Facile heteropolyacid-promoted synthesis of indeno[1,2-b]quinoline-9,11(6H, 10H)-dione derivatives

Article abstract of DOI:10.1080/00397910903219591

An efficient synthesis of indeno[1,2-b]quinoline-9,11(6H,10H)-dione derivatives was reported via four-component coupling reaction of aldehydes, dimedone, 1,3-indandione, and amines in refluxing ethanol or three-component condensation of aldehydes, 1,3-ind

Full text of DOI:10.1080/00397910903219591

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Facile Heteropolyacid-Promoted
Synthesis of Indeno[1,2-
b]quinoline-9,11(6H,10H)-dione
Derivatives
Majid M. Heravi a , Hamideh Alinejhad a , Khadijeh Bakhtiari a
, Zohreh Daroogheha a , Fatemeh F. Bamoharram b , Fatemeh
Derikvand a & Behnoush Alimadadi a
a Department of Chemistry, School of Sciences, Azzahra University,
Vanak, Tehran, Iran
b Department of Chemistry, Islamic Azad University, Mashhad
Branch, Mashhad, Iran
Published online: 07 Jul 2010.
To cite this article: Majid M. Heravi , Hamideh Alinejhad , Khadijeh Bakhtiari , Zohreh Daroogheha ,
Fatemeh F. Bamoharram , Fatemeh Derikvand & Behnoush Alimadadi (2010): Facile Heteropolyacid-
Promoted Synthesis of Indeno[1,2-b]quinoline-9,11(6H,10H)-dione Derivatives, Synthetic
Communications: An International Journal for Rapid Communication of Synthetic Organic Chemistry,
40:15, 2191-2200
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Synthetic Communications1, 40: 2191–2200, 2010
Copyright # Taylor & Francis Group, LLC
ISSN: 0039-7911 print=1532-2432 online
DOI: 10.1080/00397910903219591
FACILE HETEROPOLYACID-PROMOTED SYNTHESIS
OF INDENO[1,2-b]QUINOLINE-9,11(6H,10H)-DIONE
DERIVATIVES
Majid M. Heravi,1 Hamideh Alinejhad,1 Khadijeh Bakhtiari,1
Zohreh Daroogheha,1 Fatemeh F. Bamoharram,2
Fatemeh Derikvand,1 and Behnoush Alimadadi1
1Department of Chemistry, School of Sciences, Azzahra University, Vanak,
Tehran, Iran
2Department of Chemistry, Islamic Azad University, Mashhad Branch,
Mashhad, Iran
An efficient synthesis of indeno[1,2-b]quinoline-9,11(6H,10H)-dione derivatives was
reported via four-component coupling reaction of aldehydes, dimedone, 1,3-indandione,
and amines in refluxing ethanol or three-component condensation of aldehydes, 1,3-
indandione, and 5,5-dimethyl-3-arylamino-cyclohex-2-enone derivatives at 120 ꢀC under
solvent-free conditions in the presence of a catalytic amount of Preyssler-type heteropoly-
acid, H14[NaP5W30O110], as a green and reusable catalyst.
Keywords: Indeno[1,2-b]quinoline-9,11(6H,10H)-dione derivatives; multicomponent reactions; Preyssler-
type heteropolyacid; solvent-free synthesis
INTRODUCTION
Quinoline derivatives have attracted increasing interest because of their diverse
pharmacological properties, such as antiplasmodial,[1] intrinsic,[2] cytotoxic,[3] func-
tional,[4] antibacterial,[5] antiproliferative,[6] antimalarial,[7] and anticancer activi-
ties.[8] In addition to medicinal applications, quinoline derivatives undergo
hierarchical self-assembly into a variety of nanostructures and mesostructures
with enhanced electronic and photonic functions.[9] Considering their significant
applications in the fields of medicinal, bioorganic, industrial, and synthetic organic
chemistry, there has been tremendous interest in developing efficient methods for
the synthesis of known quinolines or new procedures for the synthesis of novel
quinoline derivatives.
In spite of the importance of indenoquinoline derivatives, few methods for the
production of these compounds have been reported. Recently, the synthesis of
indeno[1,2-b]quinoline derivatives was reported by Tu and coworkers.[10] Moreover,
Received May 28, 2009.
Address correspondence to Khadijeh Bakhtiari, Department of Chemistry, School of Sciences,
Azzahra University, Vanak, Tehran, Iran. E-mail: khb1352@yahoo.com
2191

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M. M. HERAVI ET AL.
Scheme 1. Four-component synthesis of indeno[1,2-b]quinoline-9,11(6H,10H)-dione derivatives catalyzed
by heteropolyacid under solvent-free conditions.
Scheme 2. Synthesis of enaminone derivatives catalyzed by heteropolyacid under solvent-free conditions.
Scheme 3. Three-component synthesis of indeno[1,2-b]quinoline-9,11(6H,10H)-dione derivatives cata-
lyzed by heteropolyacid under solvent-free conditions.
these compounds have been prepared in ionic liquid at 90 ꢀC.[11] These methods,
however, involve long reaction times, harsh reaction conditions, and the use of
microwave irradiation.
In recent years, the use of Preyssler-type heteropolyacid as a heterogeneous
catalyst has received great interest in organic synthesis.[12]
In continuation of our work to develop new synthetic methodologies under
ecofriendly conditions,[13–15] we report here an efficient synthesis of indeno[1,2-
b]quinoline-9,11(6H,10H)-dione derivatives via four-component coupling reaction
of aldehydes, dimedone, 1,3-indandione, and amines in refluxing ethanol or by
three-component reactions of aldehydes, 1,3-indandione, and 5,5-dimethyl-3-aryl-
amino-cyclohex-2-enone derivatives at 120 ꢀC under solvent-free conditions in the
presence of a catalytic amount of Preyssler-type heteropolyacid, H14[NaP5W30O110],
a green and reusable catalyst (Schemes 1–3).
RESULTS AND DISCUSSION
First, a mixture of 4-nitro benzaldehyde, dimedone, 1,3-indandione, and
4-methylaniline in refluxing ethanol was chosen as a model reaction (Scheme 1) to
detect whether the use of heteropolyacid as catalyst was efficient and to investigate
the optimized conditions. The results are summarized in Table 1.

SYNTHESIS OF INDENO[1,2-b]QUINOLINEDIONES
Table 1. Detection of the reaction conditionsa
2193
Entry
Amount of catalyst (g)
Time (h)
Yield (%)b
1
2
3
4
—
24
24
No reaction
0.01
0.03
0.1
20
70
70
2.5
2.5
aAll reactions were run in 4-nitro benzaldehyde, dimedone, 1,3-indandione,
and 4-methylaniline 1:1:1:1 (mmol) in refluxing ethanol.
bYields are related to isolated pure products.
Increasing the amount of catalyst from 0.01 to 0.03 g (0.42 mol%) could
improve the reaction significantly. Inspired by the results, we changed the amount
of the catalyst from 0.03 to 0.1 g, finding that 0.03 g of heteropolyacid (0.42 mol%)
was good enough (Table 1).
The optimized conditions were used to construct a variety of indeno[1,2-
b]quinoline-9,11(6H,10H)-dione derivatives. It was found that this method is
effective with a variety of substituted aromatic aldehydes independent of the nature
of the substituents in the aromatic ring (Table 2).
In another set of experiments, we made enaminone derivatives independently
and used them for a three-component, one-pot synthesis of indeno[1,2-b]-
quinoline-9,11(6H,10H)-dione derivatives from the condensation of enaminones,
1,3-indandione, and aldehyde derivatives in the presence of a catalytic amount
of H14NaP5W30O110 (0.42 mol%) at 120 ꢀC, under solvent-free conditions
(Schemes 2 and 3). As shown in Table 3, in this way, the desired products
were obtained in shorter times and better yields than with the four-component
procedure.
We also examined the reusability of the catalyst system. Because heteropo-
lyacid was weakly soluble in diethyl ether, it can be separated by washing
with Et2O and drying at 80 ꢀC under reduced pressure and then reused for
the reactions. We observed that the amount of the catalyst system was reduced
to approximately 90% of initial amount after three cycles, which resulted from
partial solubility of heteropolyacid in diethyl ether and ethanol. The isolated
yields obtained for three cycles are also in the same range as those observed
for the one-cycle reaction presented in Tables 4 and 5. The performance of
the recovered catalyst during the synthesis of indeno[1,2-b]quinoline-9,11(6H,
10H)-diones was found to be satisfactory with no considerable variation
in yield.
The plausible mechanism for this synthesis is shown in Scheme 4.
In summary, herein we report two high-yielding, simple, convenient,
straightforward, and practical one-pot procedures for the synthesis of 5,10-
diaryl-7,8-dihydro-7,7-dimethyl-5H-indeno[1,2-b]-quinolin-9,11(6H,10H)-dione deri-
vatives. The conditions are mild, and a wide range of functional groups can be
tolerated. Using heteropolyacid as catalyst offers advantages including simplicity
of operation, easy workup, recycling of the catalyst, and excellent yields of
products.

2194
M. M. HERAVI ET AL.
Table 2. Four-component synthesis of 5,10-diaryl-7,8-dihydro-7,7-dimethyl-5H-indeno[1,2-b]-quinolin-
9,11(6H,10H)-dione in refluxing ethanol
Mp (ꢀC)
Entry
ArNH2
Product
Time (h)
Yield (%)a
Obtained
283–285
Reported[10,11]
1
3:30
73
283–285
2
2:00
74
290–291
290–291
3
3:00
70
223–225
225–227
4
3:00
70
255–257
255–256
5
6
1:10
0:55
73
71
293–294
257–258
291–293
257–258
aYields are related to isolated pure products.

SYNTHESIS OF INDENO[1,2-b]QUINOLINEDIONES
2195
Table 3. Three-component synthesis of 5,10-diaryl-7,8-dihydro-7,7-dimethyl-5H-indeno[1,2-b]-quinolin-
9,11(6H,10H)-dione from the reaction of arylaldehydes, enaminones, and 1,3-indandione at 120 ꢀC under
solvent-free conditions
Entry
ArNH2
Product
Time (h)
Yield (%)a
1
2:00
88
2
3
4
1:20
1:40
2:00
90
88
87
5
1:10
73
6
0:55
71
aYields are related to isolated pure products.

2196
M. M. HERAVI ET AL.
Table 4. Efficiency of the recovered catalyst in four-component
synthesis of 7,8-dihydro-7,7-dimethyl-10-(4-nitrophenyl)-5-(p-tolyl)-
5H-indeno[1,2-b]-quinolin-9,11(6H,10H)-dione
Cycle
Yield (%)a
1
2
3
74
70
70
aYields are related to isolated pure products.
Table 5. Efficiency of the recovered catalyst in three-component
synthesis of 7,8-dihydro-7,7-dimethyl-10-(4-nitrophenyl)-5-(p-tolyl)-
5H-indeno[1,2-b]-quinolin-9,11(6H,10H)-dione
Cycle
Yield (%)a
1
2
3
90
87
80
aYields are related to isolated pure products.
Scheme 4. Plausible mechanism for the synthesis of indeno[1,2-b]quinoline-9,11(6H,10H)-dione derivatives.
EXPERIMENTAL
Melting points were measured by using the capillary tube method with a
1
Bamstead Electrothermal 9200 apparatus and are uncorrected. H NMR and 13C
NMR spectra were recorded on a Bruker AQS 300 or 500 Avance spectrometers

SYNTHESIS OF INDENO[1,2-b]QUINOLINEDIONES
2197
(75 or 125 MHz for 13CNMR), using tetramethylsilane (TMS) as an internal
standard (CDCl3 solution). Infrared (IR) spectra were recorded from KBr disk on
the Fourier transform (FT)–IR Bruker Tensor 27. The reactions were monitored
by thin-layer chromatography (TLC). All solvents and reagents were purchased from
Aldrich and Merck with high-grade quality and used without any purification. All
products were characterized by their spectra and physical data.
Four-Component Synthesis of Indeno[1,2-b]-quinolin Derivatives
in Refluxing Ethanol
General procedure. A solution of an aromatic aldehyde (1 mmol), dimedone
(1 mmol), 1.3-indandione (1 mmol), aniline derivative (1 mmol), and H14NaP5W30O110
(0.42 mol%) was stirred in ethanol (5 ml) under refluxing conditions for an appro-
priate time. After completion of the reaction, which was monitored by TLC, the
catalyst was filtered off, and the solvent was evaporated under reduced pressure.
The resulting crude product was purified by column chromatography.
Recycling of the catalyst. After completion of the reaction, the catalyst was
recycled by simple filtration, washed with diethyl ether, dried, and reused for the next
reaction with only a modest loss in activity. The catalyst was recovered and reused
three times for the synthesis of 7,8-dihydro-7,7-dimethyl-10-(4-nitrophenyl)-5-(p-
tolyl)-5H-indeno[1,2-b]-quinolin-9,11-(6H,10H)-dione, and the obtained results are
summarized in Table 4.
Three-Component Synthesis of Indeno[1,2-b]-quinolin Derivatives
at 120 ꢀC Under Solvent-Free Conditions
Synthesis of 3-Arylamino-5,5-dimethylcyclohex-2-enone (enaminone
derivative). A solution of an aniline derivative (20 mmol), dimedone (20 mmol),
and H14NaP5W30O110 (1 mol%) was stirred in ethanol (5 ml) under refluxing con-
ditions for 2 h. After completion of the reaction, the catalyst was filtered off, and
the mixture was cooled to room temperature. The resulting solid product was
then removed by filtration and recrystallized from absolute ethanol to give the pure
product.
The pure enaminone derivative was then used for the synthesis of indeno[1,2-
b]-quinolin derivatives.
Synthesis of indeno[1,2-b]-quinolin derivatives. A solution of an aro-
matic aldehyde (1 mmol), enaminone derivative (1 mmol), 1,3-indandione (1 mmol),
and H14NaP5W30O110 (0.42 mol%) was stirred at 120 ꢀC for an appropriate time.
After completion of the reaction, which was monitored by TLC, the mixture was
cooled to room temperature and washed with water to separate the catalyst. The
obtained crude product was then purified by column chromatography.
Recycling of the catalyst. H14NaP5W30O110 is soluble in water. Therefore,
after completion of the reaction, the reaction mixture was washed with water.
The catalyst was recovered after evaporation of water under reduced pressure.
The recycled catalyst was washed with diethyl ether. The catalyst has been recovered

2198
M. M. HERAVI ET AL.
and reused for three times in the synthesis of 7,8-dihydro-7,7-dimethyl-10-
(4-nitrophenyl)-5-(p-tolyl)-5H-indeno[1,2-b]quinolin-9,11(6H,10H)-dione, and the
obtained results are summarized in Table 5.
Product Characterization Data
7,8-Dihydro-7,7-dimethyl-5,10-di(p-tolyl)-5H-indeno[1,2-b]quinoline-9,11-
(6H,10H)-dione. Mp 283–285 ꢀC; IR (KBr): tmax ¼ 2954, 2862, 1686, 1633, 158,
1561, 1510, 1462, 1392, 1363, 1254, 1225, 1171, 1140, 1099, 1046, 1019, 978, 940,
1
888 cmꢁ1. H NMR (CDCl3, 500 MHz): dH ¼ 0.96 (s, 3H, CH3), 1.05 (s, 3H, CH3),
2.1 (d, J ¼ 17.5 Hz, 1H, CH-6), 2.2 (d, J ¼ 11.2 Hz, 1H, CH-60), 2.23–2.31 (m, 5H,
CH2-8, CH3), 2.6 (s, 3H, CH3), 5.1(s, 1H, CH-10), 5.28 (d, J ¼ 7.5 Hz, 1H, ArH),
6.89 (d, 1H, J ¼ 1 Hz, ArH), 7.09–7.12 (m, 3H, ArH), 7.32–7.38 (m, 5H, ArH), 7.4
(d, J ¼ 8.16 Hz, 2H, ArH) ppm.
7,8-Dihydro-7,7-dimethyl-10-(4-nitrophenyl)-5-p-tolyl-5H-indeno[1,2-b]
quinoline-9,11-(6H,10H)-dione. Mp ¼ 290–291 ꢀC; IR (KBr): tmax ¼ 3073, 2956,
1676, 1634, 1591, 1560, 1513, 1449, 1392, 1366, 1344, 1255, 1224, 1194, 1168,
1
1146, 1096, 1059, 4,979, 889, 832 cmꢁ1. H NMR (CDCl3, 300 MHz): dH ¼ 0.92 (s,
3H, CH3), 1.03 (s, 3H, CH3), 2–2.32 (m, 4H, 2CH2-6 & 8), 2.58 (s, 3H, CH3), 5.2
(s, 1H, CH-10), 5.3 (d, J ¼ 7.5 Hz, 1H, ArH), 6.88–6.91 (m, 1H, ArH), 7.1 (t, 1H,
J ¼ 7.2, ArH), 7.3–7.35 (m, 3H, ArH), 7.43–7.45 (m, 2H, ArH), 7.6 (d, J ¼ 8.7 Hz,
2H, ArH), 8.1 (d, J ¼ 8.7 Hz, 2H, ArH) ppm. 13C NMR (CDCl3, 75 MHz):
dC ¼ 21.5, 26.9, 29.6, 32.3, 34.2, 41, 50, 111.6, 114.8, 121, 121.5, 123.7, 128.9,
129.2, 129.6, 130.9, 131.6, 133.3, 135.7, 137, 140.8, 146.4, 151.5, 152.6, 154.8,
191.8, 195.92 ppm.
10-(4-Fluorophenyl)-7,8-dihydro-7,7-dimethyl-5-(p-tolyl)-5H-indeno[1,2-
b]quinoline-9,11-(6H,10H)-dione. Mp 223–225 ꢀC; IR (KBr): tmax ¼ 2954, 2926,
1689, 1637, 1592, 1560, 1459, 1365, 1254, 1221, 1168, 1145, 888, 764 cmꢁ1 1H
.
NMR (CDCl3, 500 MHz): dH ¼ 0.94 (s, 3H, CH3), 1.05 (s, 3H, CH3), 2.1 (dd,
J ¼ 17.5 & 1.1 Hz, 1H, CH-6), 2.23–2.31 (m, 3H, CH-60 & CH2-8), 2.6 (s, 3H,
CH3), 5.1 (s, 1H, CH-10), 5.1 (s, 1H, CH), 5.3 (d, J ¼ 7.5 Hz, 1H, ArH), 6.97–7.01
(m, 2H, ArH), 7.12–7.15 (m, 1H, ArH), 7.35 (m, 3H, ArH), 7.43–7.46 (m, 4H,
ArH) ppm.
10-(4-Bromophenyl)-7,8-dihydro7,7-dimethyl-5-(p-tolyl)-5H-indeno[1,2-
b]quinoline-9,11-(6H,10H)-dione. Mp ¼ 255–257 ꢀC; IR (KBr): tmax ¼ 3043, 2959,
2877, 1688, 1638, 1584, 1559, 1510, 1482, 1455, 1364, 1254, 1223, 1188, 1141, 1102,
1
1064, 888, 762 cmꢁ1. H NMR (CDCl3, 500 MHz): dH ¼ 0.94 (s, 3H, CH3), 1.05 (s,
3H, CH3), 2.2–2.31 (m, 4H, CH2-6 & 8), 2.6 (s, 3H, CH3), 5.1 (s, 1H, CH-10), 5.3
(d, J ¼ 7.5 Hz, 1H, ArH), 6.9–6.93 (m, 1H, ArH), 7.12 (t, 1H, J ¼ 7.2 Hz, ArH),
7.3–7.38 (m, 5H, ArH), 7.42–7.45 (m, 4H, ArH) ppm.
10-(2,4-Dichlorophenyl)-7,8-dihydro7,7-dimethyl-5-p-tolyl-5H-indeno[1,
2-b]quinoline-9,11(6H,10H)-dione. Mp ¼ 293–294 ꢀC; IR (KBr): tmax ¼ 3065,
2955, 2864, 1687, 1635, 1561, 1511, 1463, 1393, 1364, 1309, 1171, 1101, 978,
1
889 cmꢁ1. H NMR (CDCl3, 500 MHz): dH ¼ 0.98 (s, 3H, CH3), 1.04 (s, 3H, CH3),
2.1 (d, J ¼ 17.5 Hz, 1H, CH-6), 2.2–2.28 (m, 3H, CH-60, CH2-8), 2.6 (s, 3H, CH3),

SYNTHESIS OF INDENO[1,2-b]QUINOLINEDIONES
2199
5.28 (d, J ¼ 7.5 Hz, 1H, ArH), 5.4 (s, 1H, CH-10), 6.85–6.95 (m, 1H, ArH), 7.11–7.14
(t, 1H, J ¼ 7.3 Hz, ArH), 7.2 (dd, 1H, J ¼ 8.24 & 2.1 Hz, ArH), 7.3–7.36 (m, 4H,
ArH), 7.4 (d, J ¼ 8 Hz, 2H, ArH), 7.53 (d, J ¼ 8.3 Hz, 1H, ArH) ppm.
7,8-Dihydro-7,7-dimethyl-5,10-diphenyl-5H-indeno[1,2-b]quinoline-9,11-
(6H,10H)-dione. Mp 257–258 ꢀC; IR (KBr): tmax ¼ 3061, 3025, 2928, 2955, 2928,
1688, 1634, 1587, 1557, 1490, 1453, 1391, 1366, 1253, 1222, 1193, 1169, 1139,
.
1098, 1060, 1022, 975, 937, 885, 838, 761 cmꢁ1 1H NMR (CDCl3, 500 MHz):
dH ¼ 0.95 (s, 3H, CH3), 1.05 (s, 3H, CH3), 2 (dd, J ¼ 17.5 & 1.1 Hz, 1H, CH-6),
2.2 (dd, J ¼ 16.3 & 1.2 Hz, 1H, CH-60), 2.3 (d, J ¼ 16.6 Hz, 2H, CH2-8), 5.17–5.21
(m, 1H, ArH), 5.3 (s, 1H, CH-10),6.8 (d, 1H, J ¼ 1.1, ArH), 7.11 (s, 1H, ArH),
7.17 (s, 1H, ArH), 7.3–7.34 (m, 3H, ArH), 7.49–7.51 (m, 4H, ArH), 7.64–7.71 (m,
3H, ArH) ppm.
ACKNOWLEDGMENT
The authors are thankful to Azzahra Research Council for the partial financial
support.
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