proteins with cationic polythiophenes: 08ACR168. Oxidatively generated damage to the guanine moiety of DNA: Mechanistic aspects and formation in cells: 08ACR1075. 8-Oxoguanine reparation in DNA and mechanisms of enzymatic catalysis: 08UK817. Photochemistry of 5-bromouracil- or 5-iodouracil-containing DNA: Probe for DNA structure and charge transfer along DNA: 09YGK1261. Postsynthetic DNA modification through the copper-catalyzed azide– alkyne cycloaddition reaction: 08AG(E)8350. A role for water molecules in DNA—ligand minor groove recognition: 09ACR11. Synthesis and use of osmium-DNA complexes: 09YGK680.
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6.3.1.7. 1,4-Heterocycles: pyrazines and hydropyrazines
Metallosupramolecular silver(I) assemblies based on pyrazine and related ligands: 08CCR990. Synthetic chemistry with N-acyliminium ions derived from piperazine2,5-diones and related compounds: 09COS143. 6.3.2. One Nitrogen and One Oxygen Atom Chemistry of ring-fused oxazine-2,4-diones: 09EJO3487. 6.3.3. One Nitrogen and One Sulfur Atom One-pot synthesis of 1,4-thiazines from simple organic substrates and S2Cl2: 09ARK(1)129.
6.4. Three Heteroatoms Oximes of six-membered heterocycles with two and three heteroatoms. Synthesis and structure: 09KGS1767. 6.4.1. Three Nitrogen Atoms Synthesis and biological activity of pyrazolo[1,5-a][1,3,5]triazines(5-aza-9deazapurines): 08H(75)1575. The use of ring-opening reactions of 1,3,5-triazines in organic synthesis: 09KGS167.
6.5. Four Heteroatoms “Green” pyrotechnics (tetrazine derivatives): 08AG(E)3330.
7. RINGS WITH MORE THAN SIX MEMBERS 7.1. General Construction of polycyclic natural products by use of transannulation reactions across medium and large rings: 09S691.
7.2. Seven-Membered Rings 7.2.1. One Heteroatom Benzoheteropines with fused pyrrole, furan and thiophene rings: 08AHC(96)1. 3-Methyl-2,5-dihydro-1-benzoxepins and 3-methyl-2,5-dihydrooxepins: 09H(79)243. Synthesis and chemical transformations of benzoxazepines: 08H(75)2155.
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Synthesis of polycaprolactone: 09CSR3484. Synthetic approaches to spiroaminals (1-oxa-7-azaspiro[5.5]undecane, 1-oxa-6-azaspiro[4.5]decane, 1-oxa-7-azaspiro[5.4]decane and 1-oxa-6azaspiro[4.4]nonane ring systems): 08EJO4391. 7.2.2. Two Heteroatoms Synthesis of optically active 1,5-benzothiazepines: 08ARK(1)65. Mechanistic aspects of thermal N-9′ → N-7′ isomerization of (6′-substituted)-9-(2,3-dihydro-5H-1,4-benzodioxepin-3-yl)-9H-purines in solution: 08MRO128. 7.2.3. Three and More Heteroatoms One-pot synthesis of 1,2,3,4,5-pentathiepins from simple organic substrates and S2Cl2: 09ARK(1)129. Synthetic methods for the preparation of triazepandiones and review of their applications: 08COC813.
7.3. Medium Rings [8 + 2] Cycloaddition reactions in synthesis of medium-sized ring systems: 08SL301. New synthetic strategies for medium-sized compounds by palladiumcatalyzed cyclization: 09COC731. One-pot synthesis of 1,2,3,4,5,6,7-heptathiocanes from simple organic substrates and S2Cl2: 09ARK(1)129. Synthesis of heteroannulated azocine derivatives: 08AHC(96)81. Synthetic strategies toward N-functionalized cyclens (1,4,7,10tetraazadodecanes): 08EJO4847.
7.4. Large Rings 7.4.1. General Problems
7.4.1.1. Structure, stereochemistry, reactivity, design
Active metal template synthesis of rotaxanes, catenanes and molecular shuttles: 09CSR1530. Catenanes and threaded systems: from solution to surfaces: 09CSR1674. Light powered molecular machines, mainly, rotaxane-based: 09CSR1542. A macrocyclic approach to transition metal and uranyl Pacman complexes: 09CC3154. Multiple multicomponent macrocyclizations as a strategic development toward macrocycle diversity: 09CRV796.
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Photochemistry of nitrogen-bridged cyclophanes: 2,11-Diaza[32] anthracenoparacyclophane and 2,11-diaza[32]paracyclophane systems: 08SL1931. Polycatenanes: 09CRV6024. Selectivity in supramolecular host–guest complexes (formed by macroheterocycles): 08CSR263. Sulfate anion templation of macrocycles, capsules, interpenetrated and interlocked structures: 09CSR1701. 7.4.1.2. Synthesis
Design and synthesis of porphyrin-containing catenanes and rotaxanes: 09CSR422. Discovery and early development of squaraine rotaxanes: 09CC6329. Evolution of multicomponent ARC for construction of architecturally complex natural and unnatural products, in particular, macrolactones: 08CC5883. Ruthenium-based light-driven molecular machine prototypes: synthesis and properties, particularly, of ruthenium(II) complexed rotaxanes and catenanes: 08CSR1207. 7.4.1.3. Applications
Molecular constructor for light-sensitive and light-emitting nanosystems based on unsaturated and macrocyclic compounds (crown compounds and cucurbiturils): 08IZV1299. Organic chemosensors with crown groups: 08KGS1123. 7.4.2. Crown Ethers and Related Compounds Chemosensors with crown ether-based receptors: 08ARK(4)90. Design of optical molecular sensors and photo-controllable receptors based on crown ethers: 08UK39. Synthesis of N-pivot lariat ethers (aza crowns with N-substituents): 08JHC1. Synthesis of C-pivot lariat ethers: 09JHC1035. Unusual supramolecular donor–acceptor complexes of bis(crown)stilbenes and bis(crown)azobenzene with viologen analogs: 08IZV779. 7.4.3. Miscellaneous Macroheterocycles Chemistry of azacalixarenes: 09YGK898. Chiral macrocyclic Schiff bases: 08MRO228.
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Complex systems (particularly, catenanes and macrocycles) from simple building blocks via subcomponent self-assembly: 08SL3077. Conjugates of calixarenes and heterocycles in the design of newer chemical entities: 09AHC(97)219. Cryptophanes and their complexes: 09CRV88. Cucurbit[n]urils: from mechanism to structure and recognition function: 09CC619. Heterocalixaromatics, new generation macrocyclic host molecules in supramolecular chemistry: 08CC4541. Interlocked host rotaxane and catenane structures for sensing charged guest species via optical and electrochemical methodologies: 09OBC415. Marchantiophyta (liverworts) as rich sources of macrocyclic bis(bibenzyls): 08H(76)99. New synthetic development of cucurbit[n]uril derivatives and analogues: 09YGK1282. New synthetic strategies for macrocyclic compounds by palladium-catalyzed cyclization: 09COC731. Oxacalix[n](het)arenes: 08CSR2393. Receptors for anions (particularly, N-heterocycles, calix[4]pyrroles, porphyrins, criptands and cyclic peptides as receptors): 08UK803. Rotaxanes of a quaternary azaaromatic character: 09COC339. Strapped and other topographically nonplanar calixpyrrole analogues. Improved anion receptors: 08CC24. Structure, synthesis and application of calixpyrrole and heterocalixpyrrole: 08CJO398. Surfactant-type catalysts (particularly, calix[n]arenes bearing sulfonic acids and imidazolium salts) in organic reactions: 09T587. Synthesis and applications of chiral perazamacrocycles: 09COS102; 09COS119.
8. HETEROCYCLES CONTAINING UNUSUAL HETEROATOMS 8.1. Phosphorus Heterocycles 8.1.1. Chemistry of Individual Classes of P-Heterocycles Aromaticity and antiaromaticity of four-membered P-heterocycles: 08COC83. Stabilized phosphazides including cyclic phosphazides: 09CCR1248.
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Synthesis and coordination chemistry of phosphole-containing calixpyrroles, calixphyrins, and porphyrins: 09ACR1193. 8.1.2. Structure and Stereochemistry Cyclophosphazene-based ligands for the assembly of multimetal architectures: 09ACR1047. 8.1.3. Synthesis Design and synthesis of phosphole-based π-systems for novel organic materials: 09OBC1258. Diels–Alder reactions involving C = P functionality, particularly, including transformation and/or preparation of P-heterocycles: 08T10945. Recent perspectives on main group-mediated dehydrocoupling of P–P bonds, particularly, leading to formation of heterocycles with two phosphorus atoms: 09CC4929.
8.2. Boron Heterocycles 8.2.1. Chemistry of Individual Classes of B-Heterocycles Recent developments in the chemistry of 1,3,2-diazaborolines-(2,3-dihydro-1H-1,3,2-diazaboroles): 08CCR1. Some aspects of chemical behavior of icosahedral carboranes: 08IZV801. 8.2.2. Synthesis Synthesis of diamond-like structures based on allylboranes: 08IZV788. 8.2.3. Applications Design and synthesis of boron-containing functional π-electron materials, mostly, B-heterocycles: 08YGK858. Enantioselective catalysis based on cationic oxazaborolidines: 09AG(E)2100.
8.3. Silicon, Germanium, Tin, and Lead heterocycles 8.3.1. Chemistry of Individual Classes of Heterocycles Nickel-catalyzed reactions with trialkylboranes and silacyclobutanes: 08CC3234. Singly bonded catenated germanes: Eighty years of progress: 08CRV4253. Substituent effects on the electronic structure of siloles: 09CC1948. Synthesis and reactivity of four-membered silacycles: 09CJO491.
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8.3.2. Synthesis Cyclic siloxanes as intermediates in precision design of structure and function of silicon-containing oligomers and polymers: 08YGK148.
8.4. Selenium and Tellurium Heterocycles 8.4.1. General Sources and Topics Recent advances in organoselenium chemistry (syntheses of seleniumcontaining heterocycles, such as 3-selena-1-dethiacephems, selenazepines, 1,3-benzoselenazoles, 4′-selenonucleosides, and unsaturated selenacrown ethers, as well as carbonylation of haloselenophenes): 09EJO1649. 8.4.2. Chemistry of Individual Classes of Heterocycles Chemistry of 1-benzotelluropyrylium salts: 09YGK714. Chemistry of selena macrocycles: 09CCR1056. Developments in tellurium-containing macrocycles: 09CCR1947.
8.5. Other Unusual Heterocycles Chemistry of polyvalent iodine (benziodoazoles and benziodooxoles, hypervalent iodides in the synthesis of heterocycles, iodine(V) heterocycles): 08CRV5299. 8.5.1. Metallacycles Enantioselective cross-coupling of anhydrides with organozinc reagents: The controlled formation of carbon–carbon bonds through the nucleophilic interception of metalacycles: 08ACR327. Heterocycle formation from zirconacycles: 08H(76)923. Metallacalixarenes: organo-inorganic hybrid molecular architectures: 08AHC(96)123. On inventing catalytic reactions via ruthena- or rhodacyclic intermediates for atom economy: 08SL629. 8.5.2. Metal Chelates and Related Complexes Group 9 metal complex-catalyzed hydrogen transfer reactions and their application to organic synthesis, particularly, to hydrogenation of nitrogen heteroaromatics and formation of N-heterocycles: 08YGK322. Hetarylazomethine metal complexes: 09AHC(97)291. Trinuclear metallacycles: Metallatriangles and much more: 08CRV4979.
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