- Email: [email protected]
Chemistry of 4-hydroxy-2(1H)-quinolone. Part 2. As synthons in heterocyclic synthesis
Arabian Journal of Chemistry (2014) xxx, xxx–xxx
King Saud University
Arabian Journal of Chemistry www.ksu.edu.sa www.sciencedirect.com
REVIEW
Chemistry of 4-hydroxy-2(1H)-quinolone. Part 2. As synthons in heterocyclic synthesis Moaz M. Abdou
*
Egyptian Petroleum Research Institute, Nasr City, P.O. 11727, Cairo, Egypt Received 2 June 2014; accepted 3 November 2014
KEYWORDS 4-Hydroxy-2(1H)-quinolone; Heterocycles; Microwave irradiation; Ionic liquid; Multicomponent reactions; Electrochemical routes
Abstract This review presents a systematic and comprehensive survey of the utility of 4-hydroxy2(1H)-quinolone as a building block of heterocyclic compounds. The reaction mechanism is considered as well as the scope and limitation of the most important of these approaches are demonstrated. ª 2014 The Author. Production and hosting by Elsevier B.V. on behalf of King Saud University. This is an open access article under the CC BY-NC-ND license (http://creativecommons.org/licenses/by-nc-nd/3.0/).
Contents 1. 2.
3.
Introduction . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . Synthesis of fused heterocyclic compounds . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 2.1. [6-6-5] ring system. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 2.1.1. Dihydrofuran and furoquinolinones . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 2.2. [6-6-5] ring system. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 2.3. Fused [6-6-6] ring system . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 2.3.1. Quinolino[4,3-b]benzo[f]quinolin-6-one . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 2.3.2. Pyranoquinolines . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 2.3.3. Quinolinobenzothiazinones . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 2.4. [6-6-8-6] ring system . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 2.4.1. Oxazocines . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . Conclusion . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
00 00 00 00 00 00 00 00 00 00 00 00
* Tel.: +20 1000409279. E-mail address: [email protected]. Peer review under responsibility of King Saud University.
Production and hosting by Elsevier http://dx.doi.org/10.1016/j.arabjc.2014.11.021 1878-5352 ª 2014 The Author. Production and hosting by Elsevier B.V. on behalf of King Saud University. This is an open access article under the CC BY-NC-ND license (http://creativecommons.org/licenses/by-nc-nd/3.0/). Please cite this article in press as: Abdou, M.M. Chemistry of 4-hydroxy-2(1H)-quinolone. Part 2. As synthons in heterocyclic synthesis. Arabian Journal of Chemistry (2014), http://dx.doi.org/10.1016/j.arabjc.2014.11.021
2
M.M. Abdou Acknowledgements . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 00 References . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 00
1. Introduction 4-Hydroxy-2(1H)-quinolone is a versatile and convenient precursor for the synthesis of a wide variety of heterocyclic compounds (Ghandi et al., 2013; Guo et al., 2013; Abbaspour-Gilandeh et al., 2013; Neve et al., 2014; Hoecker and Gademann, 2013). It is of particular interest as a very promising reagent for cascade heterocyclization, which will undoubtedly become one of the main approaches to the targeted synthesis of heterocycles in the near future, in the rapidly-rising field of combinatorial chemistry. This new methodology based on automatic, high-tech synthetic methods enables synthesis of a large number of novel organic compounds as subjects for biological screening. The first part of this review article (Abdou, 2014) is concerned with the progress in 4-hydroxy-2(1H)-quinolone chemistry and deals with the synthesis, chemical reactivity and reactions of 4-hydroxy-2(1H)-quinolone. This second part systematizes the application of 4-hydroxy-2(1H)-quinolone in heterocyclic synthesis. The enolic reactive center in this compound provides ample opportunities to synthesize a great variety of novel compounds under relatively mild conditions and using simple laboratory equipment. Thus, the two parts are complementary and display current trends in 4-hydroxy2(1H)-quinolone chemistry. In the literature survey, the reactions involving 4-hydroxy2(1H)-quinolone occur with regioselectivity and its course can easily be controlled by changing reaction conditions and varying substituents in the molecules of initial compounds. The heterocyclic compounds are obtained in a single step with high yield and they are reported in order of the increase of (i) the number of rings, (ii) the size of such rings and (iii) the number of heteroatoms present. The sequence of heteroatoms followed is: nitrogen, oxygen and sulfur. The site of fusion in fused heterocycles is indicated by numbers and letters and the numbering of the heterocyclic ring systems is that reported by chemical abstracts.
and furoquinolinones have been well reported (Senboku et al., 1996; Suginome et al., 1990, 1991; Rao and Darbarwar, 1989; Neville et al., 1991; Grundon and Surgenor, 1978). 2.1.1.1. Oxidative cycloaddition reaction mediated by metal salts. The oxidative addition reaction of carbon-centered radicals to alkenes mediated by metal salts Ag(1), Ce(IV) and Mg(II) has received considerable attention over the last decade in organic synthesis for the construction of carbon– carbon bonds. 2.1.1.1.1. Using Ag (1). Lee et al. (2000) have reported that a facile and simple method for the synthesis of dihydrofuran, 2-ethoxy-3,5-dihydro-2H-furo[3,2-c]quinolin-4-one 3, is mediated by the oxidative cyclization of 4-hydroxy-2(1H)-quinolone 1 with ethyl vinyl ether 2 and silver(I)/Celite (Fetizon reagent) in acetonitrile under reflux (Scheme 1). Although the exact mechanism of the reaction is not clear yet, it is best described as shown in Scheme 2. The starting material 1 is first oxidized by one equivalent of Ag(I) to generate the radical 4, which then attacks olefin 2 to give the radical adduct 5. The adduct 5 now undergoes fast oxidation by another one equivalent of Ag(I) to a carbocation 6. Cyclization of the carbocation 6 furnishes intermediate 7, whose deprotonation affords the product 3 (Scheme 2). 2.1.1.1.2. Using Ce(IV). There has been a considerable interest in the use of CAN oxidation reactions in ionic liquids. Hence, reaction of 1 with a-methylstyrene 8 and cerium(IV) ammonium nitrate (CAN) mediated 1-n-butyl-3-methylimidazolium tetrafluoroborate[bmim][BF4]-dichloromethane (1:9), gave tricycles 9,10 (Bar et al., 2003) (Scheme 3). 2.1.1.1.3. Manganese(III) acetate. Mn(III)-based oxidative radical cyclization of 4-hydroxy-2(1H)-quinolone 1 with OEt O
OH + N H 1
OEt
O
Ag2CO3 / Celite acetonitrile/ reflux
N H 3
2
O
2. Synthesis of fused heterocyclic compounds Scheme 1
2.1. [6-6-5] ring system 2.1.1. Dihydrofuran and furoquinolinones Dihydrofuroquinolinone and furoquinolinone alkaloids are widely distributed in nature (Subramanian et al., 1992; Shobana and Shanmugam, 1986; Shobana et al., 1988; Ukrainets et al., 2006). They are primarily isolated from Rutaceae species as an angularly and linearly fused structure. They are reported to have various biological activities such as antimicrobial, antimalarial, insecticidal, antineoplastic, antidiuretic, antiarrhythmic and sedative (Wolters and Eilert, 1981; Svoboda et al., 1966; Basco et al., 1994). This wide range of biological properties has stimulated interest in the synthesis of dihydrofuroquinolinone and furoquinolinone derivatives. A number of synthetic approaches to dihydrofuroquinolinones
O
OH
.
Ag (I) N H
O
N H
Ag (0)
1 + OEt
Ag (I) Ag (0)
2 O
N H
4 O
OEt
O + N H
O
O
5
-H+ N H 6
. OEt
O
3
O
7
Scheme 2
Please cite this article in press as: Abdou, M.M. Chemistry of 4-hydroxy-2(1H)-quinolone. Part 2. As synthons in heterocyclic synthesis. Arabian Journal of Chemistry (2014), http://dx.doi.org/10.1016/j.arabjc.2014.11.021
Chemistry of 4-hydroxy-2(1H)-quinolone
3 Ph
O
OH CAN-[bmim][BF4]
+ N H 1
+
CH2Cl2 / 40o C
O
OH
N
N
OH
Ph
10 (35%)
9 (42%)
8
O
Scheme 3
1,1-diphenylethene 11 in boiling glacial acetic acid afforded 3,5-dihydro-2H-furo[3,2-c]quinolin-4-one 12 (Kumabe and Nishino, 2004) (Scheme 4). Despite the uncertainty related to the reaction mechanism, the authors point toward manganese(III) that could oxidize tertiary carbon radical 14 to afford the corresponding carbocations 15, 16 which were converted into compound 12 (Scheme 5).
Ph Ph
+ N H
Mn(OAc)3 Ph AcOH/100oC
Ph
N H
O
O
12 (73%)
11
1
2.2. [6-6-5] ring system Laccase (Agaricus bisporus)-catalyzed domino reaction of 4hydroxy-2(1H)-quinolone 1 with catechols 20 using aerial oxygen as the oxidant delivers for the synthesis of 10-substituted 8,9-dihydroxybenzofuro[3,2-c]quinolin-6(5H)-ones 21 as single regioisomers with yields ranging from 61% to 77% (Hajdok et al., 2009) (Scheme 7). Some of these compounds have been made accessible by other methods, including tyrosinase-catalyzed oxidation, electrochemical oxidation or crude peroxidase
O
OH
A similar, manganese(III)-mediated reaction using 4hydroxy-2(1H)-quinolone 1 and the alkenes 17 in [bmim] [BF4]–dichloromethane gave a 1:1 mixture of the angular and linear tricycles 18 and 19, respectively (Bar et al., 2001a,b) (Scheme 6).
Scheme 4 R
O
OH
Mn(III) O
Mn(OAc)3 N H
O
OH
Ph . Ph
OH
11
AcOH, reflux
N H
O
N H 14
13
1
Ph
Ph + Ph O Mn(OAc)3 N H 15
-H+
N H
O
O
O
OH 20
Ph
O +
AcOH, reflux
12
O
16
Scheme 5
OH N H 21
O
Yield %
20, 21
R
t/h
a
H
20
73
b
Me
18
77
c
OMe
20
61
Scheme 7
R1 OH
O +
N H 1
cat. laccase, O2 pH=6.0, r.t.
+ N H 1
OH
O
R
O
R2
Mn(OAc)3, 40 C
R1
[bmim][BF4]:CH2Cl2
R2
o
+ N
17
18
17, 18, 19
R1
R2
Yield% (18/19)
a
Ph
H
41/39
b
Me
Ph
41/34
H
71/8
Me
41/4
c d
C 3H 7 C6H 13
OH
OH
N
O
R2 R1
19
Scheme 6
Please cite this article in press as: Abdou, M.M. Chemistry of 4-hydroxy-2(1H)-quinolone. Part 2. As synthons in heterocyclic synthesis. Arabian Journal of Chemistry (2014), http://dx.doi.org/10.1016/j.arabjc.2014.11.021
4
M.M. Abdou OH OH
O
O
oxidation
OH
O
-2e, -2H
20a
N
H N
22
+ _ OH
_
OH O
N H 1
N H 23
22 _ OH
_
O N H 24
N H
OH
1
O
MeO
O
AcOH
O
O
R
N H
O
34
R= OMe, Ph
Scheme 11 OH
O
benzoquinone 22, which then undergoes an intermolecular 1,4-addition with the enol of 1 as a nucleophile to yield 23. A second laccase-catalyzed oxidation to the quinone intermediate (24) which further undergoes an intramolecular 1,4-addition to produce the final tetracyclic heterocycles.
OH
1,4-addition
O
N H 25
O
Scheme 8
2.3. Fused [6-6-6] ring system
from onion solid waste (Pandey et al., 1989; Tabakovic et al., 1983; Angeleska et al., 2013). The reaction is postulated to proceed through a domino process involving several steps (Scheme 8). Initially, the laccase-catalyzed oxidation of the catechol 20 with O2 to
2.3.1. Quinolino[4,3-b]benzo[f]quinolin-6-one A short and simple synthesis of quinolino[4,3-b]benzo[f]quinoline derivatives 27 was accomplished in high yields via the
HN
OH
R TEBAC H2 Ol100 oC
N
+ N H
R
33
O
O
oxidation -2e, -2H
1,4-addition
O
O
OH
H N
O
O
N H
R
27
26
1
O
26, 27
a
b
c
d
e
f
g
h
Ar
2-Cl
4-Cl
3,4-Cl 2
2,4-Cl 2
4-F
4-Br
4-CH 3
3-Cl
Time/ h
8
8
8
8
8
10
12
10
Yield %
94.2
90.2
93.2
97.0
92.5
93.5
91.6
87.8
Scheme 9
OH
OH
Ph
N H 28
O
N
Ph
N H
+ N H 1
O 26
OH
H2 O
NH2
Ph
H2 N O
OH 30 N H
O
N H 31
29
HN
HO HN Ph N H
O
O
-H2O
Ph N H
O
27
32
Scheme 10
Please cite this article in press as: Abdou, M.M. Chemistry of 4-hydroxy-2(1H)-quinolone. Part 2. As synthons in heterocyclic synthesis. Arabian Journal of Chemistry (2014), http://dx.doi.org/10.1016/j.arabjc.2014.11.021
Chemistry of 4-hydroxy-2(1H)-quinolone
5 O
OH
O + R
N H 1
O
H N
O OH
N H
+
EtO
OEt
36
35
35,37
O
Ac2O 90°C, 4 h
OEt
O
R
Yield %
a
Ph
71
b
Me
46
c
2-Pyrazinyl
9
d
3-Pyridinyl
31
R
N H 37
O
Scheme 12
O O
OH + N H 1
H N
O
Ph NEt , pyridine 3
N
EtO
O
Reflux, 4h
O 38
Ph O
N O H 39 (69%)
Scheme 13
2.3.2. Pyranoquinolines
O O
O
OH O + N H 1
O
O
O
Et
Pyridine, DMF Heating, 5h
O 40
N O H 41 (58 %)
Scheme 14
O
N H 1
R
O
OH R NaOEt, EtOH
+ EtO O
reaction of N-benzilidenenaphthalen-2-amines 26 and 4hydroxy-2(1H)-quinolone 1 in aqueous media catalyzed by triethylbenzylammonium chloride (TEBAC) (Wang et al., 2005) (Scheme 9). Though the detailed mechanism of the above reaction has not been clarified yet, the formation of 27 can be explained by the possible mechanism presented in Scheme 10.
CN
N H 43
42
O
R: CN, COOEt.
Scheme 15
Pyranoquinolines are the main constituent unit of the many of the alkaloids of the plant family Rutaceae (Manske and Rodrigo, 1988; Sainsbury, 1978; Chen et al., 1997; Wabo et al., 2005; Michael, 2002, 2003, 2004, 2005) and have gained much importance because of their interesting pharmacological properties and synthetic applications (Chen et al., 1994; Barr et al., 1995; Nahas and Abdel-Hafez, 2005; Amin, 1993; Magesh et al., 2004; Schiemann et al., 2007). 2.3.2.1. Angular pyranoquinolines. 2.3.2.1.1. Pyrano[3,2c]quinoline-2,5(2H,6H)-diones. Many methods for the synthesis of pyrano[3,2-c]quinoline-2,5(2H,6H)-dione derivatives have been reported successively. It has been reported that the preparation of 3-acetyl(benzoyl)amino-5,6-dihydropyrano[3,2-c]quinoline-2,5(2H,6H)-dione 34 was accomplished by the treatment of methyl 2-acetyl(benzoyl)amino-3-(N,Ndimethylamino)propenoates 33 with 1 in acetic acid (Ngadjui et al., 1992; Kralj et al., 1997) (Scheme 11). An elegant and efficient one-pot synthesis of acylamino derivatives of quinoline 37 was achieved by the reaction of 35, triethyl orthoformate (TOF) 36 and 4-hydroxy-2(1H)-quinolone 1 in acetic anhydride (Kmetic et al., 1993) (Scheme 12). Kepe et al. (1995) observed that treatment of 4-ethoxymethylene-2-phenyl-5(4H)-oxazolone 38 with 1 under basic conditions in boiling mixtures of pyridine and triethylamine O
OH
O
O
O OEt CH3CO2NH4, nitrobenzene
+ EtO N H 1
O
O
0.5h, 220 °C
44
COOEt N H 45
O
Scheme 16
Please cite this article in press as: Abdou, M.M. Chemistry of 4-hydroxy-2(1H)-quinolone. Part 2. As synthons in heterocyclic synthesis. Arabian Journal of Chemistry (2014), http://dx.doi.org/10.1016/j.arabjc.2014.11.021
6
M.M. Abdou O OH + N H 1
CH3COONH4, nitrobenzene
R2
EtO
R1
200 °C
R1
O
R2
O
O
O
N H 47
46 46, 47
R1
R2
Yield %
a
H
CH3
73 %
b
H
C6H5
47 %
c
CH2-C6H5
CH3
83 %
O
Scheme 17
NH2
R1
R_CHO +
R1 +
N H
R2
O
OH R2
H
O
A,B reflux
N H
CN
1
48,49
R1
R2
Yield% (A/B)
a
H
CN
83/ 70
b
4-N(CH3)2
CN
--/ 63
c
4-OCH3
CN
--/ 65
4-Cl
CN
N H 1
52
COOEt
87 / 67
f
4-CH3
COOEt
90 / --
g
4-OCH3
COOEt
63 / --
h
4-Cl
COOEt
84 / 65
N H 54
R
O 55
N H
NH CN
O
R
O
N H 57
O
N CN
R
79/ 60
H
O
CN
53
_H
NH2 O
NC O
NH4OAC
N H
e
53 O
OH
49
48
d
O
CN
CN 51
50
CN
CN NH OAC R 4
O
CN
O NH4OAC
R N H
O
56
Scheme 20
A : Triethylamine in ethanol, Time= 0.75h, Heating. B : Piperidine in ethanol, Time= 2h, Heating.
Scheme 18
led to N-(5,6-dihydro-2,5-dioxo-2H-pyrano[3,2-clquinoline-3yl)benzamide 39 [50] (Scheme 13). 4-Hydroxy-2(1H)-quinolone 1 when condensed with ethyl2,3-dihydro-3-oxobenzofuran-2-carboxylate 40 afforded the corresponding 6H,12H-benzofuropyrano[3,2-c]quinoline-6,12diones 41 (Kepe et al., 1992) (Scheme 14).
Reaction of ethoxymethylenemalononitrile and ethyl ethoxymethylenecyanoacetate 42, with 4-hydroxy-2(1H)-quinolone 1 led to the corresponding 2,5-dioxo-5,6-dihydro-pyrano[3.2-c]quinolines 43 exhibiting remarkable visible fluorescence (Mulwad et al., 1999) (Scheme 15). Schmidt and Junek (1978) have reported the synthesis of pyrano[3,2-c]quinoline-2,5-diones 45 via the treatment of 4-hydroxy-2(1H)-quinolone 1 with 1-ethoxycarbonylethyliden 44 in nitrobenzene (Scheme 16). The Pechmann-Duisberg reaction was employed by Kappe and Mayer (1981) to synthesize pyrano[3,2-c]quinoline-2, 5-diones 47 via condensation of 1 with b-ketoesters 46 and NH2 CN
+ R-CHO + N H 1
CN
O
OH
CN
O 50
51
EtOH
R N H 52
O
R : CH3CH2, CH3CH2CH2, C6H5, 4-CH3C6H4, 4-CH3OC6H4, 4-FC6H4, 4-HOC6H4, 2-ClC6H4, 4-NO2C6H4, 4-CNC6H4, 4-ClC6H4 , 4-BrC6H4,3-NO2C6H4 , 2,4-Cl2C6H3 , 3,4-Cl2C6H3 , 3,4-OCH2OC6H3, 3- CH3O-4-HOC6H3, 2-Furyl, 4-Pyridyl.
Scheme 19
Please cite this article in press as: Abdou, M.M. Chemistry of 4-hydroxy-2(1H)-quinolone. Part 2. As synthons in heterocyclic synthesis. Arabian Journal of Chemistry (2014), http://dx.doi.org/10.1016/j.arabjc.2014.11.021
Chemistry of 4-hydroxy-2(1H)-quinolone
7
OH
O COOH + (CH2O)n +
N H 1
O
1,4-dioxane N2 atm, 4.5 h
N H
59
58
OH
O
O
60 (82 %)
PPA, xylene 10h, 145 °C
+ O
N H 1
N O H 69 (67%)
68
Scheme 21
Scheme 24
OH
N H 1
H3C R
O
OH + CH3CHO O
Et 2 NH, C 6H 6 Heating, 5h
61
+ N H 1
N O H 62 (51%)
R
A
53
a
H
B
70
b
CH3
A
50
b
CH3
C
70
b
CH3
B
94
c
C2H5
B
77
N H 1
OH
82
A
40
f
CH2-CH2=CH-CH(CH3)2
C
71
O
N H
+
toluene 80-95 0C
N
Cl
O O 72
1
73
H N
O
O
OH
O R
74
R= C6H5, CH2C6H5
Scheme 26
O
OH -H2O
CH3CHO H
N H 64
N H 65
O
O
H, 63
Et OH
O
CH3 OH
RCH=CHNEt2
hydrolysis O
B
CH2-CH2=CH-CH(CH3)2
N
O
N H 62
C3H7
e
+ R
O
Et
d
Cl
O
OH
Condition Yield %
Scheme 25
O
O
O
Conditions: A : Yb(OTf)3, CH3CN, 12h, Heating. B : Ethylenediaminediacetic acid in CH2Cl2, Time= 10h, T= 20 °C. C: Water, 6h, 80 °C.
Using three component condensation: There have been several methods for synthesizing pyranoquinoline derivatives, including the three-component reaction of 4-hydroxy-2(1H)-quinolone 1, aldehydes 50, malononitrile for the synthesis of 2-amino-3-cyano-1,4,5,6-tetrahydropyrano[3,2-c]quinolin-5-one derivatives 52 catalyzed by TEBA (benzyltriethylammonium chloride), piperidine, TsOH, NH2SO3H, SiO2–NaHSO3, ZnCl2, MgCl2, Cu (ClO4)2-6H2O, Et3N, DBU, imidazole, ammonium acetate, KF–Al2O3 and Yb(OTf)3) (Sowellim et al., 1995, 1996; Wang et al., 2004a,b, 2006; Nasseri and Sadeghzadeh, 2013; Lei et al., 2011; Peng et al., 2005; Kumar et al., 2009) (Scheme 19). Recently, Guan et al.
N H 63
N H 71
70
H
2.3.2.1.2. 2-Aminopyrano[3,2-c]quinolin-5-ones.
DEA _H
Various conditions
a
ammonium acetate at 200 C in nitrobenzene (Scheme 17). Also, this reaction can be performed in pyridine instead of nitrobenzene.
Using two component condensation: A number of publications (Kumar and Rajendran, 2004; Dodia and Shah, 2001) have been taken out for Michael reactions of 4-hydroxy-2(1H)quinolone 1 with various substituted acrylonitriles 48 in the presence of base (triethylamine or piperidine) as a catalyst resulting in the corresponding 2-amino-4-aryl-1,4,5,6-tetrahydro-pyrano[3,2-c]quinolin-5-ones 49 (Scheme 18).
R
O
O
70,71
Scheme 22
OH
O
OH
N H 67
O
N H
OO
N H
66
Scheme 23
Please cite this article in press as: Abdou, M.M. Chemistry of 4-hydroxy-2(1H)-quinolone. Part 2. As synthons in heterocyclic synthesis. Arabian Journal of Chemistry (2014), http://dx.doi.org/10.1016/j.arabjc.2014.11.021
8
M.M. Abdou H3C HN
OH O
O N H 1
NaOH 1h
+
+ O O
O
75
HN
H N
O
O
76
O
77
CH3
O
Scheme 27
HN
OH SH N H 1
1 by tandem Knoevenagel condensation with an acetaldehyde 61 in the presence of diethylamine as a base in refluxing benzene (Ye et al., 1999) (Scheme 22). The possible mechanism could account for the formation of product 62 via base-catalyzed condensation of a quinolinone 1 with an acetaldehyde 61 yielding the corresponding 4-hydroxy3-(1-hydroxyethyl)quinolin-2-one 64, which is dehydrated on heating in the basic reaction medium to furnish the highly electrophilic quinone methide intermediate 65. The quinone methide 65 then undergoes competitive Michael-type addition of the enamine proceeds in a 1,4-fashion and results in an intramolecular cyclization to give the 2-(diethylamino) pyrano-[3,2-c]quinolin-5-one 66, which on hydrolysis during the reaction affords the final product 62 (Scheme 23). An efficient synthesis of pyranoquinoline alkaloids is described by Thangavel et al. (2007) via direct treatment of isoprene 68 with 4-hydroxy-2(1H)-quinolone 1 in the presence of polyphosphoric acid, furnishing dihydroflindersine 69 in good yield (Scheme 24). 2.3.2.1.4. Miscellaneous pyrono quinolone. In water medium, environmentally benign, facile, and efficient synthesis of pyrans 71 was achieved in good yields by domino Knoevenagel reaction of 1 with several a,b-unsaturated aldehydes 70 (Jung et al., 2010) (Scheme 25). This method has been successfully applied to the synthesis of biologically interesting and naturally occurring pyranoquinolinone alkaloids in good yields. Also, this reaction can be achieved by ytterbium(III) triflate (Lee et al., 2001) or ethylenediaminediacetic acid in dichloromethane (Wang and Yong, 2007).
+ O
S
DMF
. NH2 120 °C, 12h
N H
O
79
78
Scheme 28
(2013) found that 2-amino-3-cyano-1,4,5,6-tetrahydropyrano[3,2-c]quinolin-5-one derivatives 52 could be prepared without catalyst in a mixed solvent of ethanol and water. The condensation of 1, aldehyde 50, malononitrile 51 may occur by a mechanism of Knoevenagel condensation, Michael addition, intramolecular cyclization, and isomerization. Initially, intermediate 53 is formed by Knoevenagel condensation of aldehyde 50 and malononitrile 51 by the action of ammonium acetate. Then, the proton of 4-hydroxy-2(1H)quinolone 1 is abstracted by ammonium acetate to form intermediate 54. Michael addition of intermediate 54 on 53 leads to the formation of 55, followed by cyclization and isomerization, affords the corresponding 2-amino-4H-pyrano[3,2-c]quinolin-5(6H)-one derivatives 52 (Wang et al., 2004a,b) (Scheme 20). 2.3.2.1.3. 3,4-Dihydrobenzopyrano[3,2-c]quinoIin-5(6H)-one. 2,2-Dimethyl-3,4-dihydropyrano[3,2-c]quinoIin-5(6H)-one 60 was prepared by refluxing a solution of l with para-formaldehyde 58 and 3,3-dimethylacrylic acid 59 in 1,4-dioxane under nitrogen atmosphere for 4.5 h (Suresh et al., 2005) (Scheme 21). 2,3,4,6-Tetrahydro-2-hydroxy-4-methylpyrano[3,2-c]quinolin-5-one 62 are synthesized from 4-hydroxy-2(1H)-quinolone
2.3.2.3. Linear pyranoquinolines. No¨hammer and Kappe (1976) showed that the reaction of 4-hydroxy-2(1H)-quinolone 1 with malonyl chlorides 72 in the presence of N,N-dimethylaniline 73
2
2 1 3
3
1
1
2 3 3
3 3
3 3
Scheme 29
Please cite this article in press as: Abdou, M.M. Chemistry of 4-hydroxy-2(1H)-quinolone. Part 2. As synthons in heterocyclic synthesis. Arabian Journal of Chemistry (2014), http://dx.doi.org/10.1016/j.arabjc.2014.11.021
Chemistry of 4-hydroxy-2(1H)-quinolone yielded the corresponding linear pyronoquinolones 74 (Scheme 26). Sangeetha and Prasad (2006) adopted a novel and highly efficient methodology for synthesizing quinolino[2,3-o]carbazolo[6,5-a]pyran-7,8-diones 77 with interesting biological activity via reaction of 1 with vinyl acetate 75 and 3,11-dihydro-2,4dioxopyrano[2,3-o]carbazoles 76 (Scheme 27). 2.3.3. Quinolinobenzothiazinones One of the most successful strategies for constructing 5H-quinolin[3,4-b][1,4]benzothiazin-6(12H)-one 79 as a new agent with estrogenic activity mediated by estrogen receptors (ER) is the condensation and oxidative cyclization of amino thiophenol 78 with 1 in dioxane in the presence of p-toluene sulfonic acid (Ruano et al., 1991) or N,N-dimethylformamide (Coppola et al., 1981) (Scheme 28). 2.4. [6-6-8-6] ring system 2.4.1. Oxazocines Basic alumina supported and solvent-free synthesis of novel oxazocines 81 has been achieved in excellent yields by tandem C-alkylation followed by intramolecular O-alkylation of 1 with quinolinium salts 80 under microwave irradiation (Mondal et al., 2011) (Scheme 29). 3. Conclusion The data considered in this review clearly demonstrate that 4hydroxy-2(1H)-quinolone may be successfully used to synthesize a wide variety of heterocycles of academic and pharmaceuticals interest. Finally, all chemistry presented here along with that already discussed in my previous review article (Abdou, 2014), clearly demonstrates the utility of 4-hydroxy-2(1H)quinolone for countless organic transformations. Acknowledgements It is a pleasure to acknowledge the contributions made by my co-workers mentioned in the list of references. For financial support, I would like to thank the Academy of Scientific Research and Technology, ASRT, Egypt. Also, the author regrets any omissions that may have occurred in this review. Finally, I would like to thank Professor El-Sayed I. El-Desoky for reading the manuscript and making useful suggestions. References Abbaspour-Gilandeh, E., Azimi, S.C., Rad-Moghadam, K., 2013. Synthesis of novel pyrano[3,2-c]quinoline-2,5-diones using an acidic ionic liquid catalyst. Tetrahedron Lett. 54 (35), 4633–4636. Abdou, M.M., 2014. Chemistry of 4-hydroxy-2(1H)-quinolone. Part 1: synthesis and reactions. Arabian J. Chem.. http://dx.doi.org/ 10.1016/j.arabjc.2014.01.012. Amin, K.M., 1993. New pyrano [3,2-f]quinolines of possible H1– antihistamine and mast cell stabilizing properties. Egypt. J. Pharm. Sci. 34, 741–750. Angeleska, S., Kefalas, P., Detsi, A., 2013. Crude peroxidase from onion solid waste as a tool for organic synthesis. Part III: synthesis of tetracyclic heterocycles (coumestans and benzofuroquinolinones). Tetrahedron Lett. 54 (19), 2325–2328.
9 Bar, G., Parsons, A.F., Thomas, C.B., 2001a. Manganese(III) acetate mediated radical reactions in the presence of an ionic liquid. Chem. Commun. 15, 1350–1351. Bar, G., Parsons, A.F., Thomas, C.B., 2001b. Manganese(III) acetate mediated radical reactions leading to araliopsine and related quinoline alkaloids. Tetrahedron 57 (22), 4719–4728. Bar, G., Bini, F., Parsons, A.F., 2003. CAN-mediated oxidative free radical reactions in an ionic liquid. Synth. Commun. 33 (2), 213– 222. Barr, S.A., Neville, C.F., Grundon, M.F., Boyd, D.R., Malone, J.F., Evans, T.A., 1995. Quinolinone cycloaddition as a potential synthetic route to dimeric quinoline alkaloids. J. Chem. Soc., Perkin Trans. 1 (4), 445–452. Basco, L.K., Mitaku, S., Skaltsounis, A.L., Ravelomanantsoa, N., Tillequin, F., Koch, M., Le Bras, J., 1994. In vitro activities of furoquinoline and acridone alkaloids against Plasmodium falciparum. J. Antimicrob. Agents Chemother. 38 (5), 1169–1171. Chen, I.S., Wu, S.J., Tsai, I.L., Wu, T.S., Pezzuto, J.M., Lu, M.C., Teng, C.M., 1994. Chemical and bioactive constituents from Zanthoxylum simulans. J. Nat. Prod. 57 (9), 1206–1211. Chen, I.S., Tsai, I.W., Teng, C.M., Chen, J.J., Chang, Y.L., Ko, F.N., Pezzuto, J.M., 1997. Pyranoquinoline alkaloids from Zanthoxylum simulans. Phytochemistry 46 (3), 525–529. Coppola, G.M., Kahle, A.D., Shapiro, M.J., 1981. 13C NMR investigation of some hetero-ring substituted 2- and 4-quinolone systems. Org. Magn. Reson. 17 (4), 242–245. Dodia, N., Shah, A., 2001. Synthesis of some tricyclic and tetracyclic ring systems built on 4-hydroxy-2-quinolones. Heterocycl. Commun. 7, 289–294. Ghandi, M., Taghi Nazeri, M., Kubicki, M., 2013. An efficient onepot, regio- and stereoselective synthesis of novel pentacyclic-fused pyrano[3,2,c]chromenone or quinolinone benzosultone derivatives in water. Tetrahedron 69 (24), 4979–4989. Grundon, M.F., Surgenor, S.A., 1978. Asymmetric synthesis and absolute stereochemistry of the alkalies araliopsine, isoplatydesmine, and ribalinine. Dual mechanism for a dihydrofuroquinolone– dihydropyranoquinolone rearrangement. Chem. Commun. 14, 624–626. Guan, Z., He, Y.H., Yao, M.J., 2013. Simple, catalyst-free, one-pot procedure for the synthesis of 2-amino-3-cyano-1,4,5,6-tetrahydropyrano[3,2-c] quinolin-5-one derivatives. Synth. Commun. 43 (15), 2073–2078. Guo, H.Y., Jin, S.S., Wang, H., 2013. Ionic liquid catalyzed one-pot synthesis of novel spiro-2-amino-3-phenylsulfonyl-4H-pyran derivatives. Tetrahedron Lett. 54 (19), 2353–2356. Hajdok, S., Conrad, J., Leutbecher, H., Beifuss, U., Strobel, S., Schleid, T., 2009. The laccase-catalyzed domino reaction between catechols and heterocyclic 1,3-dicarbonyls and the unambiguous structure elucidation of the products by NMR spectroscopy and Xray crystal structure analysis. J. Org. Chem. 74, 7230–7237. Hoecker, J., Gademann, K., 2013. Enantioselective total syntheses and absolute configuration of JBIR-02 and Mer-A2026B. Org. Lett. 15 (3), 670–673. Jung, E.J., Park, B.H., Lee, Y.R., 2010. Environmentally benign, onepot synthesis of pyrans by domino Knoevenagel/6p-electrocyclization in water and application to natural products. Green Chem. 12, 2003–2011. Kappe, T., Mayer, C., 1981. A new modification of the Pechmann reaction. Synthesis 7, 524–526. Kepe, V., Kocevar, M., Petric, A., Polanc, S., Vercek, B., 1992. 4Ethoxymethylene-2-phenyl-5(4H)-oxazolone as a synthon for the synthesis of some 2H-pyran-2-ones. Heterocycles 33, 843–849. Kepe, V., Kocevar, M., Polanc, S., 1995. One-pot synthesis of some fused pyran-2-ones. Heterocycles 41, 1299–1306. Kmetic, M., Stanovnik, B., Tisler, M., Kappe, T., 1993. Reaction of methyl 2-benzoylamino-3-dimethylaminopropenoate with heterocyclic hydroxy compounds. The synthesis of fused pyranoazines. Heterocycles 35, 1331–1339.
Please cite this article in press as: Abdou, M.M. Chemistry of 4-hydroxy-2(1H)-quinolone. Part 2. As synthons in heterocyclic synthesis. Arabian Journal of Chemistry (2014), http://dx.doi.org/10.1016/j.arabjc.2014.11.021
10 Kralj, L., Hvala, A., Svete, J., Golic, L., Stanovnik, B., 1997. Aminoacids in the synthesis of heterocyclic systems. The synthesis of methyl 2-acetylamino-3-dimethylaminopropenoate and 2-(Nmethyl-N-trifluoroacetyl)amino-3-dimethylamino propenoate and their application in the synthesis of heterocyclic compounds. J. Heterocycl. Chem. 34 (1), 247–255. Kumabe, R., Nishino, H., 2004. Convenient route to 2H-furo[3,2c]quinolin-4-one framework using Mn(III)-based oxidative radical cyclization. Heterocycl. Commun. 10, 135–138. Kumar, N.V., Rajendran, S.P., 2004. A one-pot synthesis of 4methylpyrano[3,2-c]quinolin-2,5[6H]-diones. Heterocycl. Commun. 10, 289–294. Kumar, D., Reddy, V.B., Sharad, S., Dube, U., Kapur, S., 2009. A facile one-pot green synthesis and antibacterial activity of 2-amino4H-pyrans and 2-amino-5-oxo-5,6,7,8-tetrahydro-4H-chromenes. Eur. J. Med. Chem. 44 (9), 3805–3809. Lee, Y.R., Kirn, B.S., Kweon, H., 2000. Efficient synthesis of dihydrofuroquinolinones and furoquinolinones by Silver(I)/Celite promoted oxidative cycloaddition. Tetrahedron 56, 3867–3874. Lee, Y.R., Kweon, H., Koh, W.S., Min, K.R., Kim, Y., Lee, S.H., 2001. One-pot preparation of pyranoquinolinones by ytterbium(III) trifluoromethanesulfonate-catalyzed reactions: efficient synthesis of Flindersine, N-Methylflindersine, and zanthosimuline natural products. Synthesis 12, 1851–1855. Lei, M., Hu, L., Ma, L., 2011. A green, efficient, and rapid procedure for the synthesis of 2-amino-3-cyano-1,4,5,6-tetrahydropyrano[3,2c]quinolin-5-one derivatives catalyzed by ammonium acetate. Tetrahedron Lett. 52 (20), 2597–2600. Magesh, C.J., Makesh, S.V., Perumal, P.T., 2004. Highly diastereoselective inverse electron demand (IED) Diels–Alder reaction mediated by chiral salen–AlCl complex: the first, target-oriented synthesis of pyranoquinolines as potential antibacterial agents. Bioorg. Med. Chem. Lett. 14 (9), 2035–2040. Manske, R.H.F., Rodrigo, R.G.A., 1988. In: The Alkaloids, vol. XVII. Academic Press, London, p. 105. Michael, J.P., 2002. Quinoline, quinazoline and acridone alkaloids. Nat. Prod. Rep. 19 (6), 742–760. Michael, J.P., 2003. Quinoline, quinazoline and acridone alkaloids. Nat. Prod. Rep. 20 (5), 476–493. Michael, J.P., 2004. Quinoline, quinazoline and acridone alkaloids. Nat. Prod. Rep. 21 (5), 650–668. Michael, J.P., 2005. Quinoline, quinazoline and acridone alkaloids. Nat. Prod. Rep. 22 (5), 627–646. Mondal, S., Paira, R., Maity, A., Naskar, S., Sahu, K.B., Hazra, A., Saha, P., Banerjee, S., Mondal, N.B., 2011. Basic alumina supported tandem synthesis of bridged polycyclic quinolino/ isoquinolinooxazocines under microwave irradiation. Tetrahedron Lett. 52, 4697–4700. Mulwad, V.V., Hegde, A.S., Suryanarayan, V., 1999. Reaction of hydroxycoumarins and its analogues. Indian J. Chem., Sect. B: Org. Chem. Incl. Med. Chem. 38, 148–151. Nahas, N.M., Abdel-Hafez, A.A., 2005. Synthesis and antibacterial activities of fused pyranoquinoline derivatives. Heterocycl. Commun. 11 (3–4), 263–272. Nasseri, M.A., Sadeghzadeh, S.M., 2013. A highly active FeNi3–SiO2 magnetic nanoparticles catalyst for the preparation of 4Hbenzo[b]pyrans and spirooxindoles under mild conditions. J. Iran. Chem. Soc. 10 (5), 1047–1056. Neve, J.E., Wijesekera, H.P., Duffy, S., Jenkins, I.D., Ripper, J., Teague, S.J., Quinn, R.J., 2014. Euodenine A: a small molecule agonist of human TLR4. J. Med. Chem. 57 (4), 1252–1275. Neville, C.F., Grundon, M.F., Ramachandran, V.N., Reisch, G., Reisch, J., 1991. Quinoline alkaloids. Part 28. The biosynthesis of furoquinolines and other hemiterpenoids in Ptelea trifoliata. J. Chem. Soc. Perkin Trans. 1 (9), 2261–2268. Ngadjui, B.T., Ayafor, J.F., Bilon, A.E., Sondengam, B.L., Connolly, J.D., Rycroft, D.S., 1992. Synthesis of veprisine dimers and the
M.M. Abdou formation of a novel cyclic tetramer from precocene I. Tetrahedron 48 (40), 8711–8724. No¨hammer, G., Kappe, T., 1976. Zur Reaktion von 4-Hydroxy-2chinolon mit reaktiven Malonsa¨urederivaten. Monatsh. Chem. 107 (4), 859–863. Pandey, G., Muralikrishna, C., Bhalerao, U.T., 1989. Mushroom tyrosinase catalysed synthesis of coumestans, benzofuran derivatives and related heterocyclic compounds. Tetrahedron 45, 6867–6874. Peng, Y., Song, G., Huang, F., 2005. Tetramethylguanidine[bmim][BF4]. An efficient and recyclable catalytic system for onepot synthesis of 4H-pyrans. Monatsh. Chem. 136 (5), 727–731. Rao, V.S., Darbarwar, M., 1989. A facile synthesis of 2-methyl-4-oxo4,5-dihydrofuro[3,2-] quinolines. Synthesis 1989 (2), 139–141. Ruano, J.L.G., Pedregal, C., Rodriguez, J.H., 1991. Synthesis and tautomerism of 2,4-dihydroxyquinolines. Heterocycles 32, 2151– 2159. Sainsbury, M., 1978. In: Coffey, S. (Ed.), . In: Rodd’s Chemistry of Carbon Compounds, vol. IVG. Elsevier, New York, p. 171. Sangeetha, V., Prasad, K.J.Rajendra, 2006. Synthesis of 12,13-dihydro-5-oxoquinolino[2,3-a]carbazoles, 3,11-dihydro-2,4-dioxopyrano[2,3-a]carbazoles and quinolino[2,3-b]carbazolo[6,5-a]pyran7,8-diones. Indian J. Chem., Sect. B: Org. Chem. Incl. Med. Chem. 45, 1487–1491. Schiemann, K., Emde, U., Schlueter, T., Saal, C., Maiwald, M. 2007. Preparation of polymorphic forms of pyranoquinolines for treatment of proliferative diseases. Int. Patent WO, 2007147480, A2, Chem. Abstr. 2007, 148, 85962. Schmidt, H.W., Junek, H., 1978. Cyclisierungsreaktionen zu Pyrano [3,2-c] pyridinen und pyrano [3,2-c] chinolinen unter Verwendung von Ethoxymethylen-malodinitril bzw.-cyanessigester Synthesen mit Nitrilen, 50. Mitt. pyrano [3,2-c] quinolines with ethoxymethylene-malonitrile and-ethyl cyanoacetate, resp. Monatsh. Chem. 109 (5), 1075–1080. Senboku, H., Takashima, M., Suzuki, M., Kobayashi, K., Suginome, H., 1996. Photoinduced molecular transformations. Part 159. Formation of some furonaphthyridinones by selective b-scission of cyclobutanoxyl radicals generated from [2+2] photoadducts of 4-hydroxy-1-phenyl [1,8] naphthyridin-2(1H)-one with alkenes. Tetrahedron 52 (17), 6125–6138. Shobana, N., Shanmugam, P., 1986. Sodium hydrogen telluride – a new convenient reagent for deblocking allyl carboxylates and allyl phenyl ethers. Indian J. Chem., Sect. B: Org. Chem. Incl. Med. Chem. 25 (6), 658-658. Shobana, N., Amirthavalli, M., Deepa, V., Shanmugam, P., 1988. Sodium hydrogen telluride- an efficient reagent for deblocking of aryl ethyl carbonates. Indian J. Chem., Sect. B: Org. Chem. Incl. Med. Chem. 27, 965–966. Sowellim, S.I.A., EI-Taweel, F.M.A., Elagamey, A., 1995. Cyclization reactions of a, b-unsaturated nitriles with quinoline and cinnoline derivatives: new approaches for synthesis of 4H-pyrano[3,2-c]quinoline and 4H-pyrano[3,2-c]cinnoline derivatives. Egypt. J. Chem. 38, 511. Sowellim, S.Z.A., El-Taweel, F.M.A.A., Elagamey, A.G.A., 1996. Activated nitriles in organic synthesis: synthesis of pyranoquinolinone, 6H-2-benzopyrano[4,3-c]quinolinone and thieno[2,3-b]pyridine. Bull. Soc. Chim. Fr. 133, 229–234. Subramanian, M., Mohan, P.S., Shanmugam, P., Prasad, K.J., Rajendra, Z., 1992. Quinoline alkaloids. Synthesis of khaplofoline, ribalinine, and flindersine. Naturforsch. B 47 (7), 1016–1020. Suginome, H., Kobayashi, K., Itoh, M., Seko, S., Furusaki, A., 1990. Photoinduced molecular transformations. 110. Formation of furoquinolinones via .beta.-scission of cyclobutanoxyl radicals generated from [2 + 2] photoadducts of 4-hydroxy-2-quinolone and acyclic and cyclic alkenes. X-ray crystal structure of (6a.alpha., 6b.beta., 10a.beta., 10b.alpha.)-(+)-10b-acetoxy-6a,6b,7,8,9,10, 10a,10b-octa hydro-5-methylbenzo[3,4]cyclobuta[1,2-c]quinolin6(5H)-one. J. Org. Chem. 55 (16), 4933–4943.
Please cite this article in press as: Abdou, M.M. Chemistry of 4-hydroxy-2(1H)-quinolone. Part 2. As synthons in heterocyclic synthesis. Arabian Journal of Chemistry (2014), http://dx.doi.org/10.1016/j.arabjc.2014.11.021
Chemistry of 4-hydroxy-2(1H)-quinolone Suginome, H., Seko, S., Konishi, A., Kobayashi, K., 1991. One-step formation of furo [3, 2-c] quinolin-4 (5H)-ones by a new regioselective [2+3] photoaddition of methoxy-substituted 4-hydroxyquinolin-2-one with alkenes1. Tetrahedron Lett. 32 (38), 5115–5118. Suresh, T., Dhanabal, T., Nandha Kumar, R., Mohan, P.S., 2005. Synthesis of pyranoquinoline alkaloids via (4+2) cycloaddition reaction. Heterocycl. Commun. 11, 79–84. Svoboda, G.H., Poore, G.A., Simpson, P.J., Boder, G.B., 1966. Alkaloids of Acronychia Baueri Schott I: isolation of the alkaloids and a study of the antitumor and other biological properties of acronycine. J. Pharm. Sci. 55 (8), 758–768. Tabakovic, I., Grujic, Z., Bejtovic, Z., 1983. Electrochemical synthesis of heterocyclic compounds. XII. Anodic oxidation of catechol in the presence of nucleophiles. J. Heterocycl. Chem. 20, 635–638. Thangavel, D., Ravindran, S., Moonsamy, G.R., Palathurai, M.S., 2007. Simple efficient synthesis of pyranoquinoline alkaloids: flindersine, khaplofoline, haplamine and their analogues. J. Chem. Res., Synop. 2, 124–126. Ukrainets, I.V., Sidorenko, L.V., Gorokhova, O.V., Slobodzyan, S.V., 2006. 4-Hydroxy-2-quinolones. 97. Simple synthesis of the esters of 4-halo-substituted 2-oxo-1,2-dihydroquinoline-3-carboxylic acids. Chem. Heterocycl. Compd. 42 (7), 882–885. Wabo, H.K., Tane, P., Connolly, J.D., Okunji, C.C., Schuster, B.M., Iwu, M.M., 2005. Tabouensinium chloride, a novel quaternary pyranoquinoline alkaloid from Araliopsis tabouensis. Nat. Prod. Res. 19 (6), 591–595. Wang, X., Yong, R.L., 2007. Efficient synthesis of substituted pyranoquinolinones from 2,4-dihydroxyquinoline: total synthesis
11 of zanthosimuline, cis-30 ,40 -dihydroxy-30 ,40 -dihydroflindersine, and orixalone. Synthesis 19, 3044–3050. Wang, X.S., Zeng, Z.S., Shi, D.Q., Tu, S.J., Wei, X.Y., Zong, Z.M., 2004a. Study on the reaction of arylmethylidenemalononitriles with 4-hydroxy-1,2-dihydroquinolin-2-one. Chin. J. Org. Chem. 24 (12), 1595–1597. Wang, X., Zeng, Z., Shi, D., Wei, X., Zong, Z., 2004b. One-step synthesis of 2-amino-3-cyano-4-aryl-1,4,5,6-tetrahydropyrano[3,2c]quinolin-5-one derivatives using KF-Al2O3 as catalyst. Synth. Commun. 34, 3021–3027. Wang, X.S., Zhang, M.M., Zeng, Z.S., Shi, D.Q., Tu, S.J., Wei, X.Y., Zong, Z.M., 2005. A Clean procedure for the synthesis of chromeno[4,3-b]benzo[f]quinoline and quinolino[4,3-b]benzo[f] quinoline derivatives in aqueous media. Chem. Lett. 34 (10), 1316–1317. Wang, X.S., Zeng, Z.S., Li, Y.L., Shi, D.Q., Tu, S.J., Wei, X.Y., Zong, Z.M., 2006. Synthesis of 2-amino-4-aryl-5, 6-dihydro-4H-pyrano [3,2-c] quinolin-5-one derivatives in water. Chin. J. Org. Chem. 26 (2), 228–232. Wolters, B., Eilert, U., 1981. Antimicrobial substances in callus cultures of Ruta graveolens. Planta Med. 43 (10), 166–174. Ye, J.H., Ling, K.Q., Zhang, Y., Li, N., Xu, J.H., 1999. Syntheses of 2-hydroxypyrano[3,2-c]quinolin-5-ones from 4-hydroxyquinolin2-ones by tandem Knoevenagel condensation with aldehyde and Michael addition of enamine with the quinone methide-thermoand photochemical approaches. J. Chem. Soc., Perkin Trans. 1 (14), 2017–2024.
Please cite this article in press as: Abdou, M.M. Chemistry of 4-hydroxy-2(1H)-quinolone. Part 2. As synthons in heterocyclic synthesis. Arabian Journal of Chemistry (2014), http://dx.doi.org/10.1016/j.arabjc.2014.11.021
King Saud University
Arabian Journal of Chemistry www.ksu.edu.sa www.sciencedirect.com
REVIEW
Chemistry of 4-hydroxy-2(1H)-quinolone. Part 2. As synthons in heterocyclic synthesis Moaz M. Abdou
*
Egyptian Petroleum Research Institute, Nasr City, P.O. 11727, Cairo, Egypt Received 2 June 2014; accepted 3 November 2014
KEYWORDS 4-Hydroxy-2(1H)-quinolone; Heterocycles; Microwave irradiation; Ionic liquid; Multicomponent reactions; Electrochemical routes
Abstract This review presents a systematic and comprehensive survey of the utility of 4-hydroxy2(1H)-quinolone as a building block of heterocyclic compounds. The reaction mechanism is considered as well as the scope and limitation of the most important of these approaches are demonstrated. ª 2014 The Author. Production and hosting by Elsevier B.V. on behalf of King Saud University. This is an open access article under the CC BY-NC-ND license (http://creativecommons.org/licenses/by-nc-nd/3.0/).
Contents 1. 2.
3.
Introduction . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . Synthesis of fused heterocyclic compounds . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 2.1. [6-6-5] ring system. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 2.1.1. Dihydrofuran and furoquinolinones . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 2.2. [6-6-5] ring system. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 2.3. Fused [6-6-6] ring system . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 2.3.1. Quinolino[4,3-b]benzo[f]quinolin-6-one . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 2.3.2. Pyranoquinolines . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 2.3.3. Quinolinobenzothiazinones . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 2.4. [6-6-8-6] ring system . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 2.4.1. Oxazocines . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . Conclusion . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
00 00 00 00 00 00 00 00 00 00 00 00
* Tel.: +20 1000409279. E-mail address: [email protected]. Peer review under responsibility of King Saud University.
Production and hosting by Elsevier http://dx.doi.org/10.1016/j.arabjc.2014.11.021 1878-5352 ª 2014 The Author. Production and hosting by Elsevier B.V. on behalf of King Saud University. This is an open access article under the CC BY-NC-ND license (http://creativecommons.org/licenses/by-nc-nd/3.0/). Please cite this article in press as: Abdou, M.M. Chemistry of 4-hydroxy-2(1H)-quinolone. Part 2. As synthons in heterocyclic synthesis. Arabian Journal of Chemistry (2014), http://dx.doi.org/10.1016/j.arabjc.2014.11.021
2
M.M. Abdou Acknowledgements . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 00 References . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 00
1. Introduction 4-Hydroxy-2(1H)-quinolone is a versatile and convenient precursor for the synthesis of a wide variety of heterocyclic compounds (Ghandi et al., 2013; Guo et al., 2013; Abbaspour-Gilandeh et al., 2013; Neve et al., 2014; Hoecker and Gademann, 2013). It is of particular interest as a very promising reagent for cascade heterocyclization, which will undoubtedly become one of the main approaches to the targeted synthesis of heterocycles in the near future, in the rapidly-rising field of combinatorial chemistry. This new methodology based on automatic, high-tech synthetic methods enables synthesis of a large number of novel organic compounds as subjects for biological screening. The first part of this review article (Abdou, 2014) is concerned with the progress in 4-hydroxy-2(1H)-quinolone chemistry and deals with the synthesis, chemical reactivity and reactions of 4-hydroxy-2(1H)-quinolone. This second part systematizes the application of 4-hydroxy-2(1H)-quinolone in heterocyclic synthesis. The enolic reactive center in this compound provides ample opportunities to synthesize a great variety of novel compounds under relatively mild conditions and using simple laboratory equipment. Thus, the two parts are complementary and display current trends in 4-hydroxy2(1H)-quinolone chemistry. In the literature survey, the reactions involving 4-hydroxy2(1H)-quinolone occur with regioselectivity and its course can easily be controlled by changing reaction conditions and varying substituents in the molecules of initial compounds. The heterocyclic compounds are obtained in a single step with high yield and they are reported in order of the increase of (i) the number of rings, (ii) the size of such rings and (iii) the number of heteroatoms present. The sequence of heteroatoms followed is: nitrogen, oxygen and sulfur. The site of fusion in fused heterocycles is indicated by numbers and letters and the numbering of the heterocyclic ring systems is that reported by chemical abstracts.
and furoquinolinones have been well reported (Senboku et al., 1996; Suginome et al., 1990, 1991; Rao and Darbarwar, 1989; Neville et al., 1991; Grundon and Surgenor, 1978). 2.1.1.1. Oxidative cycloaddition reaction mediated by metal salts. The oxidative addition reaction of carbon-centered radicals to alkenes mediated by metal salts Ag(1), Ce(IV) and Mg(II) has received considerable attention over the last decade in organic synthesis for the construction of carbon– carbon bonds. 2.1.1.1.1. Using Ag (1). Lee et al. (2000) have reported that a facile and simple method for the synthesis of dihydrofuran, 2-ethoxy-3,5-dihydro-2H-furo[3,2-c]quinolin-4-one 3, is mediated by the oxidative cyclization of 4-hydroxy-2(1H)-quinolone 1 with ethyl vinyl ether 2 and silver(I)/Celite (Fetizon reagent) in acetonitrile under reflux (Scheme 1). Although the exact mechanism of the reaction is not clear yet, it is best described as shown in Scheme 2. The starting material 1 is first oxidized by one equivalent of Ag(I) to generate the radical 4, which then attacks olefin 2 to give the radical adduct 5. The adduct 5 now undergoes fast oxidation by another one equivalent of Ag(I) to a carbocation 6. Cyclization of the carbocation 6 furnishes intermediate 7, whose deprotonation affords the product 3 (Scheme 2). 2.1.1.1.2. Using Ce(IV). There has been a considerable interest in the use of CAN oxidation reactions in ionic liquids. Hence, reaction of 1 with a-methylstyrene 8 and cerium(IV) ammonium nitrate (CAN) mediated 1-n-butyl-3-methylimidazolium tetrafluoroborate[bmim][BF4]-dichloromethane (1:9), gave tricycles 9,10 (Bar et al., 2003) (Scheme 3). 2.1.1.1.3. Manganese(III) acetate. Mn(III)-based oxidative radical cyclization of 4-hydroxy-2(1H)-quinolone 1 with OEt O
OH + N H 1
OEt
O
Ag2CO3 / Celite acetonitrile/ reflux
N H 3
2
O
2. Synthesis of fused heterocyclic compounds Scheme 1
2.1. [6-6-5] ring system 2.1.1. Dihydrofuran and furoquinolinones Dihydrofuroquinolinone and furoquinolinone alkaloids are widely distributed in nature (Subramanian et al., 1992; Shobana and Shanmugam, 1986; Shobana et al., 1988; Ukrainets et al., 2006). They are primarily isolated from Rutaceae species as an angularly and linearly fused structure. They are reported to have various biological activities such as antimicrobial, antimalarial, insecticidal, antineoplastic, antidiuretic, antiarrhythmic and sedative (Wolters and Eilert, 1981; Svoboda et al., 1966; Basco et al., 1994). This wide range of biological properties has stimulated interest in the synthesis of dihydrofuroquinolinone and furoquinolinone derivatives. A number of synthetic approaches to dihydrofuroquinolinones
O
OH
.
Ag (I) N H
O
N H
Ag (0)
1 + OEt
Ag (I) Ag (0)
2 O
N H
4 O
OEt
O + N H
O
O
5
-H+ N H 6
. OEt
O
3
O
7
Scheme 2
Please cite this article in press as: Abdou, M.M. Chemistry of 4-hydroxy-2(1H)-quinolone. Part 2. As synthons in heterocyclic synthesis. Arabian Journal of Chemistry (2014), http://dx.doi.org/10.1016/j.arabjc.2014.11.021
Chemistry of 4-hydroxy-2(1H)-quinolone
3 Ph
O
OH CAN-[bmim][BF4]
+ N H 1
+
CH2Cl2 / 40o C
O
OH
N
N
OH
Ph
10 (35%)
9 (42%)
8
O
Scheme 3
1,1-diphenylethene 11 in boiling glacial acetic acid afforded 3,5-dihydro-2H-furo[3,2-c]quinolin-4-one 12 (Kumabe and Nishino, 2004) (Scheme 4). Despite the uncertainty related to the reaction mechanism, the authors point toward manganese(III) that could oxidize tertiary carbon radical 14 to afford the corresponding carbocations 15, 16 which were converted into compound 12 (Scheme 5).
Ph Ph
+ N H
Mn(OAc)3 Ph AcOH/100oC
Ph
N H
O
O
12 (73%)
11
1
2.2. [6-6-5] ring system Laccase (Agaricus bisporus)-catalyzed domino reaction of 4hydroxy-2(1H)-quinolone 1 with catechols 20 using aerial oxygen as the oxidant delivers for the synthesis of 10-substituted 8,9-dihydroxybenzofuro[3,2-c]quinolin-6(5H)-ones 21 as single regioisomers with yields ranging from 61% to 77% (Hajdok et al., 2009) (Scheme 7). Some of these compounds have been made accessible by other methods, including tyrosinase-catalyzed oxidation, electrochemical oxidation or crude peroxidase
O
OH
A similar, manganese(III)-mediated reaction using 4hydroxy-2(1H)-quinolone 1 and the alkenes 17 in [bmim] [BF4]–dichloromethane gave a 1:1 mixture of the angular and linear tricycles 18 and 19, respectively (Bar et al., 2001a,b) (Scheme 6).
Scheme 4 R
O
OH
Mn(III) O
Mn(OAc)3 N H
O
OH
Ph . Ph
OH
11
AcOH, reflux
N H
O
N H 14
13
1
Ph
Ph + Ph O Mn(OAc)3 N H 15
-H+
N H
O
O
O
OH 20
Ph
O +
AcOH, reflux
12
O
16
Scheme 5
OH N H 21
O
Yield %
20, 21
R
t/h
a
H
20
73
b
Me
18
77
c
OMe
20
61
Scheme 7
R1 OH
O +
N H 1
cat. laccase, O2 pH=6.0, r.t.
+ N H 1
OH
O
R
O
R2
Mn(OAc)3, 40 C
R1
[bmim][BF4]:CH2Cl2
R2
o
+ N
17
18
17, 18, 19
R1
R2
Yield% (18/19)
a
Ph
H
41/39
b
Me
Ph
41/34
H
71/8
Me
41/4
c d
C 3H 7 C6H 13
OH
OH
N
O
R2 R1
19
Scheme 6
Please cite this article in press as: Abdou, M.M. Chemistry of 4-hydroxy-2(1H)-quinolone. Part 2. As synthons in heterocyclic synthesis. Arabian Journal of Chemistry (2014), http://dx.doi.org/10.1016/j.arabjc.2014.11.021
4
M.M. Abdou OH OH
O
O
oxidation
OH
O
-2e, -2H
20a
N
H N
22
+ _ OH
_
OH O
N H 1
N H 23
22 _ OH
_
O N H 24
N H
OH
1
O
MeO
O
AcOH
O
O
R
N H
O
34
R= OMe, Ph
Scheme 11 OH
O
benzoquinone 22, which then undergoes an intermolecular 1,4-addition with the enol of 1 as a nucleophile to yield 23. A second laccase-catalyzed oxidation to the quinone intermediate (24) which further undergoes an intramolecular 1,4-addition to produce the final tetracyclic heterocycles.
OH
1,4-addition
O
N H 25
O
Scheme 8
2.3. Fused [6-6-6] ring system
from onion solid waste (Pandey et al., 1989; Tabakovic et al., 1983; Angeleska et al., 2013). The reaction is postulated to proceed through a domino process involving several steps (Scheme 8). Initially, the laccase-catalyzed oxidation of the catechol 20 with O2 to
2.3.1. Quinolino[4,3-b]benzo[f]quinolin-6-one A short and simple synthesis of quinolino[4,3-b]benzo[f]quinoline derivatives 27 was accomplished in high yields via the
HN
OH
R TEBAC H2 Ol100 oC
N
+ N H
R
33
O
O
oxidation -2e, -2H
1,4-addition
O
O
OH
H N
O
O
N H
R
27
26
1
O
26, 27
a
b
c
d
e
f
g
h
Ar
2-Cl
4-Cl
3,4-Cl 2
2,4-Cl 2
4-F
4-Br
4-CH 3
3-Cl
Time/ h
8
8
8
8
8
10
12
10
Yield %
94.2
90.2
93.2
97.0
92.5
93.5
91.6
87.8
Scheme 9
OH
OH
Ph
N H 28
O
N
Ph
N H
+ N H 1
O 26
OH
H2 O
NH2
Ph
H2 N O
OH 30 N H
O
N H 31
29
HN
HO HN Ph N H
O
O
-H2O
Ph N H
O
27
32
Scheme 10
Please cite this article in press as: Abdou, M.M. Chemistry of 4-hydroxy-2(1H)-quinolone. Part 2. As synthons in heterocyclic synthesis. Arabian Journal of Chemistry (2014), http://dx.doi.org/10.1016/j.arabjc.2014.11.021
Chemistry of 4-hydroxy-2(1H)-quinolone
5 O
OH
O + R
N H 1
O
H N
O OH
N H
+
EtO
OEt
36
35
35,37
O
Ac2O 90°C, 4 h
OEt
O
R
Yield %
a
Ph
71
b
Me
46
c
2-Pyrazinyl
9
d
3-Pyridinyl
31
R
N H 37
O
Scheme 12
O O
OH + N H 1
H N
O
Ph NEt , pyridine 3
N
EtO
O
Reflux, 4h
O 38
Ph O
N O H 39 (69%)
Scheme 13
2.3.2. Pyranoquinolines
O O
O
OH O + N H 1
O
O
O
Et
Pyridine, DMF Heating, 5h
O 40
N O H 41 (58 %)
Scheme 14
O
N H 1
R
O
OH R NaOEt, EtOH
+ EtO O
reaction of N-benzilidenenaphthalen-2-amines 26 and 4hydroxy-2(1H)-quinolone 1 in aqueous media catalyzed by triethylbenzylammonium chloride (TEBAC) (Wang et al., 2005) (Scheme 9). Though the detailed mechanism of the above reaction has not been clarified yet, the formation of 27 can be explained by the possible mechanism presented in Scheme 10.
CN
N H 43
42
O
R: CN, COOEt.
Scheme 15
Pyranoquinolines are the main constituent unit of the many of the alkaloids of the plant family Rutaceae (Manske and Rodrigo, 1988; Sainsbury, 1978; Chen et al., 1997; Wabo et al., 2005; Michael, 2002, 2003, 2004, 2005) and have gained much importance because of their interesting pharmacological properties and synthetic applications (Chen et al., 1994; Barr et al., 1995; Nahas and Abdel-Hafez, 2005; Amin, 1993; Magesh et al., 2004; Schiemann et al., 2007). 2.3.2.1. Angular pyranoquinolines. 2.3.2.1.1. Pyrano[3,2c]quinoline-2,5(2H,6H)-diones. Many methods for the synthesis of pyrano[3,2-c]quinoline-2,5(2H,6H)-dione derivatives have been reported successively. It has been reported that the preparation of 3-acetyl(benzoyl)amino-5,6-dihydropyrano[3,2-c]quinoline-2,5(2H,6H)-dione 34 was accomplished by the treatment of methyl 2-acetyl(benzoyl)amino-3-(N,Ndimethylamino)propenoates 33 with 1 in acetic acid (Ngadjui et al., 1992; Kralj et al., 1997) (Scheme 11). An elegant and efficient one-pot synthesis of acylamino derivatives of quinoline 37 was achieved by the reaction of 35, triethyl orthoformate (TOF) 36 and 4-hydroxy-2(1H)-quinolone 1 in acetic anhydride (Kmetic et al., 1993) (Scheme 12). Kepe et al. (1995) observed that treatment of 4-ethoxymethylene-2-phenyl-5(4H)-oxazolone 38 with 1 under basic conditions in boiling mixtures of pyridine and triethylamine O
OH
O
O
O OEt CH3CO2NH4, nitrobenzene
+ EtO N H 1
O
O
0.5h, 220 °C
44
COOEt N H 45
O
Scheme 16
Please cite this article in press as: Abdou, M.M. Chemistry of 4-hydroxy-2(1H)-quinolone. Part 2. As synthons in heterocyclic synthesis. Arabian Journal of Chemistry (2014), http://dx.doi.org/10.1016/j.arabjc.2014.11.021
6
M.M. Abdou O OH + N H 1
CH3COONH4, nitrobenzene
R2
EtO
R1
200 °C
R1
O
R2
O
O
O
N H 47
46 46, 47
R1
R2
Yield %
a
H
CH3
73 %
b
H
C6H5
47 %
c
CH2-C6H5
CH3
83 %
O
Scheme 17
NH2
R1
R_CHO +
R1 +
N H
R2
O
OH R2
H
O
A,B reflux
N H
CN
1
48,49
R1
R2
Yield% (A/B)
a
H
CN
83/ 70
b
4-N(CH3)2
CN
--/ 63
c
4-OCH3
CN
--/ 65
4-Cl
CN
N H 1
52
COOEt
87 / 67
f
4-CH3
COOEt
90 / --
g
4-OCH3
COOEt
63 / --
h
4-Cl
COOEt
84 / 65
N H 54
R
O 55
N H
NH CN
O
R
O
N H 57
O
N CN
R
79/ 60
H
O
CN
53
_H
NH2 O
NC O
NH4OAC
N H
e
53 O
OH
49
48
d
O
CN
CN 51
50
CN
CN NH OAC R 4
O
CN
O NH4OAC
R N H
O
56
Scheme 20
A : Triethylamine in ethanol, Time= 0.75h, Heating. B : Piperidine in ethanol, Time= 2h, Heating.
Scheme 18
led to N-(5,6-dihydro-2,5-dioxo-2H-pyrano[3,2-clquinoline-3yl)benzamide 39 [50] (Scheme 13). 4-Hydroxy-2(1H)-quinolone 1 when condensed with ethyl2,3-dihydro-3-oxobenzofuran-2-carboxylate 40 afforded the corresponding 6H,12H-benzofuropyrano[3,2-c]quinoline-6,12diones 41 (Kepe et al., 1992) (Scheme 14).
Reaction of ethoxymethylenemalononitrile and ethyl ethoxymethylenecyanoacetate 42, with 4-hydroxy-2(1H)-quinolone 1 led to the corresponding 2,5-dioxo-5,6-dihydro-pyrano[3.2-c]quinolines 43 exhibiting remarkable visible fluorescence (Mulwad et al., 1999) (Scheme 15). Schmidt and Junek (1978) have reported the synthesis of pyrano[3,2-c]quinoline-2,5-diones 45 via the treatment of 4-hydroxy-2(1H)-quinolone 1 with 1-ethoxycarbonylethyliden 44 in nitrobenzene (Scheme 16). The Pechmann-Duisberg reaction was employed by Kappe and Mayer (1981) to synthesize pyrano[3,2-c]quinoline-2, 5-diones 47 via condensation of 1 with b-ketoesters 46 and NH2 CN
+ R-CHO + N H 1
CN
O
OH
CN
O 50
51
EtOH
R N H 52
O
R : CH3CH2, CH3CH2CH2, C6H5, 4-CH3C6H4, 4-CH3OC6H4, 4-FC6H4, 4-HOC6H4, 2-ClC6H4, 4-NO2C6H4, 4-CNC6H4, 4-ClC6H4 , 4-BrC6H4,3-NO2C6H4 , 2,4-Cl2C6H3 , 3,4-Cl2C6H3 , 3,4-OCH2OC6H3, 3- CH3O-4-HOC6H3, 2-Furyl, 4-Pyridyl.
Scheme 19
Please cite this article in press as: Abdou, M.M. Chemistry of 4-hydroxy-2(1H)-quinolone. Part 2. As synthons in heterocyclic synthesis. Arabian Journal of Chemistry (2014), http://dx.doi.org/10.1016/j.arabjc.2014.11.021
Chemistry of 4-hydroxy-2(1H)-quinolone
7
OH
O COOH + (CH2O)n +
N H 1
O
1,4-dioxane N2 atm, 4.5 h
N H
59
58
OH
O
O
60 (82 %)
PPA, xylene 10h, 145 °C
+ O
N H 1
N O H 69 (67%)
68
Scheme 21
Scheme 24
OH
N H 1
H3C R
O
OH + CH3CHO O
Et 2 NH, C 6H 6 Heating, 5h
61
+ N H 1
N O H 62 (51%)
R
A
53
a
H
B
70
b
CH3
A
50
b
CH3
C
70
b
CH3
B
94
c
C2H5
B
77
N H 1
OH
82
A
40
f
CH2-CH2=CH-CH(CH3)2
C
71
O
N H
+
toluene 80-95 0C
N
Cl
O O 72
1
73
H N
O
O
OH
O R
74
R= C6H5, CH2C6H5
Scheme 26
O
OH -H2O
CH3CHO H
N H 64
N H 65
O
O
H, 63
Et OH
O
CH3 OH
RCH=CHNEt2
hydrolysis O
B
CH2-CH2=CH-CH(CH3)2
N
O
N H 62
C3H7
e
+ R
O
Et
d
Cl
O
OH
Condition Yield %
Scheme 25
O
O
O
Conditions: A : Yb(OTf)3, CH3CN, 12h, Heating. B : Ethylenediaminediacetic acid in CH2Cl2, Time= 10h, T= 20 °C. C: Water, 6h, 80 °C.
Using three component condensation: There have been several methods for synthesizing pyranoquinoline derivatives, including the three-component reaction of 4-hydroxy-2(1H)-quinolone 1, aldehydes 50, malononitrile for the synthesis of 2-amino-3-cyano-1,4,5,6-tetrahydropyrano[3,2-c]quinolin-5-one derivatives 52 catalyzed by TEBA (benzyltriethylammonium chloride), piperidine, TsOH, NH2SO3H, SiO2–NaHSO3, ZnCl2, MgCl2, Cu (ClO4)2-6H2O, Et3N, DBU, imidazole, ammonium acetate, KF–Al2O3 and Yb(OTf)3) (Sowellim et al., 1995, 1996; Wang et al., 2004a,b, 2006; Nasseri and Sadeghzadeh, 2013; Lei et al., 2011; Peng et al., 2005; Kumar et al., 2009) (Scheme 19). Recently, Guan et al.
N H 63
N H 71
70
H
2.3.2.1.2. 2-Aminopyrano[3,2-c]quinolin-5-ones.
DEA _H
Various conditions
a
ammonium acetate at 200 C in nitrobenzene (Scheme 17). Also, this reaction can be performed in pyridine instead of nitrobenzene.
Using two component condensation: A number of publications (Kumar and Rajendran, 2004; Dodia and Shah, 2001) have been taken out for Michael reactions of 4-hydroxy-2(1H)quinolone 1 with various substituted acrylonitriles 48 in the presence of base (triethylamine or piperidine) as a catalyst resulting in the corresponding 2-amino-4-aryl-1,4,5,6-tetrahydro-pyrano[3,2-c]quinolin-5-ones 49 (Scheme 18).
R
O
O
70,71
Scheme 22
OH
O
OH
N H 67
O
N H
OO
N H
66
Scheme 23
Please cite this article in press as: Abdou, M.M. Chemistry of 4-hydroxy-2(1H)-quinolone. Part 2. As synthons in heterocyclic synthesis. Arabian Journal of Chemistry (2014), http://dx.doi.org/10.1016/j.arabjc.2014.11.021
8
M.M. Abdou H3C HN
OH O
O N H 1
NaOH 1h
+
+ O O
O
75
HN
H N
O
O
76
O
77
CH3
O
Scheme 27
HN
OH SH N H 1
1 by tandem Knoevenagel condensation with an acetaldehyde 61 in the presence of diethylamine as a base in refluxing benzene (Ye et al., 1999) (Scheme 22). The possible mechanism could account for the formation of product 62 via base-catalyzed condensation of a quinolinone 1 with an acetaldehyde 61 yielding the corresponding 4-hydroxy3-(1-hydroxyethyl)quinolin-2-one 64, which is dehydrated on heating in the basic reaction medium to furnish the highly electrophilic quinone methide intermediate 65. The quinone methide 65 then undergoes competitive Michael-type addition of the enamine proceeds in a 1,4-fashion and results in an intramolecular cyclization to give the 2-(diethylamino) pyrano-[3,2-c]quinolin-5-one 66, which on hydrolysis during the reaction affords the final product 62 (Scheme 23). An efficient synthesis of pyranoquinoline alkaloids is described by Thangavel et al. (2007) via direct treatment of isoprene 68 with 4-hydroxy-2(1H)-quinolone 1 in the presence of polyphosphoric acid, furnishing dihydroflindersine 69 in good yield (Scheme 24). 2.3.2.1.4. Miscellaneous pyrono quinolone. In water medium, environmentally benign, facile, and efficient synthesis of pyrans 71 was achieved in good yields by domino Knoevenagel reaction of 1 with several a,b-unsaturated aldehydes 70 (Jung et al., 2010) (Scheme 25). This method has been successfully applied to the synthesis of biologically interesting and naturally occurring pyranoquinolinone alkaloids in good yields. Also, this reaction can be achieved by ytterbium(III) triflate (Lee et al., 2001) or ethylenediaminediacetic acid in dichloromethane (Wang and Yong, 2007).
+ O
S
DMF
. NH2 120 °C, 12h
N H
O
79
78
Scheme 28
(2013) found that 2-amino-3-cyano-1,4,5,6-tetrahydropyrano[3,2-c]quinolin-5-one derivatives 52 could be prepared without catalyst in a mixed solvent of ethanol and water. The condensation of 1, aldehyde 50, malononitrile 51 may occur by a mechanism of Knoevenagel condensation, Michael addition, intramolecular cyclization, and isomerization. Initially, intermediate 53 is formed by Knoevenagel condensation of aldehyde 50 and malononitrile 51 by the action of ammonium acetate. Then, the proton of 4-hydroxy-2(1H)quinolone 1 is abstracted by ammonium acetate to form intermediate 54. Michael addition of intermediate 54 on 53 leads to the formation of 55, followed by cyclization and isomerization, affords the corresponding 2-amino-4H-pyrano[3,2-c]quinolin-5(6H)-one derivatives 52 (Wang et al., 2004a,b) (Scheme 20). 2.3.2.1.3. 3,4-Dihydrobenzopyrano[3,2-c]quinoIin-5(6H)-one. 2,2-Dimethyl-3,4-dihydropyrano[3,2-c]quinoIin-5(6H)-one 60 was prepared by refluxing a solution of l with para-formaldehyde 58 and 3,3-dimethylacrylic acid 59 in 1,4-dioxane under nitrogen atmosphere for 4.5 h (Suresh et al., 2005) (Scheme 21). 2,3,4,6-Tetrahydro-2-hydroxy-4-methylpyrano[3,2-c]quinolin-5-one 62 are synthesized from 4-hydroxy-2(1H)-quinolone
2.3.2.3. Linear pyranoquinolines. No¨hammer and Kappe (1976) showed that the reaction of 4-hydroxy-2(1H)-quinolone 1 with malonyl chlorides 72 in the presence of N,N-dimethylaniline 73
2
2 1 3
3
1
1
2 3 3
3 3
3 3
Scheme 29
Please cite this article in press as: Abdou, M.M. Chemistry of 4-hydroxy-2(1H)-quinolone. Part 2. As synthons in heterocyclic synthesis. Arabian Journal of Chemistry (2014), http://dx.doi.org/10.1016/j.arabjc.2014.11.021
Chemistry of 4-hydroxy-2(1H)-quinolone yielded the corresponding linear pyronoquinolones 74 (Scheme 26). Sangeetha and Prasad (2006) adopted a novel and highly efficient methodology for synthesizing quinolino[2,3-o]carbazolo[6,5-a]pyran-7,8-diones 77 with interesting biological activity via reaction of 1 with vinyl acetate 75 and 3,11-dihydro-2,4dioxopyrano[2,3-o]carbazoles 76 (Scheme 27). 2.3.3. Quinolinobenzothiazinones One of the most successful strategies for constructing 5H-quinolin[3,4-b][1,4]benzothiazin-6(12H)-one 79 as a new agent with estrogenic activity mediated by estrogen receptors (ER) is the condensation and oxidative cyclization of amino thiophenol 78 with 1 in dioxane in the presence of p-toluene sulfonic acid (Ruano et al., 1991) or N,N-dimethylformamide (Coppola et al., 1981) (Scheme 28). 2.4. [6-6-8-6] ring system 2.4.1. Oxazocines Basic alumina supported and solvent-free synthesis of novel oxazocines 81 has been achieved in excellent yields by tandem C-alkylation followed by intramolecular O-alkylation of 1 with quinolinium salts 80 under microwave irradiation (Mondal et al., 2011) (Scheme 29). 3. Conclusion The data considered in this review clearly demonstrate that 4hydroxy-2(1H)-quinolone may be successfully used to synthesize a wide variety of heterocycles of academic and pharmaceuticals interest. Finally, all chemistry presented here along with that already discussed in my previous review article (Abdou, 2014), clearly demonstrates the utility of 4-hydroxy-2(1H)quinolone for countless organic transformations. Acknowledgements It is a pleasure to acknowledge the contributions made by my co-workers mentioned in the list of references. For financial support, I would like to thank the Academy of Scientific Research and Technology, ASRT, Egypt. Also, the author regrets any omissions that may have occurred in this review. Finally, I would like to thank Professor El-Sayed I. El-Desoky for reading the manuscript and making useful suggestions. References Abbaspour-Gilandeh, E., Azimi, S.C., Rad-Moghadam, K., 2013. Synthesis of novel pyrano[3,2-c]quinoline-2,5-diones using an acidic ionic liquid catalyst. Tetrahedron Lett. 54 (35), 4633–4636. Abdou, M.M., 2014. Chemistry of 4-hydroxy-2(1H)-quinolone. Part 1: synthesis and reactions. Arabian J. Chem.. http://dx.doi.org/ 10.1016/j.arabjc.2014.01.012. Amin, K.M., 1993. New pyrano [3,2-f]quinolines of possible H1– antihistamine and mast cell stabilizing properties. Egypt. J. Pharm. Sci. 34, 741–750. Angeleska, S., Kefalas, P., Detsi, A., 2013. Crude peroxidase from onion solid waste as a tool for organic synthesis. Part III: synthesis of tetracyclic heterocycles (coumestans and benzofuroquinolinones). Tetrahedron Lett. 54 (19), 2325–2328.
9 Bar, G., Parsons, A.F., Thomas, C.B., 2001a. Manganese(III) acetate mediated radical reactions in the presence of an ionic liquid. Chem. Commun. 15, 1350–1351. Bar, G., Parsons, A.F., Thomas, C.B., 2001b. Manganese(III) acetate mediated radical reactions leading to araliopsine and related quinoline alkaloids. Tetrahedron 57 (22), 4719–4728. Bar, G., Bini, F., Parsons, A.F., 2003. CAN-mediated oxidative free radical reactions in an ionic liquid. Synth. Commun. 33 (2), 213– 222. Barr, S.A., Neville, C.F., Grundon, M.F., Boyd, D.R., Malone, J.F., Evans, T.A., 1995. Quinolinone cycloaddition as a potential synthetic route to dimeric quinoline alkaloids. J. Chem. Soc., Perkin Trans. 1 (4), 445–452. Basco, L.K., Mitaku, S., Skaltsounis, A.L., Ravelomanantsoa, N., Tillequin, F., Koch, M., Le Bras, J., 1994. In vitro activities of furoquinoline and acridone alkaloids against Plasmodium falciparum. J. Antimicrob. Agents Chemother. 38 (5), 1169–1171. Chen, I.S., Wu, S.J., Tsai, I.L., Wu, T.S., Pezzuto, J.M., Lu, M.C., Teng, C.M., 1994. Chemical and bioactive constituents from Zanthoxylum simulans. J. Nat. Prod. 57 (9), 1206–1211. Chen, I.S., Tsai, I.W., Teng, C.M., Chen, J.J., Chang, Y.L., Ko, F.N., Pezzuto, J.M., 1997. Pyranoquinoline alkaloids from Zanthoxylum simulans. Phytochemistry 46 (3), 525–529. Coppola, G.M., Kahle, A.D., Shapiro, M.J., 1981. 13C NMR investigation of some hetero-ring substituted 2- and 4-quinolone systems. Org. Magn. Reson. 17 (4), 242–245. Dodia, N., Shah, A., 2001. Synthesis of some tricyclic and tetracyclic ring systems built on 4-hydroxy-2-quinolones. Heterocycl. Commun. 7, 289–294. Ghandi, M., Taghi Nazeri, M., Kubicki, M., 2013. An efficient onepot, regio- and stereoselective synthesis of novel pentacyclic-fused pyrano[3,2,c]chromenone or quinolinone benzosultone derivatives in water. Tetrahedron 69 (24), 4979–4989. Grundon, M.F., Surgenor, S.A., 1978. Asymmetric synthesis and absolute stereochemistry of the alkalies araliopsine, isoplatydesmine, and ribalinine. Dual mechanism for a dihydrofuroquinolone– dihydropyranoquinolone rearrangement. Chem. Commun. 14, 624–626. Guan, Z., He, Y.H., Yao, M.J., 2013. Simple, catalyst-free, one-pot procedure for the synthesis of 2-amino-3-cyano-1,4,5,6-tetrahydropyrano[3,2-c] quinolin-5-one derivatives. Synth. Commun. 43 (15), 2073–2078. Guo, H.Y., Jin, S.S., Wang, H., 2013. Ionic liquid catalyzed one-pot synthesis of novel spiro-2-amino-3-phenylsulfonyl-4H-pyran derivatives. Tetrahedron Lett. 54 (19), 2353–2356. Hajdok, S., Conrad, J., Leutbecher, H., Beifuss, U., Strobel, S., Schleid, T., 2009. The laccase-catalyzed domino reaction between catechols and heterocyclic 1,3-dicarbonyls and the unambiguous structure elucidation of the products by NMR spectroscopy and Xray crystal structure analysis. J. Org. Chem. 74, 7230–7237. Hoecker, J., Gademann, K., 2013. Enantioselective total syntheses and absolute configuration of JBIR-02 and Mer-A2026B. Org. Lett. 15 (3), 670–673. Jung, E.J., Park, B.H., Lee, Y.R., 2010. Environmentally benign, onepot synthesis of pyrans by domino Knoevenagel/6p-electrocyclization in water and application to natural products. Green Chem. 12, 2003–2011. Kappe, T., Mayer, C., 1981. A new modification of the Pechmann reaction. Synthesis 7, 524–526. Kepe, V., Kocevar, M., Petric, A., Polanc, S., Vercek, B., 1992. 4Ethoxymethylene-2-phenyl-5(4H)-oxazolone as a synthon for the synthesis of some 2H-pyran-2-ones. Heterocycles 33, 843–849. Kepe, V., Kocevar, M., Polanc, S., 1995. One-pot synthesis of some fused pyran-2-ones. Heterocycles 41, 1299–1306. Kmetic, M., Stanovnik, B., Tisler, M., Kappe, T., 1993. Reaction of methyl 2-benzoylamino-3-dimethylaminopropenoate with heterocyclic hydroxy compounds. The synthesis of fused pyranoazines. Heterocycles 35, 1331–1339.
Please cite this article in press as: Abdou, M.M. Chemistry of 4-hydroxy-2(1H)-quinolone. Part 2. As synthons in heterocyclic synthesis. Arabian Journal of Chemistry (2014), http://dx.doi.org/10.1016/j.arabjc.2014.11.021
10 Kralj, L., Hvala, A., Svete, J., Golic, L., Stanovnik, B., 1997. Aminoacids in the synthesis of heterocyclic systems. The synthesis of methyl 2-acetylamino-3-dimethylaminopropenoate and 2-(Nmethyl-N-trifluoroacetyl)amino-3-dimethylamino propenoate and their application in the synthesis of heterocyclic compounds. J. Heterocycl. Chem. 34 (1), 247–255. Kumabe, R., Nishino, H., 2004. Convenient route to 2H-furo[3,2c]quinolin-4-one framework using Mn(III)-based oxidative radical cyclization. Heterocycl. Commun. 10, 135–138. Kumar, N.V., Rajendran, S.P., 2004. A one-pot synthesis of 4methylpyrano[3,2-c]quinolin-2,5[6H]-diones. Heterocycl. Commun. 10, 289–294. Kumar, D., Reddy, V.B., Sharad, S., Dube, U., Kapur, S., 2009. A facile one-pot green synthesis and antibacterial activity of 2-amino4H-pyrans and 2-amino-5-oxo-5,6,7,8-tetrahydro-4H-chromenes. Eur. J. Med. Chem. 44 (9), 3805–3809. Lee, Y.R., Kirn, B.S., Kweon, H., 2000. Efficient synthesis of dihydrofuroquinolinones and furoquinolinones by Silver(I)/Celite promoted oxidative cycloaddition. Tetrahedron 56, 3867–3874. Lee, Y.R., Kweon, H., Koh, W.S., Min, K.R., Kim, Y., Lee, S.H., 2001. One-pot preparation of pyranoquinolinones by ytterbium(III) trifluoromethanesulfonate-catalyzed reactions: efficient synthesis of Flindersine, N-Methylflindersine, and zanthosimuline natural products. Synthesis 12, 1851–1855. Lei, M., Hu, L., Ma, L., 2011. A green, efficient, and rapid procedure for the synthesis of 2-amino-3-cyano-1,4,5,6-tetrahydropyrano[3,2c]quinolin-5-one derivatives catalyzed by ammonium acetate. Tetrahedron Lett. 52 (20), 2597–2600. Magesh, C.J., Makesh, S.V., Perumal, P.T., 2004. Highly diastereoselective inverse electron demand (IED) Diels–Alder reaction mediated by chiral salen–AlCl complex: the first, target-oriented synthesis of pyranoquinolines as potential antibacterial agents. Bioorg. Med. Chem. Lett. 14 (9), 2035–2040. Manske, R.H.F., Rodrigo, R.G.A., 1988. In: The Alkaloids, vol. XVII. Academic Press, London, p. 105. Michael, J.P., 2002. Quinoline, quinazoline and acridone alkaloids. Nat. Prod. Rep. 19 (6), 742–760. Michael, J.P., 2003. Quinoline, quinazoline and acridone alkaloids. Nat. Prod. Rep. 20 (5), 476–493. Michael, J.P., 2004. Quinoline, quinazoline and acridone alkaloids. Nat. Prod. Rep. 21 (5), 650–668. Michael, J.P., 2005. Quinoline, quinazoline and acridone alkaloids. Nat. Prod. Rep. 22 (5), 627–646. Mondal, S., Paira, R., Maity, A., Naskar, S., Sahu, K.B., Hazra, A., Saha, P., Banerjee, S., Mondal, N.B., 2011. Basic alumina supported tandem synthesis of bridged polycyclic quinolino/ isoquinolinooxazocines under microwave irradiation. Tetrahedron Lett. 52, 4697–4700. Mulwad, V.V., Hegde, A.S., Suryanarayan, V., 1999. Reaction of hydroxycoumarins and its analogues. Indian J. Chem., Sect. B: Org. Chem. Incl. Med. Chem. 38, 148–151. Nahas, N.M., Abdel-Hafez, A.A., 2005. Synthesis and antibacterial activities of fused pyranoquinoline derivatives. Heterocycl. Commun. 11 (3–4), 263–272. Nasseri, M.A., Sadeghzadeh, S.M., 2013. A highly active FeNi3–SiO2 magnetic nanoparticles catalyst for the preparation of 4Hbenzo[b]pyrans and spirooxindoles under mild conditions. J. Iran. Chem. Soc. 10 (5), 1047–1056. Neve, J.E., Wijesekera, H.P., Duffy, S., Jenkins, I.D., Ripper, J., Teague, S.J., Quinn, R.J., 2014. Euodenine A: a small molecule agonist of human TLR4. J. Med. Chem. 57 (4), 1252–1275. Neville, C.F., Grundon, M.F., Ramachandran, V.N., Reisch, G., Reisch, J., 1991. Quinoline alkaloids. Part 28. The biosynthesis of furoquinolines and other hemiterpenoids in Ptelea trifoliata. J. Chem. Soc. Perkin Trans. 1 (9), 2261–2268. Ngadjui, B.T., Ayafor, J.F., Bilon, A.E., Sondengam, B.L., Connolly, J.D., Rycroft, D.S., 1992. Synthesis of veprisine dimers and the
M.M. Abdou formation of a novel cyclic tetramer from precocene I. Tetrahedron 48 (40), 8711–8724. No¨hammer, G., Kappe, T., 1976. Zur Reaktion von 4-Hydroxy-2chinolon mit reaktiven Malonsa¨urederivaten. Monatsh. Chem. 107 (4), 859–863. Pandey, G., Muralikrishna, C., Bhalerao, U.T., 1989. Mushroom tyrosinase catalysed synthesis of coumestans, benzofuran derivatives and related heterocyclic compounds. Tetrahedron 45, 6867–6874. Peng, Y., Song, G., Huang, F., 2005. Tetramethylguanidine[bmim][BF4]. An efficient and recyclable catalytic system for onepot synthesis of 4H-pyrans. Monatsh. Chem. 136 (5), 727–731. Rao, V.S., Darbarwar, M., 1989. A facile synthesis of 2-methyl-4-oxo4,5-dihydrofuro[3,2-] quinolines. Synthesis 1989 (2), 139–141. Ruano, J.L.G., Pedregal, C., Rodriguez, J.H., 1991. Synthesis and tautomerism of 2,4-dihydroxyquinolines. Heterocycles 32, 2151– 2159. Sainsbury, M., 1978. In: Coffey, S. (Ed.), . In: Rodd’s Chemistry of Carbon Compounds, vol. IVG. Elsevier, New York, p. 171. Sangeetha, V., Prasad, K.J.Rajendra, 2006. Synthesis of 12,13-dihydro-5-oxoquinolino[2,3-a]carbazoles, 3,11-dihydro-2,4-dioxopyrano[2,3-a]carbazoles and quinolino[2,3-b]carbazolo[6,5-a]pyran7,8-diones. Indian J. Chem., Sect. B: Org. Chem. Incl. Med. Chem. 45, 1487–1491. Schiemann, K., Emde, U., Schlueter, T., Saal, C., Maiwald, M. 2007. Preparation of polymorphic forms of pyranoquinolines for treatment of proliferative diseases. Int. Patent WO, 2007147480, A2, Chem. Abstr. 2007, 148, 85962. Schmidt, H.W., Junek, H., 1978. Cyclisierungsreaktionen zu Pyrano [3,2-c] pyridinen und pyrano [3,2-c] chinolinen unter Verwendung von Ethoxymethylen-malodinitril bzw.-cyanessigester Synthesen mit Nitrilen, 50. Mitt. pyrano [3,2-c] quinolines with ethoxymethylene-malonitrile and-ethyl cyanoacetate, resp. Monatsh. Chem. 109 (5), 1075–1080. Senboku, H., Takashima, M., Suzuki, M., Kobayashi, K., Suginome, H., 1996. Photoinduced molecular transformations. Part 159. Formation of some furonaphthyridinones by selective b-scission of cyclobutanoxyl radicals generated from [2+2] photoadducts of 4-hydroxy-1-phenyl [1,8] naphthyridin-2(1H)-one with alkenes. Tetrahedron 52 (17), 6125–6138. Shobana, N., Shanmugam, P., 1986. Sodium hydrogen telluride – a new convenient reagent for deblocking allyl carboxylates and allyl phenyl ethers. Indian J. Chem., Sect. B: Org. Chem. Incl. Med. Chem. 25 (6), 658-658. Shobana, N., Amirthavalli, M., Deepa, V., Shanmugam, P., 1988. Sodium hydrogen telluride- an efficient reagent for deblocking of aryl ethyl carbonates. Indian J. Chem., Sect. B: Org. Chem. Incl. Med. Chem. 27, 965–966. Sowellim, S.I.A., EI-Taweel, F.M.A., Elagamey, A., 1995. Cyclization reactions of a, b-unsaturated nitriles with quinoline and cinnoline derivatives: new approaches for synthesis of 4H-pyrano[3,2-c]quinoline and 4H-pyrano[3,2-c]cinnoline derivatives. Egypt. J. Chem. 38, 511. Sowellim, S.Z.A., El-Taweel, F.M.A.A., Elagamey, A.G.A., 1996. Activated nitriles in organic synthesis: synthesis of pyranoquinolinone, 6H-2-benzopyrano[4,3-c]quinolinone and thieno[2,3-b]pyridine. Bull. Soc. Chim. Fr. 133, 229–234. Subramanian, M., Mohan, P.S., Shanmugam, P., Prasad, K.J., Rajendra, Z., 1992. Quinoline alkaloids. Synthesis of khaplofoline, ribalinine, and flindersine. Naturforsch. B 47 (7), 1016–1020. Suginome, H., Kobayashi, K., Itoh, M., Seko, S., Furusaki, A., 1990. Photoinduced molecular transformations. 110. Formation of furoquinolinones via .beta.-scission of cyclobutanoxyl radicals generated from [2 + 2] photoadducts of 4-hydroxy-2-quinolone and acyclic and cyclic alkenes. X-ray crystal structure of (6a.alpha., 6b.beta., 10a.beta., 10b.alpha.)-(+)-10b-acetoxy-6a,6b,7,8,9,10, 10a,10b-octa hydro-5-methylbenzo[3,4]cyclobuta[1,2-c]quinolin6(5H)-one. J. Org. Chem. 55 (16), 4933–4943.
Please cite this article in press as: Abdou, M.M. Chemistry of 4-hydroxy-2(1H)-quinolone. Part 2. As synthons in heterocyclic synthesis. Arabian Journal of Chemistry (2014), http://dx.doi.org/10.1016/j.arabjc.2014.11.021
Chemistry of 4-hydroxy-2(1H)-quinolone Suginome, H., Seko, S., Konishi, A., Kobayashi, K., 1991. One-step formation of furo [3, 2-c] quinolin-4 (5H)-ones by a new regioselective [2+3] photoaddition of methoxy-substituted 4-hydroxyquinolin-2-one with alkenes1. Tetrahedron Lett. 32 (38), 5115–5118. Suresh, T., Dhanabal, T., Nandha Kumar, R., Mohan, P.S., 2005. Synthesis of pyranoquinoline alkaloids via (4+2) cycloaddition reaction. Heterocycl. Commun. 11, 79–84. Svoboda, G.H., Poore, G.A., Simpson, P.J., Boder, G.B., 1966. Alkaloids of Acronychia Baueri Schott I: isolation of the alkaloids and a study of the antitumor and other biological properties of acronycine. J. Pharm. Sci. 55 (8), 758–768. Tabakovic, I., Grujic, Z., Bejtovic, Z., 1983. Electrochemical synthesis of heterocyclic compounds. XII. Anodic oxidation of catechol in the presence of nucleophiles. J. Heterocycl. Chem. 20, 635–638. Thangavel, D., Ravindran, S., Moonsamy, G.R., Palathurai, M.S., 2007. Simple efficient synthesis of pyranoquinoline alkaloids: flindersine, khaplofoline, haplamine and their analogues. J. Chem. Res., Synop. 2, 124–126. Ukrainets, I.V., Sidorenko, L.V., Gorokhova, O.V., Slobodzyan, S.V., 2006. 4-Hydroxy-2-quinolones. 97. Simple synthesis of the esters of 4-halo-substituted 2-oxo-1,2-dihydroquinoline-3-carboxylic acids. Chem. Heterocycl. Compd. 42 (7), 882–885. Wabo, H.K., Tane, P., Connolly, J.D., Okunji, C.C., Schuster, B.M., Iwu, M.M., 2005. Tabouensinium chloride, a novel quaternary pyranoquinoline alkaloid from Araliopsis tabouensis. Nat. Prod. Res. 19 (6), 591–595. Wang, X., Yong, R.L., 2007. Efficient synthesis of substituted pyranoquinolinones from 2,4-dihydroxyquinoline: total synthesis
11 of zanthosimuline, cis-30 ,40 -dihydroxy-30 ,40 -dihydroflindersine, and orixalone. Synthesis 19, 3044–3050. Wang, X.S., Zeng, Z.S., Shi, D.Q., Tu, S.J., Wei, X.Y., Zong, Z.M., 2004a. Study on the reaction of arylmethylidenemalononitriles with 4-hydroxy-1,2-dihydroquinolin-2-one. Chin. J. Org. Chem. 24 (12), 1595–1597. Wang, X., Zeng, Z., Shi, D., Wei, X., Zong, Z., 2004b. One-step synthesis of 2-amino-3-cyano-4-aryl-1,4,5,6-tetrahydropyrano[3,2c]quinolin-5-one derivatives using KF-Al2O3 as catalyst. Synth. Commun. 34, 3021–3027. Wang, X.S., Zhang, M.M., Zeng, Z.S., Shi, D.Q., Tu, S.J., Wei, X.Y., Zong, Z.M., 2005. A Clean procedure for the synthesis of chromeno[4,3-b]benzo[f]quinoline and quinolino[4,3-b]benzo[f] quinoline derivatives in aqueous media. Chem. Lett. 34 (10), 1316–1317. Wang, X.S., Zeng, Z.S., Li, Y.L., Shi, D.Q., Tu, S.J., Wei, X.Y., Zong, Z.M., 2006. Synthesis of 2-amino-4-aryl-5, 6-dihydro-4H-pyrano [3,2-c] quinolin-5-one derivatives in water. Chin. J. Org. Chem. 26 (2), 228–232. Wolters, B., Eilert, U., 1981. Antimicrobial substances in callus cultures of Ruta graveolens. Planta Med. 43 (10), 166–174. Ye, J.H., Ling, K.Q., Zhang, Y., Li, N., Xu, J.H., 1999. Syntheses of 2-hydroxypyrano[3,2-c]quinolin-5-ones from 4-hydroxyquinolin2-ones by tandem Knoevenagel condensation with aldehyde and Michael addition of enamine with the quinone methide-thermoand photochemical approaches. J. Chem. Soc., Perkin Trans. 1 (14), 2017–2024.
Please cite this article in press as: Abdou, M.M. Chemistry of 4-hydroxy-2(1H)-quinolone. Part 2. As synthons in heterocyclic synthesis. Arabian Journal of Chemistry (2014), http://dx.doi.org/10.1016/j.arabjc.2014.11.021