Diversity-oriented Multicomponent Synthesis of Bisquinolones under Green Conditions

Article abstract of DOI:10.1002/jhet.2994

A diversity-oriented green and eco-friendly synthesis of bisquinolones have been developed by simply condensation of N-methylquinolone (1), with various benzaldehydes 2a–n and aniline (3) under catalyst-free conditions. An exciting feature of this communication is the product formation that depends on the intermediate (II) generated in the reaction mechanism.

Full text of DOI:10.1002/jhet.2994

Month 2017
Diversity-oriented Multicomponent Synthesis of Bisquinolones under
Green Conditions
Madhu Bandia,b
and Ch.Venkata Ramana Reddyb
*
aJawaharlal Nehru Technological University, Kakinada, AP, India
bDepartment of Chemistry, Jawaharlal Nehru Technological University Hyderabad College of Engineering, Kukatpally,
Hyderabad, TS 500 085, India
*
E-mail: madhubandi2@gmail.com
Received April 28, 2017
DOI 10.1002/jhet.2994
Published online 00 Month 2017 in Wiley Online Library (wileyonlinelibrary.com).
A diversity-oriented green and eco-friendly synthesis of bisquinolones have been developed by simply
condensation of N-methylquinolone (1), with various benzaldehydes 2a–n and aniline (3) under catalyst-
free conditions. An exciting feature of this communication is the product formation that depends on the
intermediate (II) generated in the reaction mechanism.
J. Heterocyclic Chem., 00, 00 (2017).
INTRODUCTION
methods have been developed for the preparation of 3
and 4-substituted quinoline derivatives [13], and because
of their biological importance as substructures in a broad
range of designed and natural products [14], significant
efforts continue to be directed into the development of
new quinoline-based structures and new methods for their
construction. Many of the biologically important
quinolines and its derivatives can easily be synthesized
from readily available chemicals with the help of multi-
component reactions [15]. These reactions are allowed for
rapid synthesis of biologically active compound libraries
by combining three or more reagents into a single
product in one step.
Among the all nitrogen-containing and oxygen-
containing heterocycles, quinolines and quinolones are
the common core skeletons of some potent
pharmaceutical drugs [1] and biologically active alkaloids
[2]. These derivatives are important class of organic and
biomolecules that attract the interest of both synthetic and
medicinal researchers. Some of the functionalized
quinolines [3] have found applications as pharmaceuticals
and agrochemicals [4] as well as useful synthetic blocks
in the preparation of several natural products [5].
Especially quinoline-containing drugs are found in a
verity of biologically active compounds and are widely
used in the treatment of malaria [6], and some of the
quinoline-based drugs act as antibacterial [7], antiviral
[8], antifungal [9], anti-malarial [10], and anti-
inflammatory [11] agents. In addition, because of their
medicinal applications, quinolines and quinolone
derivatives have been employed in the study of
bioorganic and bioorgano-metallic process [12]. Several
© 2017 Wiley Periodicals, Inc.

M. Bandi and C. V. R. Reddy
Vol 000
Scheme 1. Multi-component reaction of 1 with 2a–n and 3 in water. [Color figure can be viewed at wileyonlinelibrary.com]
The naphthyridine [16] and acridine [17] derivatives are
an important class of nitrogen heterocycles that can be
converted into biologically active compounds exhibiting
variety of biological and pharmaceutical properties, such
as anti-tumor [18], anti-cancer [19], anti-malarial [20],
anti-multidrug-resistant [21], fungicidal [22], and
cytotoxic [23] properties, and are widely prescribed as
calcium bêta-blockers. In addition to their important
pharmacological properties, these derivatives are used as
dyes, fluorescent materials for visualization of bioactive
molecules, and in laser technology because of their useful
spectroscopic properties. The synthesis of naphthyridine
analogues related to the anti-malarial natural product
dependents would allow for an interesting analysis of the
relationship between the two heterocyclic systems and
their biological effects. In view of the broad utility
of naphthyridine and acridine derivatives, the synthesis of
this class of compounds under green conditions is of
paramount importance in synthetic organic chemistry
[24]. The multi-component condensation of 1,3-dione-
like compounds, aromatic aldehydes, and anilines by
heating in organic solvent or under microwave irradiation
has recently emerged as a potential route for the synthesis
of structurally divers naphthyridine and acridine
molecules. Few catalytic methods are available in
literature, which deals with the synthesis of these
molecules via multi-component route. Recently, Hivani
et al. [25] reported one-pot three-component synthesis of
novel acridine-5,6-diones from naphthoquinone under
PTSA condition. Li et al. [26] reported ionic liquid-
mediated one-pot synthesis of acridine-1,6-diones from
2-hydroxy naphthoquinone at room temperature. Javad
et al. [27] reported ZnO nanoparticle-catalyzed synthesis
of acridine derivatives from 1,3-dione under solvent-free
condition.
According to the literature mentioned previously, the
multi-component reaction of 1,3-diones or active
hydroxyl compounds with aromatic aldehydes and
anilines gave either naphthyridine or acridine derivatives
are the desired products. In this paper, our study began
with the multi-component reaction of 4-hydroxy-1-
methylquinolin-2(1H)-one [28] with aniline and different
aromatic aldehydes under green conditions.
RESULTS AND DISCUSSION
As illustrated in Scheme 1, the first experiment was
carried out in water at a room temperature, and
Table 1
Effect of solvent and temperature on formation of 6a.
Temp
(°C)
Time
(min)
Yield
(6a)
Yield
(7a)
Entry
Solvent
Water
1
2
3
4
5
RT
Reflux
RT
Reflux
Reflux
120
60
120
60
—
91
—
80
86
—
—
90
15
Trace
Water
Acetic acid
Acetic acid
Ethylene
glycol
60
6
7
8
9
10
11
12
Glycerol
PEG-600
DMF
Acetonitrile
THF
Methanol
Solvent-
free
Reflux
Reflux
Reflux
Reflux
Reflux
Reflux
100
60
60
60
60
60
60
15
82
85
70
68
68
74
30
Trace
Trace
Trace
Trace
Trace
Trace
Trace
Journal of Heterocyclic Chemistry
DOI 10.1002/jhet

Month 2017
Diversity-oriented Multicomponent Synthesis of Bisquinolones under
Green Conditions
4-hydroxy-1-methylquinolin-2(1H)-one (1), benzaldehyde
(2a), and aniline (3) were chosen as model reaction;
there is no product formation obtained, but the reaction
mixture was refluxed for 2–3 h till the reaction was
complete (checked by TLC) and once the main
product was purified, and the structural elucidation of
the isolated substance revealed surprisingly that
instead of the desired molecules 5-methyl-7-phenyl-
7,12-dihydrodibenzo[b,h][1,6]naphthyridin-6(5H)-one
(4a) and 4-hydroxy-1-methyl-3-(phenyl(phenylamino)
methyl)quinolin-2(1H)-one (5a),
a
new compound
6a with the 3,30-(phenylmethylene)bis(4-hydroxy-1-
methylquinolin-2(1H)-one) was obtained as a single
product and in good yield. The structure of the 6a was
Scheme 2. Effect of solvent and catalyst on formation of 6a–n and 7a–n.
Scheme 3. Plausible mechanism for synthesis of 6.
Journal of Heterocyclic Chemistry
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M. Bandi and C. V. R. Reddy
Vol 000
established based on its spectral properties (IR, 1H-
NMR, mass). Thus, its IR (KBr) spectrum showed a
very broad absorption at 2970 cmꢀ1 due to the
presence of the hydroxyl groups and a strong, sharp
absorption at 1627 cmꢀ1 due to the amide carbonyl
groups. Its H-NMR, in DMSO-d6, showed peaks at δ
1
3.72 (s, 6H, 2X–CH3, 6.28 (s, 1H, ꢀCH–Ar), 7.06–
8.07 (m, 13H, eight aryl protons of quinoline rings plus
five protons of the phenyl ring), 12.60 (s, 2H, ꢀOH,
D2O exchangeable). Its LC-MS spectrum, when
recorded in the Q + 1 mode, showed the molecular
ion peak at m/z 439 corresponding to a molecular
mass of 438.
The reaction conditions were varied (Table 1), in order to
improve the yield and to establish a green method for the
selective preparation of product 6a, and all the
experiments gave good-to-excellent yield in green solvents
and moderate yield in organic solvents. But when the
reaction was carried out in acetic acid at room
temperature, Schiff’s base (7a) was found as single
product instead of 6a (Scheme 2). But the same reaction
Table 2
Effect of Lewis acid catalysts on formation of 6a.
Temp
(°C)
Yield
(%) (6a) (%) (7a)
Yield
Entry
Catalyst
Solvent
1
2
3
4
5
6
7
No catalyst Water
Reflux
Reflux
Reflux
Reflux
Reflux
Reflux
Reflux
91
80
80
75
78
82
80
—
15
15
20
16
14
16
InCl3
Water
Water
Water
Water
Water
Water
ZnCl2
FeCl3
SnCl2
L-Proline
PTSA
Table 3
Synthesis of 6a–n under green condition.
Entry
1
Starting material used 2a–n
Product obtained 6a–n
Time (min)
60
Yield
91
mp (°C)
287–289
2
120
72
220–222
3
120
76
209–211
4
90
80
202–204
(Continues)
Journal of Heterocyclic Chemistry
DOI 10.1002/jhet

Month 2017
Diversity-oriented Multicomponent Synthesis of Bisquinolones under
Green Conditions
Table 3
(Continued)
Entry
5
Starting material used 2a–n
Product obtained 6a–n
Time (min)
90
Yield
84
mp (°C)
190–192
6
90
83
174–175
7
60
88
Above 300
8
60
85
296–298
9
60
85
293–294
10
120
75
237–238
11
120
71
240–242
(Continues)
Journal of Heterocyclic Chemistry
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M. Bandi and C. V. R. Reddy
Vol 000
Table 3
(Continued)
Entry
12
Starting material used 2a–n
Product obtained 6a–n
Time (min)
60
Yield
89
mp (°C)
290–292
13
90
82
242–243
14
90
84
265–266
was carried out under refluxing conditions 6a was found as a
major product. However, reaction in water under refluxing
conditions for 2–3 h gave, reasonably, high yield (91%) of
the product 6a (Table 1, entry 2). All these results were
summarized in Table 1.
Next, the reaction conditions were optimized for the
aforementioned reaction in order to know the best
catalyst. Thus, the aforementioned reaction was carried
out in water by using different types of Lewis acid
catalysts like SnCl2, InCl3, ZnCl2, FeCl3, L-Proline,
and PTSA. But in presence of catalyst, the reaction
was proceeded via formation of 7a along with 6a
(Scheme 3). However, reaction in water without
catalyst under refluxing conditions for 2–3 h gave,
reasonably, high yield (91%) of the product 6a
(Table 2, entry 1).
equivalent of 1 to yield the keto–enol intermediate III
followed by isomerisation of the latter intermediate
yielding the final product 6.
With the optimized conditions in hand, to delineate
this approach, the scope and generality of this protocol
were next accessed by employing various aromatic
aldehydes 2a–n to synthesize the corresponding divers
3,30-(phenylmethylene)bis(4-hydroxy-1-methylquinolin-2
(1H)-one). An assembly of 14 compounds was
synthesized by using this protocol. The reaction could
tolerate various substitutions on aromatic aldehydes.
Notably, aromatic aldehydes bearing electron-
withdrawing groups (Cl, F, NO2, etc.) at the aryl ring
afforded the desired products with excellent efficiency
(Table 3).
A plausible mechanism has been proposed for the
formation of 6. Initially, one equivalent of N-
methylquinolone (1) undergoes simple Knoevenagel
condensation with the activated aldehyde (2) to yield an
intermediate (I). If I undergoes nucleophilic addition with
aniline (3), it leads to formation of intermediate (IV).
And finally, IV was cyclized followed by aerial oxidation
to afford expected product 4. But original reaction
pathway is completely different from the expected
pathway. In this mechanism, dehydration of intermediate
(I) leads to II, which acts as a strong Michael acceptor.
The latter undergoes Michael addition with another
CONCLUSIONS
In summary, we have described an unexpected and
interesting reaction between N-methylquinolone, various
benzaldehydes, and aniline in which different
bisquinolone derivatives are formed. The products were
produced under classic reaction conditions in presence of
water as an available green solvent. The syntheses are
eco-friendly involving easy workup; moreover, they gave
high yields without the need of costly catalyst and
column chromatography.
Journal of Heterocyclic Chemistry
DOI 10.1002/jhet

Month 2017
Diversity-oriented Multicomponent Synthesis of Bisquinolones under
Green Conditions
EXPERIMENTAL
3,30-((4-Hydroxyphenyl)methylene)bis(4-hydroxy-1-
methylquinolin-2(1H)-one) (5c).
IR (KBr): 2985 (ꢀOH
group, broad), 2925 (ꢀOH group, broad), 1664, cmꢀ1
(ꢀCO– group, sharp);1H-NMR (DMSO-d6/TMS,
400 MHZ): δ 3.68 (s, 6H, ꢀ(CH3)2), 6.29 (s, 1H, ꢀCH),
7.20–8.44 (m, 12H, Ar–H), 12.23 (s, 1H, ꢀOH, D2O
exchangeable); 12.40 (s, 2H, ꢀOH, D2O exchangeable);
13C NMR (100 MHz; DMSO-d6): δC 18.71, 55.42,
115.62, 117.47, 123.11, 123.92, 126.24, 126.39, 128.82,
131.73, 137.61, 138.83, 160.75. m/z (M++1): 455. Anal.
Calcd for C27H22N2O5 (454.47): C, 71.31; H, 4.83; N,
General information. Melting points are uncorrected
and were determined in open capillary tubes in
sulphuric acid bath. TLC was run on silica gel – G and
visualization was done using iodine or UV light. IR
spectra were recorded using PerkinElmer 1000
instrument in KBr pellets. 1H-NMR spectra were
recorded in DMSO-d6 using TMS as internal standard
on
a 400-MHz spectrometer. Mass spectra were
recorded on Agilent LC-MS instrument under CI
conditions and given by Q + 1 value only. Starting
material 1 was prepared by using previously reported
procedure [24]. Compounds 2 and 3 were obtained
from commercial suppliers and used as such.
6.13; found: C, 71.22; H, 4.94; N, 6.16.
3,30-((2-Chlorophenyl)methylene)bis(4-hydroxy-1-
methylquinolin-2(1H)-one) (5d).
IR (KBr): 2985 (ꢀOH
group, broad), 1664 cmꢀ1 (ꢀCO– group, sharp);1H-NMR
(DMSO-d6/TMS, 400 MHZ): δ 3.71 (s, 6H, ꢀ(CH3)2),
6.31 (s, 1H, ꢀCH), 7.29–8.38 (m, 12H, Ar–H), 12.48 (s,
2H, ꢀOH, D2O exchangeable); 13C NMR (100 MHz;
DMSO-d6): δC 18.16, 55.32, 115.71, 117.16, 123.72,
123.89, 126.21, 126.62, 128.34, 131.91, 137.26, 137.51,
138.29, 138.53, 160.34. m/z (M+ + 1): 473. Anal. Calcd
Typical procedure for the preparation of 6 from 1, 2, and 3
by multi-component method. A mixture of 1(10 mmol), 2
(10 mmol), 3 (10 mmol), and water (5 mL) was refluxed
for 2–3 h. The latter was filtered to collect the insoluble
solid by filtration, and the insoluble solid was washed
with methanol (10 mL
× 3) and dried. It was
for C27H21ClN2O4 (472.92): C, 68.57; H, 4.48; N, 5.92;
recrystallized from methanol to obtain pure 6.
found: C, 68.53; H, 4.45; N, 5.98.
Typical procedure for the preparation of 6 from 1 and 2.
A mixture of 1 (10 mM), 2 (5 mM), and water (20 mL) was
refluxed at 100°C for 1 h. The reaction was monitored by
checking TLC for the disappearance of the starting
material, that is, 2. At the end of this period, a colorless
solid separated out from the reaction mixture, which was
collected by filtration. The crude product was then
washed with methanol (10 mL) and dried. It was
3,30-((3-Chlorophenyl)methylene)bis(4-hydroxy-1-
methylquinolin-2(1H)-one) (5e).
IR (KBr): 2975 (ꢀOH
group, broad), 1673 cmꢀ1 (ꢀCO– group, sharp);1H-
NMR (DMSO-d6/TMS, 400 MHZ): δ 3.83 (s, 6H,
ꢀ(CH3)2), 6.46 (s, 1H, ꢀCH), 7.41–8.72 (m, 12H,
Ar–H), 12.13 (s, 2H, ꢀOH, D2O exchangeable); 13C
NMR (100 MHz; DMSO-d6): δC 18.19, 55.28, 115.63,
117.26, 123.28, 123.72, 126.38, 126.75, 128.18,
131.82, 137.37, 137.81, 138.01, 138.28, 160.46. m/z
recrystallized from methanol to obtain pure 6.
3,30-(Phenylmethylene)bis(4-hydroxy-1-methylquinolin-2(1H)-
(M+
+ 1): 473. Anal. Calcd for C27H21ClN2O4
one) (5a).
IR (KBr): 2970 (ꢀOH group, broad),
(472.95): C, 68.54; H, 4.49; N, 5.96; found: C, 68.52;
1627 cmꢀ1 (ꢀCO– group, sharp);1H-NMR (DMSO-d6/
TMS, 400 MHZ): δ 3.72 (s, 6H, ꢀ(CH3)2), 6.28 (s,
1H, ꢀCH), 7.06–8.07 (m, 13H, Ar–H), 12.60 (s, 2H,
ꢀOH, D2O exchangeable); 13C NMR (100 MHz;
DMSO-d6): δC 18.88, 55.36, 115.71, 117.26, 123.12,
123.99, 126.02, 126.57, 128.43, 131.97, 137.99,
138.51, 160.87. m/z (M+ + 1): 439. Anal Calcd for
H, 4.48; N, 5.94.
3,30-((4-Chlorophenyl)methylene)bis(4-hydroxy-1-
methylquinolin-2(1H)-one) (5f).
IR (KBr): 2979 (ꢀOH
group, broad), 1683 cmꢀ1 (ꢀCO– group, sharp);1H-NMR
(DMSO-d6/TMS, 400 MHZ): δ 3.48 (s, 6H, ꢀ(CH3)2),
6.96 (s, 1H, ꢀCH), 7.23–8.61 (m, 12H, Ar–H), 12.36 (s,
2H, ꢀOH, D2O exchangeable); 13C NMR (100 MHz;
DMSO-d6): δC 18.62, 55.31, 115.81, 117.26, 123.62,
123.83, 126.36, 126.71, 128.76, 131.28, 137.51, 138.76,
160.69. m/z (M++1): 473. Anal. Calcd for C27H21ClN2O4
(472.92): C, 68.57; H, 4.48; N, 5.92; found: C, 68.53; H,
C27H22N2O4 (438.47): C, 73.96; H, 5.06; N, 6.39;
found: C, 73.84; H, 5.03; N, 6.28.
3,30-((2-Hydroxyphenyl)methylene)bis(4-hydroxy-1-
methylquinolin-2(1H)-one) (5b).
IR (KBr): 2972 (ꢀOH
group, broad), 2968 (ꢀOH group, broad), 1638, cmꢀ1
(ꢀCO– group, sharp);1H-NMR (DMSO-d6/TMS,
400 MHZ): δ 3.79 (s, 6H, ꢀ(CH3)2), 6.35 (s, 1H, ꢀCH),
7.12–8.32 (m, 12H, Ar–H), 12.16 (s, 1H, ꢀOH, D2O
exchangeable); 12.38 (s, 2H, ꢀOH, D2O exchangeable);
13C NMR (100 MHz; DMSO-d6): δC 18.71, 55.24,
115.62, 117.51, 123.24, 123.83, 126.11, 126.72, 128.24,
131.95, 137.14, 138.63, 160.69. m/z (M+ + 1): 455. Anal.
Calcd for C27H22N2O5 (454.47): C, 71.35; H, 4.88; N,
6.16; found: C, 71.28; H, 4.91; N, 6.18.
4.45; N, 5.98.
3,30-((2-Nitrophenyl)methylene)bis(4-hydroxy-1-methylquinolin-
2(1H)-one) (5g). IR (KBr): 2981 (ꢀOH group, broad),
1698 cmꢀ1 (ꢀCO– group, sharp);1H-NMR (DMSO-d6/
TMS, 400 MHZ): δ 3.61 (s, 6H, ꢀ(CH3)2), 6.72 (s, 1H,
ꢀCH), 7.81–8.43 (m, 12H, Ar–H), 12.51 (s, 2H, ꢀOH,
D2O exchangeable); 13C NMR (100 MHz; DMSO-d6): δC
18.27, 55.46, 115.71, 117.34, 123.51, 123.82, 126.41,
126.85, 128.23, 131.72, 137.29, 137.76, 138.13, 138.42,
160.72. m/z (M++1): 484. Anal. Calcd for C27H21N3O6
Journal of Heterocyclic Chemistry
DOI 10.1002/jhet

M. Bandi and C. V. R. Reddy
Vol 000
(483.47): C, 67.07; H, 4.38; N, 8.69; found: C, 67.08; H,
7.25–8.41 (m, 10H, Ar–H), 9.31(s, 1H, ꢀOH, D2O
exchangeable); 12.72 (s, 2H, ꢀOH, D2O exchangeable);
13C NMR (100 MHz; DMSO-d6): δC 18.27, 55.41,
115.61, 117.37, 123.42, 123.83, 126.35, 126.81, 128.38,
131.29, 137.58, 137.91, 138.36, 138.67, 160.74. m/z
(M++1): 545. Anal. Calcd for C27H20N4O7 (544.47):
C, 59.56; H, 3.70; N, 10.29; found: C, 59.54; H, 3.73;
4.34; N, 8.65.
3,30-((3-Nitrophenyl)methylene)bis(4-hydroxy-1-methylquinolin-
2(1H)-one) (5h). IR (KBr): 2986 (ꢀOH group, broad),
1679 cmꢀ1 (ꢀCO– group, sharp);1H-NMR (DMSO-d6/
TMS, 400MHZ): δ 3.82 (s, 6H, ꢀ(CH3)2), 6.46 (s,
1H, ꢀCH), 7.82–8.49 (m, 12H, Aromatic hydrogens),
12.62 (s, 2H, ꢀOH, D2O exchangeable); 13C NMR
(100 MHz; DMSO-d6): δC 18.31, 55.36, 115.52,
117.29, 123.38, 123.91, 126.71, 126.79, 128.38,
131.57, 137.35, 137.62, 138.29, 138.58, 160.59. m/z
(M++1): 484. Anal. Calcd for C27H21N3O6 (483.43):
C, 67.02; H, 4.31; N, 8.69; found: C, 67.03; H, 4.32;
N, 8.61.
N, 10.25.
3,30-(Furan-2-ylmethylene)bis(4-hydroxy-1-methylquinolin-
2(1H)-one) (5m). IR (KBr): 2973 (ꢀOH group, broad),
1
1689 cmꢀ1 (ꢀCO– group, sharp); H-NMR (DMSO-d6/
TMS, 400 MHZ): δ 3.52 (s, 6H, ꢀ(CH3)2), 6.83 (s,
1H, ꢀCH), 7.63–8.89 (m, 11H, Ar–H), 12.13 (s, 2H,
ꢀOH, D2O exchangeable); 13C-NMR (100 MHz;
DMSO-d6): δC 20.89, 56.45, 119.64, 121.17, 124.33,
125.24, 128.62, 129.51, 132.84, 137.93, 139.73,
160.72. m/z (M++1): 429. Anal. Calcd for C25H20N2O5
(428.44): C, 70.08; H, 4.71; N, 6.54; found: C, 70.04;
3,30-((4-Nitrophenyl)methylene)bis(4-hydroxy-1-methylquinolin-
2(1H)-one) (5i).
IR (KBr): 2991 (ꢀOH group, broad),
1685 cmꢀ1 (ꢀCO– group, sharp);1H-NMR (DMSO-d6/
TMS, 400 MHZ): δ 3.87 (s, 6H, ꢀ(CH3)2), 6.63 (s, 1H,
ꢀCH), 7.92–8.41 (m, 12H, Ar–H), 12.83 (s, 2H, ꢀOH,
D2O exchangeable); 13C NMR δC (100 MHz;
DMSO-d6): 18.27, 55.31, 115.46, 117.69, 123.26,
123.71, 126.53, 126.77, 128.81, 131.68, 137.19, 138.81,
160.93. m/z (M++1): 484. Anal. Calcd for C27H21N3O6
(483.49): C, 67.02; H, 4.36; N, 8.64; found: C, 67.01; H,
H, 4.76; N, 6.58.
3,30-(Thiophen-2-ylmethylene)bis(4-hydroxy-1-methylquinolin-
2(1H)-one) (5n). IR (KBr): 2914 (ꢀOH group, broad),
1685 cmꢀ1 (ꢀCO– group, sharp);1H-NMR (DMSO-d6/
TMS, 400 MHZ): δ 3.73 (s, 6H, ꢀ(CH3)2), 6.81 (s,
1H, ꢀCH), 7.55–8.61 (m, 11H, Ar–H), 12.92 (s, 2H,
ꢀOH, D2O exchangeable); 13C-NMR (100 MHz;
DMSO-d6,): δC 19.62, 57.47, 120.82, 122.77, 123.18,
127.55, 128.57, 130.76, 133.88, 138.73, 140.26,
160.91. m/z (M++1): 445. Anal. Calcd for
C25H20N2O4S (444.50): C, 67.55; H, 4.54; N, 6.30;
found: C, 67.52; H, 4.58; N, 6.34.
4.32; N, 8.63.
3,30-((4-Methoxyphenyl)methylene)bis(4-hydroxy-1-
methylquinolin-2(1H)-one) (5j).
IR (KBr): 2976 (ꢀOH
group, broad), 1672 cmꢀ1 (ꢀCO– group, sharp);1H-
NMR (DMSO-d6/TMS, 400 MHZ): δ 3.51 (s, 6H,
ꢀ(CH3)2), 3.83 (s, 3H, ꢀOCH3), 6.84 (s, 1H, ꢀCH),
7.58–8.72 (m, 12H, Ar–H), 12.91 (s, 2H, ꢀOH, D2O
exchangeable); 13C NMR (100 MHz; DMSO-d6): δC
18.11, 42.26, 55.42, 115.61, 117.72, 123.51, 123.85,
126.53, 126.79, 128.67, 131.73, 137.27, 138.66,
160.58. m/z (M++1): 469. Anal. Calcd for C28H24N2O5
(468.50): C, 71.78; H, 5.16; N, 5.98; found: C, 71.76;
Acknowledgments. Authors are thankful to the authorities of
Jawaharlal Nehru Technological University Hyderabad for
providing laboratory facilities.
H, 5.19; N, 5.95.
REFERENCES AND NOTES
3,30-((3-Ethoxy-4-methoxyphenyl)methylene)bis(4-hydroxy-
1-methylquinolin-2(1H)-one) (5k). IR (KBr): 2982 (ꢀOH
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Journal of Heterocyclic Chemistry
DOI 10.1002/jhet

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Diversity-oriented Multicomponent Synthesis of Bisquinolones under
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DOI 10.1002/jhet