GRAPHICAL ABSTRACTS
r~r~~orr~-s~ ~ ~
I Tetrahedron, 1997, 53, 13221
rsxrl:coNsravcnoNoFa'mtcl~c~vnAGrcmrcr
K Irehmd,*LengbinLiu,§and Theem D. Rel~ of Cnenmy, Univenityef Vklliaia
"
ODPSO~
o
"
Me
"
"'-
PO
rO'r,.,Lsvm'nv~mov~-sa~ Purr z:c o ~ o N
I
[ Tetrahedron,1997, 53, 13257
OF'ThESVSTnr,SIS
RobertE. lrelm~l,*LongbinLiu,§ThomasD. Roper,and JemcsL. Gleason Del~tmmt°fChemimy'Vmv~ity°fVirginia
HO~,~
Met" v
-~
~
.Me .....
Me
I Tetrahedron, 1997, 53, 13285 A Theoretical Study of Acetylene, Ethylene, and Cyclopropene Additions to Benzo[b]- and Benzo[c]-fused Heterocycles Branko S. Jursic, Department of Chemistry, University of New Orleans, New Orleans, Louisiana 70148 The AM1 and B3LYP/6-31G(d) theoretical methods have been employed to investigate the reactivity of benzo-heterocycles.Three qualitativecriteria were used to assess their reactivityin Diels-Alder reactions: bond orders, frontier molecular orbitals, and molecular orbital uniformity.
~
Synthesis of $',ll-Dihydroxy-AS-tetrahydrocannabinol
~
I [ Tetrahedron, 1997, 53, 13295
J. W. Huffman,* M.-J Wu, W. K. Banner and D. Dai, Department
of Chemistry,ClemsonUniversity,Clemson,SC 29634-1905.
CH20H The synthesisof5',1l-dihydroxy-A8-tetrahydroeannabinolhasbeen carriedout. Thispolaremmabinoidhasconsiderablylessaffinityfor the cannabinoidbrainreceptorthanA8-THC.
H
H3
OH OH OH
Tetrahedron, 1997, 53, 13307 Enantioselective Constractioa of Alieyellc Bicyclo13.1.0]hexnne Framework by Doable Stereodifferentlatioa and its Application for the Synthesis of Both Enaatiomers of Vitamin !)3 CD Ring S y l t h o n s Mingqi He/Shinji Tanimori,*'= Susumu Ohira,b Mitsuru Nakayama' 'Department of@plied 8ioc~mistry, OsakaPrefectureUniversity,1-1 Gakaen-cho,Sakai, Osaka593, Japan bDepartraentof Biological Chemistry,Facultyof Science, Okayama Universityof Science, 1-1 Ridai-cho, Okayama 700, Japan o
0
o
10 mol% N. N~.t~ RO an" cu" ~Bn OTf ~ C~-I~ reflux, 20 h, 53%
O V'ffamin D3CD Ring Synthon
700 de
Tetrahedron, 1997, 53, 13315 SYNTHESIS OF 4'-C-FLUOROMETHYLNUCLEOSlDES AS POTENTIAL ANTINEOPLASTIC AGENTS Kenji Kitano* and Shinji Miura, BiochemicalsDivision, Yamasa Corporation, 2-10-1 Araoieho, Choshi, Chiba 288, Japan. Hiroshi Ohrui and Hiroshi Meguro, Department of Applied Biological Chemistry, Faculty of Agriculture, Tohoku University, 1-1 Tsutsumidori-Amamiya,Aoba-ku, Sendai 981, Japan. BnO-~(,~O~ ~ HO ~ o ~ C Y o o,oc-
-
HO
6:RI=H, R2=OH 7: RI=OH, R2=H
Rz
8 Three4'-C-flooromethylnucleosides5-7 werepreparedfrom D-glucose.
T NEW ALKALOIDS FROM ISA TIS INDIGOTICA L Xiaoyun WuI, Guowei Qin j*, Kung Kai Cheung2 and Kill Fai Cheng~ Shanghai Institute of Materia Medica, Chinese Academy of Sciences, Shanghai 20003 l, China r'-x 2 Department of Chemistry The University ofHong Kong Hong K o n g ~ °:~1"~:": ~'~'~'''' ,n Two new alkaloids isaindigotidione (1) and isaindigotone (2) were isolated from the plant roots. 1 is a novel indolizino[7,6-c]quinolinederivative.
Tetrahedron 1997 53 13323
oc
O ~ N ~
OO ?
~"' % ~"*"N'~o ~-r/"-~
H
1
OC~
oc~
2
REGIOSELECTIVE SYNTHESIS AND PHOTOOXYGENATIONS OF Tetrahedron, 1997, 53, 13329 FURONAPHTHOPYRONES STARTING FROM 2,7-NAPHTHALENEDIOL Zhi-Fu Tao, Xuhoag Qian, and Mingcai Fan Institute of Pesticides and Pharmaceuticals, East China University of Science and Technology " P. O. Box 544, Shanghai 200237, People's Republic of China Three angular furonaphthopyrones 4, 9, 12 were regioseleetivelysynthesizedstarting from H C 2,7-naphthalenedioi in three steps, respectively. An easy separation of Peehmann 3 ~ O condensationpreductsland2of2,7-naphthalenediolwithethylacetuacetatewas H3C~o~o described. The photooxygenationsof 4,12 were investigatedand a hydroperoxide 18 was isolated and fully characterized HaG 12
vi
HaC O ~ = t
~
0 4
CH3
Tetrahedron, 1997, 53,
13339
SYNTHESIS AND ELECTRONIC STRUCTURE OF 1,2-HETEROARYLETHYNES: MONOMERS FOR LOW BANDGAP CONDUCTIVE POLYMERS S. C. Ng'*, I. Novak'*, L. Wang', H. H. Huangj, W. Huang re'b* • Department of Chemistry, National University of Singapore, Singapore 119260 b Department of Chemistry, Peking University, Beijing 100871, China. Br
Y:--'~
ii
~
h Bu3SnOMe, 100 °C, 3hrs; or Bu3SnNEt2,22-25 *C, 17hrs. ii: (MeCN)2PdCI2, DMF, r.t. 10hrs.
Y---a
X = O, S, Se Y = N, C.
I I Tetrahedron, 1997, 2-BROMO-1 -ARYLETHYLIDENEMALONONITRILES CONVENIENT I REAGENTS FOR THE REGIOSELECTIVE SYNTHESIS OF FUSED PYRIDINES Vasilii A.Artyomov*, Vladimir L.lvanov, Anatolii M.Shestopalov, Victor P.Litvinov Cascade reactions of conjugated thiolatonitriles with 2-bromo-1-arylethylidenemalononitrileslead to fused pyridines (thienopyridines,thiazolopyridines, tienodipyridinesand pyridotienopyrimidines) CN
R/~ /CN + S- BH+
~ Br
CN
B ~--
R X~
~ "~.
I Ar
53,
13351
Tetrahedron, 1997, 53,
13361
H2 B=pipendine N X = N. CR
THE ACTIVATION OF AMINALS AND AMINOL ETHERS BY SULFUR DIOXIDE AND THEIR REACTIONS WITH ELECTRON RICH AROMATIC COMPOUNDS H. Heaney, G. Papageorgiou, and R.F. Wilkins Department of Chemistry, Loughborough University, Leicestershire, LEI I 3TU Me
Me
Me NR 2
R2 N
~ Me
SO2
~
Me
NR 2
Me
SO2
Me
Me
DIASTEREOSELECTIVE ADDITION OF ALLYL REAGENTS
Tetrahedron,1997, 53,
13373
TO N-TOSYL- AND N-BENZYL-N-TOSYL-L-ALANINAL Dorota Gryko," Zofla Urba'~czyk-Llpkowska," and Jannsz Jurczak"b* "Institute of Organic Chemistry, Polish Academy of Science~, Kasprzaka 44, 01-224 Warsaw, bDepartment of Chemistry, Warsaw University, 02-093 Warsaw, Poland. Addition of allyl reagents to N-protected L-alaninals leads to the C3-elongationproducts with high diastereoselectivity. RNTs
RNTs
RNTs -
._-
vii
T
Tetrahedron, 1997, 53, 13383
L
SYNTHESIS OF NOVEL QUINAZOLINE-BASED ANTIFOLATES WITH MODIFIED GLUTAMATE SIDE CHAINS AS POTENTIAL INHIBITORS OF THYMIDYLATE
SYNTHASE
AND
ANTITUMOUR
A G E N T S . V a s s i l i o s Bavetsias, 1. G r a h a m M. F. Bisset, 1 Rosemary Kimbell, 1 F. T h o m a s Boyle 2 and A n n L. Jackman 1, linstitute of Cancer Research, CRC Laboratory, Surrey SM2 5NG, UK; 2Zeneca Pharmaceuticals, Cheshire SKI0 4TG, UK The synthesis of novel quinazoline anfifolates with modified glutamate side chains (e. g. 26) is described. 0 ~ F H
^
.COOH ,
COOH
H N ' Y , ~ Y "N--~\ /)'-'--If" .~., ~ _ _N 1 . J~ J.L ~ 6 H "/ ']F-'N H 3C'~'~N""%'~%C Ha 26 N-N ~
Tetrahedron, 1997, 53, 13397
P~RJI~.ATALY~ III~IILI~OANNULATIONWITH A ~ CAllB~IOI~ AS S~Y'II~NS-S~Y'rliI~IS OF QU]gqOLIHqI~ AND 2, 3-D]H[IYDRO4(I I I ) 4 ~ O L O N E S
0
O [ ~
Jyan S Mahanty, Mahuya De, Paias Das and Nltya G Kundu*
-~----~
. R2
Department of Organic Chemistry, Indian Association for the Cultivation of Science, Jadavpur, Calcutta - 700 032, India. + HCmC~C(OH)R2R3 R
NHR1
" q ' " ~ O R 4 Rz
H
/
Pd(O) . R ~ ~ C ( O H ) ~..,,~NHRI
R2R3 NaOEt/EtOH(R1= COCF3) a R or Pd(II) (R1= H)
R2
-r A STUDY ON THE OPEN CHAIN MODEL FOR TRANSITION
Tetrahedron, 1997, 53, 13419
[
STATE STRUCTURES IN THE NUCLEOPHILIC ADDITION TO ~-SUBSTITUTED CARBONYL COMPOUNDS AND ITS APPLICATION TO THE 1,3 ASYMMETRIC INDUCTION
C. Bonini." V. Esposito.J M. D'Auria.' G. Righi ~' a) Dipartimento di Chimica Universild della Basilicata. Via N. Sauro 85. 851l~) Potenza. Italy - b) Centro CNR per Io Studio della
X Hl.~r"l RI3~H
~
~
H.~ ~"f')~
Chinuca. Universit:i di Roma "'La Sapienza". P.I¢ A. Moro 5. 00185 O ~ "R Roma. Italy By means of semi-empiricalquantum-mechanicalcomputations two conformers (C~ and (22) are found to be the most probable as reactant as reactant-like transition state structures, in the general non-chelating nucleophilic C 1 addition to [~-substitutedcarbonyl compounds.
02
Tetrahedron, 1997, 53, 13427
EXPERIMENTAL AND THEORETICAL STUDIES ON THE
DIASTEREOSELECTIVE DIELS-ALDER REACTIONS OF CHIRAL 1-ALKOXY-1,3-BUTADIENES. I: PARENT SYSTEM AND 4-SUBSTITUTED DERIVATIVES
Marina Virgili, Miquel A. Periods*, Albert Moyano*, Antoni Riera URSA, Departament de Quimica Orgb.nica, Universitat de Barcelona. Marti i Franqu~s, 1-11, 08028 Barcelona, Spain. R°O
O
X = CH; Y = O x
R*O - ' -
H
~,,
R . O ~
R
H
Diels-Alder • [~
viii
O
[ Up to 100% yield ] [ Up t° 95 : 5 d'r"
J
I I Tetrahedron, 1997, 53,
INTRAMOLECULAR [2+21CYCLOADDITION OF KETENIMINES
13449
WITH IMINES. SYNTHESIS AND CHEMICAL BEHAVIOUR OF
AZETO[2,1.b]QUINAZOLINES Marco Alajaffn,* Pedro Molina, Angel Vidal and Fulgencio Tovar Departamento de Qufmica Org~nica, Facuitad de Qulmica, Universidad de Murcia, Campus de Espinardo, E-30071, Murcia, Spain. R1 _ t_ ~
The scope and applicability of the intramolecular [2 + 2] cycloaddition reaction of ketenimines with C=N bonds is presented along with the reactivity of the reaction products,
-
R2
Rl
-
t ~
~[~N
n = 1, 2
1 I Tetrahedron,
THE ENE REACTION BETWEEN MALEIMIDES AND ALLYL-
1997,
53,
13473
53,
13495
SUBSTITUTED AROMATICS Ian D. Cunningham,* Andrew Brewnhill, Ian Hamerlon, and Brendan J. Howlin
Departmentof Chemistry, Universityof Surrey, GuildfordGU2 5XH, Uh" The ene reaction of a range of allyl-substituted triazinyl aromatics with maleimide enophiles has been studied o ~ Y = O, NH, NPh, NPhOPh
~Y
x
0
T CATALYSIS WITH INORGANIC CATIONS. VIL 1 THE CATALYTIC [ PROCESS OF THE DIELS-ALDER REACTION WITH MAGNESIUM PERCHLORATE IN CH2CI2: KINETIC INVESTIGATION AND SPECTROSCOPIC DETECTION OF THE COMPLEXED INTERMEDIATE. Giovanni Desimoni, Giuseppe Faita. MarieUa Mella, Marina Ricci, and PierPaolo Righetti. Dipartimento di Chimica Organica dellTlniversit/t, V.le Taramelli 10, 1-27100 Pavia, Italy. RO ~=:=O ~OR ' .'"O~x==~Ar A/ "~=::=0" " O - - ~ O R HA RO 5
HA
r.>=(
Tetrahedron,
1997,
The 2-arilydene-malonic acid dimethyl ester is a dienophile suitable to be coordinated by Mg(II). The formation of the dienophile/eation complex 5 has been demonstrated by NMR spectroscopy, whose reactivity was inferred kinetic methods. The affinity for Mg(lI)of the reacting dienophile allows the reaction to be performed under catalytic conditions, whose steps were clarified by both spectroscopic and kinetic methods.
ix
R2 3 4