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Arabian Journal of Chemistry (2014) xxx, xxx–xxx
King Saud University
Arabian Journal of Chemistry
www.ksu.edu.sawww.sciencedirect.com
REVIEW
Chemistry of 4-hydroxy-2(1H)-quinolone. Part 2.
As synthons in heterocyclic synthesis
* 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.2014.11.0211878-5352 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 C(2014), http://dx.doi.org/10.1016/j.arabjc.2014.11.021
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-hydroxy-
2(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. Introduction . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 002. Synthesis of fused heterocyclic compounds . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 00
2.1. [6-6-5] ring system. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 00
2.1.1. Dihydrofuran and furoquinolinones . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 002.2. [6-6-5] ring system. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 002.3. Fused [6-6-6] ring system. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 00
2.3.1. Quinolino[4,3-b]benzo[f]quinolin-6-one . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 002.3.2. Pyranoquinolines . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 002.3.3. Quinolinobenzothiazinones . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 00
2.4. [6-6-8-6] ring system . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 002.4.1. Oxazocines . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 00
3. Conclusion . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 00
hemistry
2 M.M. Abdou
Acknowledgements . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 00
References . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 00
1 2
NH
O
OH
+ OEtNH
O
OOEt
acetonitrile/ refluxAg2CO3 / Celite
3
Scheme 1
NH
O
OH
Ag (I)
Ag (0)NH
O
O.
NH
O
OOEt.
NH
O
OOEt+
NH
O
OOEt
+Ag (I)
Ag (0)
-H+
2
1 4 5
6 7
3
Scheme 2
1. Introduction
4-Hydroxy-2(1H)-quinolone is a versatile and convenientprecursor for the synthesis of a wide variety of heterocycliccompounds (Ghandi et al., 2013; Guo et al., 2013;
Abbaspour-Gilandeh et al., 2013; Neve et al., 2014; Hoeckerand Gademann, 2013). It is of particular interest as a verypromising reagent for cascade heterocyclization, which will
undoubtedly become one of the main approaches to thetargeted synthesis of heterocycles in the near future, in therapidly-rising field of combinatorial chemistry. This newmethodology based on automatic, high-tech synthetic methods
enables synthesis of a large number of novel organiccompounds 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-hydroxy-
2(1H)-quinolone chemistry.
In the literature survey, the reactions involving 4-hydroxy-
2(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.
2. Synthesis of fused heterocyclic compounds
2.1. [6-6-5] ring system
2.1.1. Dihydrofuran and furoquinolinones
Dihydrofuroquinolinone and furoquinolinone alkaloids arewidely distributed in nature (Subramanian et al., 1992;Shobana and Shanmugam, 1986; Shobana et al., 1988;
Ukrainets et al., 2006). They are primarily isolated fromRutaceae species as an angularly and linearly fused structure.They are reported to have various biological activities suchas antimicrobial, antimalarial, insecticidal, antineoplastic,
antidiuretic, antiarrhythmic and sedative (Wolters and Eilert,1981; Svoboda et al., 1966; Basco et al., 1994). This wide rangeof biological properties has stimulated interest in the synthesis
of dihydrofuroquinolinone and furoquinolinone derivatives.A number of synthetic approaches to dihydrofuroquinolinones
Please cite this article in press as: Abdou, M.M. Chemistry of 4-hydroxy-2(1H)-quino(2014), http://dx.doi.org/10.1016/j.arabjc.2014.11.021
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-centeredradicals 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 medi-ated by the oxidative cyclization of 4-hydroxy-2(1H)-quino-
lone 1 with ethyl vinyl ether 2 and silver(I)/Celite (Fetizonreagent) in acetonitrile under reflux (Scheme 1).
Although the exact mechanism of the reaction is not clearyet, it is best described as shown in Scheme 2. The starting
material 1 is first oxidized by one equivalent of Ag(I) to gener-ate the radical 4, which then attacks olefin 2 to give the radicaladduct 5. The adduct 5 now undergoes fast oxidation by
another one equivalent of Ag(I) to a carbocation 6. Cyclizationof the carbocation 6 furnishes intermediate 7, whose deproto-nation affords the product 3 (Scheme 2).
2.1.1.1.2. Using Ce(IV). There has been a considerableinterest 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-methylimida-zolium 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
lone. Part 2. As synthons in heterocyclic synthesis. Arabian Journal of Chemistry
NH
O
OH
CAN-[bmim][BF4]CH2Cl2 / 40o C
+
1 8
N OH
OPh
N O
OH
Ph
9 (42%) 10 (35%)
+
Scheme 3
Chemistry of 4-hydroxy-2(1H)-quinolone 3
1,1-diphenylethene 11 in boiling glacial acetic acid afforded3,5-dihydro-2H-furo[3,2-c]quinolin-4-one 12 (Kumabe andNishino, 2004) (Scheme 4).
Despite the uncertainty related to the reaction mechanism,the authors point toward manganese(III) that could oxidizetertiary carbon radical 14 to afford the corresponding carboca-tions 15, 16 which were converted into compound 12
(Scheme 5).
1
NH
O
O
NH
O
OH
+Mn(OAc)3
AcOH/100oC
PhPh
12 (73%)
Ph Ph
11
Scheme 4
NH
O
OH
Mn(OAc)3
AcOH, reflux NH
O
OMn(III)
NH
O
OPh Ph.
NH
O
OPh Ph+
NH
O
OPh Ph
+-H+
12Mn(OAc)3
AcOH, reflux
11
1 13 14
15 16
Scheme 5
NH
O
OH
R1
R2 Mn(OAc)3, 40oC[bmim][BF4]:CH2Cl2
1 17
+
17, 18, 19 R1 R
a Ph H
b Me P
c C3H7H
d C6H13 M
Scheme
Please cite this article in press as: Abdou, M.M. Chemistry of 4-hydroxy-2(1H)-quinol(2014), http://dx.doi.org/10.1016/j.arabjc.2014.11.021
A similar, manganese(III)-mediated reaction using 4-hydroxy-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).
2.2. [6-6-5] ring system
Laccase (Agaricus bisporus)-catalyzed domino reaction of 4-hydroxy-2(1H)-quinolone 1 with catechols 20 using aerial oxy-gen as the oxidant delivers for the synthesis of 10-substituted
8,9-dihydroxybenzofuro[3,2-c]quinolin-6(5H)-ones 21 as singleregioisomers with yields ranging from 61% to 77% (Hajdoket al., 2009) (Scheme 7). Some of these compounds have been
made accessible by other methods, including tyrosinase-cata-lyzed oxidation, electrochemical oxidation or crude peroxidase
R1
N OH
OR2
R1
R2N O
OH
18 19
+
2Yield% (18/19)
41/39
h 41/34
71/8
e 41/4
6
OH
NH
O
O
R
OH
ONH
OH R
OH
OH+
pH=6.0, r.t.
1 20 21
cat. laccase, O2
20, 21 R t/h Yield %
a H 20 73
b Me 18 77
c OMe 20 61
Scheme 7
one. Part 2. As synthons in heterocyclic synthesis. Arabian Journal of Chemistry
OH
OHoxidation
-2e, -2H
O
O
ONH
OH
1
__
O
O
1,4-addition
ONH
OHOH
OH
1,4-additionoxidation
-2e, -2H ONH
OHO
O
__ OH
NH
O
O
OH
25
20a 22
22 23
24
Scheme 8
1 33 34
+
NH
O
OH
OMeO
N HN R
NH
O
O
O HN R
O
OAcOH
R= OMe, Ph
Scheme 11
4 M.M. Abdou
from onion solid waste (Pandey et al., 1989; Tabakovic et al.,1983; Angeleska et al., 2013).
The reaction is postulated to proceed through a dominoprocess involving several steps (Scheme 8). Initially, thelaccase-catalyzed oxidation of the catechol 20 with O2 to
NH
O
OH
N
1
+
26
26, 27 a b c dAr 2-Cl 4-Cl 3,4-Cl2 2,4-C
Time/ h 8 8 8 8
Yield % 94.2 90.2 93.2 97.
Scheme
NH
O
OH
1
+NPh
NH
O
OH
OH
Ph
NH
O
HN
Ph
HO
26
29
30
32
Scheme 1
Please cite this article in press as: Abdou, M.M. Chemistry of 4-hydroxy-2(1H)-quino(2014), http://dx.doi.org/10.1016/j.arabjc.2014.11.021
benzoquinone 22, which then undergoes an intermolecular1,4-addition with the enol of 1 as a nucleophile to yield 23.
A second laccase-catalyzed oxidation to the quinone interme-diate (24) which further undergoes an intramolecular 1,4-addi-tion to produce the final tetracyclic heterocycles.
2.3. Fused [6-6-6] ring system
2.3.1. Quinolino[4,3-b]benzo[f]quinolin-6-one
A short and simple synthesis of quinolino[4,3-b]benzo[f]quino-line derivatives 27 was accomplished in high yields via the
NH
O
HNR
R27
TEBACH2Ol100 oC
e f g hl2 4-F 4-Br 4-CH3 3-Cl
8 10 12 10
0 92.5 93.5 91.6 87.8
9
NH
O
OH
NH
PhH2O
NH2
NH
O
OH2N
-H2O
NH
O
HN
Ph
28
31
27
0
lone. Part 2. As synthons in heterocyclic synthesis. Arabian Journal of Chemistry
NH
OH
O ONH
OHR
O
NH
O
OR
OO
HN
EtO
OEt
OEt Ac2O
1
+ + 90°C, 4 h
35 7363
35,37 R Yield %
a Ph 71
b Me 46
c 2-Pyrazinyl 9
d 3-Pyridinyl 31
Scheme 12
NH
OH
O
1
+NH
O
O
O HN Ph
O
O
NEtO
Ph
O
NEt3, pyridine
Reflux, 4h
39 (69%)38
Scheme 13
NH
O
OH
+NH
O
O
O
O
OEt
O
Pyridine, DMFHeating, 5h
OO
41 (58 %)1 40
Scheme 14
NH
O
OH
+NH
O
O
REtO
CN
OR
NaOEt, EtOH
R: CN, COOEt.
1 3424
Scheme 15
NH
O
OH
+ OEtEtO
OO
O
CH3CO2N
0.5h
1 44
Scheme 1
Chemistry of 4-hydroxy-2(1H)-quinolone 5
Please cite this article in press as: Abdou, M.M. Chemistry of 4-hydroxy-2(1H)-quinol(2014), http://dx.doi.org/10.1016/j.arabjc.2014.11.021
reaction of N-benzilidenenaphthalen-2-amines 26 and 4-hydroxy-2(1H)-quinolone 1 in aqueous media catalyzed by tri-ethylbenzylammonium chloride (TEBAC) (Wang et al., 2005)(Scheme 9).
Though the detailed mechanism of the above reaction hasnot been clarified yet, the formation of 27 can be explainedby the possible mechanism presented in Scheme 10.
2.3.2. Pyranoquinolines
Pyranoquinolines are the main constituent unit of the many ofthe alkaloids of the plant family Rutaceae (Manske and
Rodrigo, 1988; Sainsbury, 1978; Chen et al., 1997; Waboet al., 2005; Michael, 2002, 2003, 2004, 2005) and have gainedmuch importance because of their interesting pharmacological
properties and synthetic applications (Chen et al., 1994; Barret 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[3,2-c]quinoline-2,5(2H,6H)-diones. Many methods for the synthe-sis of pyrano[3,2-c]quinoline-2,5(2H,6H)-dione derivatives
have been reported successively. It has been reported thatthe preparation of 3-acetyl(benzoyl)amino-5,6-dihydropyr-ano[3,2-c]quinoline-2,5(2H,6H)-dione 34 was accomplished
by the treatment of methyl 2-acetyl(benzoyl)amino-3-(N,N-dimethylamino)propenoates 33 with 1 in acetic acid (Ngadjuiet al., 1992; Kralj et al., 1997) (Scheme 11).
An elegant and efficient one-pot synthesis of acylaminoderivatives of quinoline 37 was achieved by the reaction of35, triethyl orthoformate (TOF) 36 and 4-hydroxy-2(1H)-quin-olone 1 in acetic anhydride (Kmetic et al., 1993) (Scheme 12).
Kepe et al. (1995) observed that treatment of 4-ethoxymeth-ylene-2-phenyl-5(4H)-oxazolone 38 with 1 under basicconditions in boiling mixtures of pyridine and triethylamine
NH
O
O
O
COOEtH4, nitrobenzene
, 220 °C
45
6
one. Part 2. As synthons in heterocyclic synthesis. Arabian Journal of Chemistry
NH
O
OH
NH
O
O
O
R1
R2
EtO
OO
R2R1
CH3COONH4, nitrobenzene+
200 °C
1 46 47
46, 47 R1 R2 Yield %
a H CH3 73 %
b H C6H5 47 %
c CH2-C6H5 CH3 83 %
Scheme 17
NH
OH
O NH
O
OR2
NH2
R2
CNH
R1
R1
+ reflux
A : Triethylamine in ethanol, Time= 0.75h, Heating.B : Piperidine in ethanol, Time= 2h, Heating.
1 48 49
A,B
48,49 R1 R2Yield%(A/B)
a H CN 83/ 70
b 4-N(CH3)2 CN --/ 63
c 4-OCH3 CN --/ 65
d 4-Cl CN 79/ 60
e H COOEt 87 / 67
f 4-CH3 COOEt 90 / --
g 4-OCH3 COOEt 63 / --
h 4-Cl COOEt 84 / 65
Scheme 18
R_CHO +CN
CN NH4OAC CNR
CN
1
NH
O
OH
NH4OAC_H
54
NH
O
O
53
NH
NCO
R
O
CN
NH
O
R
O
CNN
NH4OAC
NH
O
R
O
CNNH
NH
O
R
O
CNNH2
50 51 53
55
565752
Scheme 20
6 M.M. Abdou
led to N-(5,6-dihydro-2,5-dioxo-2H-pyrano[3,2-clquinoline-3-yl)benzamide 39 [50] (Scheme 13).
4-Hydroxy-2(1H)-quinolone 1 when condensed with ethyl-2,3-dihydro-3-oxobenzofuran-2-carboxylate 40 afforded thecorresponding 6H,12H-benzofuropyrano[3,2-c]quinoline-6,12-
diones 41 (Kepe et al., 1992) (Scheme 14).
R : CH3CH2, CH3CH2CH2, C6H5, 4-CH3C6H4, 4- 4-NO2C6H4, 4-CNC6H4, 4-ClC6H4 , 4-BrC6H 3,4-OCH2OC6H3, 3- CH3O-4-HOC6H3, 2-Fur
501
CN
CNR-CHO +
NH
O
OH
+
51
Scheme 1
Please cite this article in press as: Abdou, M.M. Chemistry of 4-hydroxy-2(1H)-quino(2014), http://dx.doi.org/10.1016/j.arabjc.2014.11.021
Reaction of ethoxymethylenemalononitrile and ethylethoxymethylenecyanoacetate 42, with 4-hydroxy-2(1H)-quin-
olone 1 led to the corresponding 2,5-dioxo-5,6-dihydro-pyr-ano[3.2-c]quinolines 43 exhibiting remarkable visible fluo-rescence (Mulwad et al., 1999) (Scheme 15).
Schmidt and Junek (1978) have reported the synthesis ofpyrano[3,2-c]quinoline-2,5-diones 45 via the treatment of4-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
CH3OC6H4, 4-FC6H4, 4-HOC6H4, 2-ClC6H4,4,3-NO2C6H4 , 2,4-Cl2C6H3 , 3,4-Cl2C6H3 ,yl, 4-Pyridyl.
NH
O
R
O
CNNH2
52
EtOH
9
lone. Part 2. As synthons in heterocyclic synthesis. Arabian Journal of Chemistry
1 58 59
NH
O
OH
+ +NH
O
O
60 (82 %)
(CH2O)n
COOH1,4-dioxaneN2 atm, 4.5 h
Scheme 21
NH
OH
O
1
+NH
OCH3CHO
Et2NH, C6H6Heating, 5h
O
OH
62 (51%)61
Scheme 22
1
NH
NH
O
OO
OH
+
69 (67%)
PPA, xylene10h, 145 °C
68
Scheme 24
NH
O
OH
NH
O
O
H3C R
RO+
Conditions: A : Yb(OTf)3, CH3CN, 12h, Heating. B : Ethylenediaminediacetic acid in CH2Cl2, Time= 10h, T= 20 °C.
C: Water, 6h, 80 °C.
Variousconditions
1 70 71
70,71 R Condition Yield %
a H A 53
a H B 70
b CH3 A 50
b CH3 C 70
b CH3 B 94
c C2H5 B 77
d C3H7 B 82
e CH2-CH2=CH-CH(CH3)2 A 40
f CH2-CH2=CH-CH(CH3)2 C 71
Scheme 25
NH
O
OH
+O
OH
HN
O
+Cl
ClO
O
RO
RN toluene
80-95 0C
R= C6H5, CH2C6H5
1 72 73 74
Scheme 26
Chemistry of 4-hydroxy-2(1H)-quinolone 7
ammonium acetate at 200 �C in nitrobenzene (Scheme 17).
Also, this reaction can be performed in pyridine instead ofnitrobenzene.
2.3.2.1.2. 2-Aminopyrano[3,2-c]quinolin-5-ones.
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 thepresence of base (triethylamine or piperidine) as a catalyst
resulting in the corresponding 2-amino-4-aryl-1,4,5,6-tetrahy-dro-pyrano[3,2-c]quinolin-5-ones 49 (Scheme 18).
Using three component condensation: There have been severalmethods for synthesizing pyranoquinoline derivatives, includ-ing the three-component reaction of 4-hydroxy-2(1H)-quino-
lone 1, aldehydes 50, malononitrile for the synthesis of2-amino-3-cyano-1,4,5,6-tetrahydropyrano[3,2-c]quinolin-5-onederivatives 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) (Sowellimet 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.
1
NH
O
OH
_HDEA
63
NH
O
O
CH3CHO
64NH
O
O OH
65
NH
O
O
66
NH
O
OH
NH
O
CH3 OH
-H2O
RCH=CHNEt2
NH
O
O
NEtEt
NH
O
O
OH
hydrolysis
67
H
H, 63
62
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
NH
O
OH
+1 h
O
O
OHN
NaOHO
O
HNCH3
HN
O
OO
+
H3C
1 75 76 77
Scheme 27
1 7978
NH
O
OH
+NH2
SH
NH
O
SHN
.DMF
120 °C, 12h
Scheme 28
8 M.M. Abdou
(2013) found that 2-amino-3-cyano-1,4,5,6-tetrahydropyr-
ano[3,2-c]quinolin-5-one derivatives 52 could be preparedwithout catalyst in a mixed solvent of ethanol and water.
The condensation of 1, aldehyde 50, malononitrile 51 mayoccur by a mechanism of Knoevenagel condensation, Michaeladdition, intramolecular cyclization, and isomerization. Ini-
tially, intermediate 53 is formed by Knoevenagel condensationof aldehyde 50 and malononitrile 51 by the action ofammonium acetate. Then, the proton of 4-hydroxy-2(1H)-
quinolone 1 is abstracted by ammonium acetate to formintermediate 54. Michael addition of intermediate 54 on 53
leads to the formation of 55, followed by cyclization andisomerization, affords the corresponding 2-amino-4H-pyr-
ano[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 wasprepared by refluxing a solution of l with para-formaldehyde 58
and 3,3-dimethylacrylic acid 59 in 1,4-dioxane under nitrogenatmosphere for 4.5 h (Suresh et al., 2005) (Scheme 21).
2,3,4,6-Tetrahydro-2-hydroxy-4-methylpyrano[3,2-c]quino-
lin-5-one 62 are synthesized from 4-hydroxy-2(1H)-quinolone
3
2
1
1 2
3
3
3 3
3 3
Scheme 2
Please cite this article in press as: Abdou, M.M. Chemistry of 4-hydroxy-2(1H)-quino(2014), http://dx.doi.org/10.1016/j.arabjc.2014.11.021
1 by tandem Knoevenagel condensation with an acetaldehyde61 in the presence of diethylamine as a base in refluxingbenzene (Ye et al., 1999) (Scheme 22).
The possible mechanism could account for the formation ofproduct 62 via base-catalyzed condensation of a quinolinone 1with an acetaldehyde 61 yielding the corresponding 4-hydroxy-
3-(1-hydroxyethyl)quinolin-2-one 64, which is dehydrated onheating in the basic reaction medium to furnish the highlyelectrophilic quinone methide intermediate 65. The quinonemethide 65 then undergoes competitive Michael-type addition
of the enamine proceeds in a 1,4-fashion and results in anintramolecular 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 iso-
prene 68 with 4-hydroxy-2(1H)-quinolone 1 in the presence ofpolyphosphoric acid, furnishing dihydroflindersine 69 in goodyield (Scheme 24).
2.3.2.1.4. Miscellaneous pyrono quinolone. In water medium,
environmentally benign, facile, and efficient synthesis of pyr-ans 71 was achieved in good yields by domino Knoevenagelreaction of 1 with several a,b-unsaturated aldehydes 70 (Jung
et al., 2010) (Scheme 25). This method has been successfullyapplied to the synthesis of biologically interesting and natu-rally occurring pyranoquinolinone alkaloids in good yields.
Also, this reaction can be achieved by ytterbium(III) triflate(Lee et al., 2001) or ethylenediaminediacetic acid in dichloro-methane (Wang and Yong, 2007).
2.3.2.3. Linear pyranoquinolines. Nohammer and Kappe (1976)showed that the reaction of 4-hydroxy-2(1H)-quinolone 1 withmalonyl chlorides 72 in the presence of N,N-dimethylaniline 73
31
2
9
lone. Part 2. As synthons in heterocyclic synthesis. Arabian Journal of Chemistry
Chemistry of 4-hydroxy-2(1H)-quinolone 9
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]carbaz-olo[6,5-a]pyran-7,8-diones 77 with interesting biological activ-ity via reaction of 1 with vinyl acetate 75 and 3,11-dihydro-2,4-
dioxopyrano[2,3-o]carbazoles 76 (Scheme 27).
2.3.3. Quinolinobenzothiazinones
One of the most successful strategies for constructing 5H-quin-
olin[3,4-b][1,4]benzothiazin-6(12H)-one 79 as a new agent withestrogenic activity mediated by estrogen receptors (ER) is thecondensation 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 (Coppolaet al., 1981) (Scheme 28).
2.4. [6-6-8-6] ring system
2.4.1. Oxazocines
Basic alumina supported and solvent-free synthesis of noveloxazocines 81 has been achieved in excellent yields by tandemC-alkylation followed by intramolecular O-alkylation of 1 with
quinolinium salts 80 under microwave irradiation (Mondalet al., 2011) (Scheme 29).
3. Conclusion
The data considered in this review clearly demonstrate that 4-hydroxy-2(1H)-quinolone may be successfully used to synthe-
size a wide variety of heterocycles of academic and pharmaceu-ticals interest. Finally, all chemistry presented here along withthat 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 myco-workers mentioned in the list of references. For financial
support, I would like to thank the Academy of ScientificResearch and Technology, ASRT, Egypt. Also, the authorregrets any omissions that may have occurred in this review.
Finally, I would like to thank Professor El-Sayed I. El-Desokyfor reading the manuscript and making useful suggestions.
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