Facile three-component one-pot synthesis of indeno-[1,2-b]quinolin-9,11(6H, 10H)-dione derivatives

Article abstract of DOI:10.1002/jhet.5570440538

(Chemical Equation Presented) One-pot three-component cyclocondensation of aldehydes, 1,3-indanedione and enaminones proceeds in the presence of acetic acid to afford Indeno[1,2-b]quinolin-9,11(6H,10H)-dione derivatives, The method has the advantage of ex

Full text of DOI:10.1002/jhet.5570440538

Sep-Oct 2007
1201
Facile Three-component One-pot Synthesis of Indeno-
[1,2-b]quinolin-9,11(6H,10H)-dione Derivatives
Yan Chena, Shujiang Tub,*, Bo Jiangb, Feng Shib
aDepartment of Chemistry, Xuzhou Education College, Xuzhou, Jiangsu 22100ꢀ, PR China
chenyan681110@126.com
bDepartment of Chemistry, Xuzhou Normal University, Key Laboratory of Biotechnology on Medical Plant,
Xuzhou, Jiangsu 221ꢁꢁ9, PR China, laotu2001@263.net
Received December 7, 2006
O
O
R
+
+
ArCHO
HN
Ar
R
O
3
1
2
O
O
R
acetic acid
120-140 oC, refluxing
N
R
4
One-pot three-component cyclocondensation of aldehydes, 1,3-indanedione and enaminones proceeds in
the presence of acetic acid to afford Indeno[1,2-b]quinolin-9,11(6H,10H)-dione derivatives, The method
has the advantage of excellent yields(85-94%) and simple workup procedure.
J. Heterocyclic Chem., 44, 1201 (2007).
series of indeno[1,2-b]quinolin-9,11(6H,10H)-dione deriv-
atives with aldehydes, 1,3-indanedione and enaminones in
actetic acid (Scheme 1). The initial results are
summarized in Table 1.
INTRODUCTION
Indenoquinoline derivatives have shown a diverse range
of biological properties such as 5-HT-receptor binding [1]
and anti-inflammatory activities [2]. They have also acted
as antitumor agents [3,4], steroid reductase inhibitors [5],
acetylcholinesterase inhibitors [6], antimalarials [7], and
new potential topo I/II inhibitors [8]. Because of these
biological activities they exhibit, these compounds have
distinguished themselves as heterocycles of profound
chemical and biological significance. Thus the synthesis
of these molecules has attracted considerable attention
[9,11]. Stankevich [12,13] et al. have reported the
synthesis of indeno[1,2-b]quinolin-9,11(6H,10H)-dione
derivatives via two-component reaction. However, the
introduction of a cyclopropyl group on the nitrogen atom
of indeno[1,2-b]quinoline skeleton is seldom investigated.
In this paper, we would like to report a highly efficient
method for the one-pot three-component synthesis of a
RESULTS AND DISCUSSION
The procedure is easy to operate and the workup
procedure is just simple filtrations. At the beginning,
we made a search for the aromatic aldehydes substrate
scope with 1,3-indanedione and enaminones 3a as
model substrates (Table 1, entries1-11), and the results
indicated that aromatic aldehydes bearing functional
groups such as nitro, bromo, chloro or methoxy, methy
were able to affect the synthesis of compounds 4. We
have also observed delicate electronic effects: that is,
aromatic aldehydes with electron-withdrawing groups
(Table 1, entries 1-6) reacted rapidly, while
substitution of electron-rich groups (Table 1, entries 8-
11) on the benzene ring decreased the reactivity,
Scheme 1
R
N
O
ArCHO
O
O
O
O
1
acetic acid
R1
R2
R1
R1
+
120-140 oC, refluxing
HN
4
2
3

1202
Y. Chen, S. Tu, B. Jiang, F. Shi
Vol 44
Table 1
Synthesis of Compounds 4
entry
Compd
Ar
3
R
Time
hours
Temp.
(oC)
Yield
%
Mp
(oC)
1
2
3
4
5
6
4a
4b
4c
4d
4e
4f
4-NO2C6H4
3-NO2C6H4
4-OH-3-NO2C6H3
4-FC6H4
3a
3a
3a
3a
3a
3a
CH3
CH3
CH3
CH3
CH3
CH3
2.0
2.0
2.0
2.0
2.0
2.0
120
120
120
120
120
120
94
94
92
93
92
91
268-270
258-260
245-247
264-266
295-297
297-298
4-ClC6H4
4-BrC6H4
7
4g
4h
4i
C6H5
3a
3a
3a
3a
3a
3b
3b
3b
3b
3b
3b
CH3
CH3
CH3
CH3
CH3
H
2.5
3.0
3.5
2.5
3.5
2.0
2.0
2.5
2.0
3.0
2.5
130
140
140
140
140
120
120
120
120
140
140
90
88
82
86
85
92
91
90
92
85
87
275-276
286-288
248-250
220-222
256-258
256-258
275-276
262-263
269-270
264-266
268-270
8
4-CH3C6H4
9
3,4(OCH2O)C6H3
4-CH3OC6H4
3,4-(CH3O)2C6H3
3-NO2C6H4
10
11
12
13
14
15
16
17
4j
4k
4l
4m
4n
4o
4p
4q
4-NO2C6H4
H
4-OH-3-NO2C6H3
4-FC6H4
H
H
4-CH3OC6H4
4-CH3C6H4
H
H
requiring longer reaction times. In order to further
expand the scope of the present method, the replace-
ment of 3-(cyclopropylamino)-5,5-dimethylcyclohex-
2-enone 3a with 3-(cyclopropylamino)cyclohex-2-
enone 3b was examined. To our delight, under the
same conditions, the reactions proceeded steadily to
afford a series of new poly-substituted indeno[1,2-b]-
quinolines in good yields (Table 1, entries 12-17).
The reaction may occur via condensation, addition,
cyclization and elimination. The condensation between
aldehydes 1 and 1,3-indanedione 2 gave 2-arylidene-
indene-1,3-dione 5, which further undergoes in situ
Michael addition reaction with enaminones 3 to yield
products 4 (Scheme 2).
product 4f in 92% yield, which is similar to that of the
above three-component method.
In order to support the proposed mechanism, the
compound 5 was prepared independently from p-bromo-
benzaldehyde 1f,ꢀ 1,3-indanedione 2 and then employed
in a two component reaction with enaminone 3 to afford
Figure 1. Molecular structure of 4d
Scheme
2
O
O
O
O
Ar
HC
ArCHO
+
1
5
2
Ar
N
O
O
O
Ar
O
O
-H2O
R1
R2
R1
R2
R1
R2
HN
HN
O
4
3

Sep-Oct 2007
Facile Three-component One-pot Synthesis of
1203
Indeno[1,2-b]quinolin-9,11(6H,10H)-dione Derivatives
17.2 Hz), 2.75 (d, 1H, CH2, J = 17.2 Hz), 2.26 (d, 1H, CH2, J =
16.0 Hz), 2.21 (d, 1H, CH2, J = 16.0 Hz), 1.31-1.34 (m, 2H,
CH2), 1.07 (s, 3H, CH3), 1.05 (s, 3H, CH3), 0.99-1.02 (m, 1H,
CH2), 0.85-0.88 (m, 1H, CH2). Anal. Calcd. for C27H24N2O4: C,
73.62; H, 5.49; N 6.36. found C, 73.80; H, 5.58; N, 6.27.
5-Cyclopropyl-10-(4-hydroxy-3-nitrophenyl)-7,7-dimethyl-
7,8-dihydro-5H-indeno[1,2-b]quinoline-9,11(6H,10H)-dione
(4c). This compound was obtained according to above general
procedure; ir (potassium bromide): CO 1676, 1647 cm-1; 1H nmr:
ꢀ 10.78 (s, 1H, OH), 7.80 (d, 1H, ArH, J = 7.6 Hz), 7.44-7.49
(m, 2H, ArH), 7.28-7.37 (m, 3H, ArH), 7.01 (d, 1H, ArH, J = 8.8
Hz), 4.74 (s, 1H, CH), 3.59-3.61 (m, 1H, CH), 3.11 (d, 1H, CH2,
J = 17.2 Hz), 2.72 (d, 1H, CH2, J = 17.2 Hz), 2.26 (d, 1H, CH2,
J = 16.4 Hz), 2.23 (d, 1H, CH2, J = 16.4 Hz), 1.29-1.32 (m, 2H,
CH2), 1.05 (s, 6H, CH3), 1.96-0.99 (m, 1H, CH2), 0.78-0.82 (m,
1H, CH2). Anal. Calcd. for C27H24N2O5, C, 71.04; H, 5.30; N,
6.14. found C, 71.20; H, 5.21; N, 6.29.
5-Cyclopropyl-10-(4-fluorophenyl)-7,7-dimethyl-7,8-dihydro-
5H-indeno[1,2-b]quinoline-9,11(6H,10H)-dione (4d). This
compound was obtained according to above general procedure;
ir (potassium bromide): CO 1678, 1649 cm-1; 1H nmr: ꢀ 7.79 (d,
1H, ArH, J = 7.2 Hz), 7.43-7.47 (m, 1H, ArH), 7.30-7.37 (m,
2H, ArH), 7.09-7.12 (m, 2H, ArH), 7.01-7.05 (m, 2H, ArH),
4.78 (s, 1H, CH), 3.57-3.59 (m, 1H, CH), 3.10 (d, 1H, CH2, J =
17.2 Hz), 2.72 (d, 1H, CH2, J = 17.2 Hz), 2.26 (d, 1H, CH2, J =
16.0 Hz), 2.18 (d, 1H, CH2, J = 16.0 Hz), 1.24-1.29 (m, 2H,
CH2), 1.04 (s, 6H, CH3), 0.94-0.97 (m, 1H, CH2), 0.79-0.82 (m,
1H, CH2). Anal. Calcd. for C27H24FNO2: C, 78.43; H, 5.85; N,
3.39. found C, 78.61; H, 5.79; N 3.27.
10-(4-Chlorophenyl)-5-cyclopropyl-7,7-dimethyl-7,8-di-
hydro-5H-indeno[1,2-b]quinoline-9,11(6H,10H)-dione (4e).
This compound was obtained according to above general
procedure; ir (potassium bromide): CO 1684, 1645 cm-1; 1H
nmr: ꢀ 7.80 (d, 1H, ArH, J = 7.2 Hz), 7.43-7.47 (m, 1H, ArH),
7.41 (d, 2H, ArH, J = 8.4 Hz), 7.30-7.35 (m, 2H, ArH), 7.04 (d,
2H, ArH, J = 8.4 Hz), 4.76 (s, 1H, CH), 3.57-3.60 (m, 1H, CH),
3.10 (d, 1H, CH2, J = 17.2 Hz), 2.72 (d, 1H, CH2, J = 17.2 Hz),
2.26 (d, 1H, CH2, J = 16.0 Hz), 2.19 (d, 1H, CH2, J = 16.0 Hz),
1.28-1.30(m, 2H, CH2), 1.05 (s, 6H, CH3), 0.94-0.96 (m, 1H,
CH2), 0.79-0.83(m, 1H, CH2). Anal. Calcd. for C27H24ClNO2: C,
75.43; H, 5.63; N, 3.26. found C, 75.62; H, 5.58; N, 3.38.
10-(4-Bromophenyl)-5-cyclopropyl-7,7-dimethyl-7,8-di-
hydro-5H-indeno[1,2-b]quinoline-9,11(6H,10H)-dione (4f).
This compound was obtained according to above general
procedure; ir (potassium bromide): CO 1684, 1650 cm-1; 1H nmr:
ꢀ 7.80 (d, 1H, ArH, J = 7.6 Hz) 7.43-7.47 (m, 1H, ArH), 7.41 (d,
2H, ArH, J = 8.4 Hz), 7.30-7.35 (m, 2H, ArH), 7.04 (d, 2H,
ArH, J = 8.0 Hz), 4.76 (s, 1H, CH), 3.57-3.59 (m, 1H, CH), 3.10
(d, 1H, CH2, J = 17.2 Hz), 2.72 (d, 1H, CH2, J = 17.2 Hz), 2.26
(d, 1H, CH2, J = 16.0 Hz), 2.19 (d, 1H, CH2, J = 16.0 Hz), 1.28-
1.29 (m, 2H, CH2), 1.04 (s, 6H, CH3), 0.94-0.99 (m, 1H, CH2),
0.79-0.81 (m, 1H, CH2). Anal. Calcd. for C27H24BrNO2: C,
68.36; H, 5.10; N, 2.95. found C, 68.49; H, 5.01; N, 3.02.
5-Cyclopropyl-7,7-dimethyl-10-phenyl-7,8-dihydro-5H-
indeno[1,2-b]quinoline-9,11(6H,10H)-dione (4g). This
compound was obtained according to above general procedure;
ir (potassium bromide): CO 1679, 1644 cm-1; 1H nmr: ꢀ 7.78-
7.82 (m, 1H, ArH), 7.42-7.46 (m, 1H, ArH), 7.29-7.36 (m, 2H,
ArH), 7.19-7.23 (m, 2H, ArH), 7.07-7.12 (m, 3H, ArH), 4.78 (s,
1H, CH), 3.58-3.60 (m, 1H, CH), 3.12 (d, 1H, CH2, J = 17.2 Hz),
2.72 (d, 1H, CH2, J = 17.2 Hz), 2.26 (d, 1H, CH2, J = 16.0 Hz),
2.19 (d, 1H, CH2, J = 16.0 Hz), 1.24-1.31 (m, 2H, CH2), 1.05 (s,
The structures of all the synthesized compounds were
established on the basis of their spectroscopic data. The
IR spectrum of compound 4h showed strong absorptions
1
at 1686 and 1634 cm-1 due to C=O groups. The H NMR
spectrum of 4h showed a singlet at ꢀ 2.19 due to CH3
(3H), and a singlet at ꢀ 4.74 due to CH, and a singlet at ꢀ
1.04 due to CH3 (6H). Furthermore, the structure of 4ꢀ
(Figure 1) [14] were established by an X-ray.
In conclusion, we have disclosed a facile method that
offers a simple and efficient route for the one-pot, three-
component synthesis of highly functionalized indeno[1,2-
b]quinolin derivatives of potential biological importance
in good yields. Particularly valuable features of this
method included the broad substrate scope, high yield, as
well as simple workup procedure. Most importantly, the
series of indeno[1,2-b]quinolin derivatives may prove to
be biological interest and provide new classes of
biological active compounds for biomedical screening.
EXPERIMENTAL
IR spectra were recorded on a TENSOR 27 spectrometer in
KBr. 1H NMR spectra were measured on
a DPX 400
spectrometer operating at 400 MHz, using DMSO-d6 as solvent
and TMS as internal standard. Elemental analyses were
determined by using a Perkin-Elmer 240c elemental analysis
instrument. X-ray crystallographic analysis was performed with
a Siemens SMART CCD and a Semens P4 diffractometer.
General Procedure for the synthesis of 5-cyclopropyl-10-
aryl-7,7-dimethyl-7,8-dihydro-5H-indeno[1,2-b]quinoline-9,
11(6H,10 H)-diones (4a-4k) and 5-cyclopropyl-10-aryl-7,8-
dihydro-5H-indeno[1,2-b]quinoline-9,11(6H,10H)-diones (4l-
4q). A solution of the appropriate aromatic aldehyde (1 mmol),
1,3-indanedione (1 mmol), enaminones (1 mmol) and actetic acid
(5 mL) was introduced into a 25 mL round-bottom flask, heated in
120~140°C oil bath under reflux for 2-4 hour. The reaction
mixture was cooled to room temperature, then poured into water
(50 mL), filtered to give the crude product, which was further
purified by recrystallization from 95%EtOH. All the products (4a-
4q) were characterized by IR, 1H NMR and elemental analysis.
5-Cyclopropyl-7,7-dimethyl-10-(4-nitrophenyl)-7,8-dihydro-
5H-indeno[1,2-b]quinoline-9,11(6H,10H)-dione (4a). This
compound was obtained according to above general procedure;
ir (potassium bromide): CO 1677, 1647 cm-1; 1H nmr: ꢀ 8.10 (d,
2H, ArH, J = 8.4 Hz), 7.83 (d, 1H, ArH, J = 7.6 Hz), 7.46-7.48
(m, 2H, ArH), 7.36 (d, 2H, ArH, J = 8.4 Hz), 7.32 (d, 1H, ArH, J
= 7.6 Hz), 4.62 (s, 1H, CH), 3.59-3.62 (m, 1H, CH), 3.12 (d, 1H,
CH2, J = 17.2 Hz), 2.75 (d, 1H, CH2, J = 17.2 Hz), 2.27 (d, 1H,
CH2, J = 16.0 Hz), 2.20 (d, 1H, CH2, J = 16.0 Hz), 1.26-1.32(m,
2H, CH2), 1.05 (s, 6H, CH3), 0.86-1.02 (m, 2H, CH2). Anal.
Calcd. for C27H24N2O4: C, 73.62; H, 5.49; N, 6.36. found C,
73.81; H, 5.43; N, 6.51.
5-Cyclopropyl-7,7-dimethyl-10-(3-nitrophenyl)-7,8-dihydro-
5H-indeno[1,2-b]quinoline-9,11(6H,10H)-dione (4b). This
compound was obtained according to above general procedure;
ir (potassium bromide): C=O 1680, 1631 cm-1; 1H nmr: ꢀ 7.99 (d,
1H, ArH, J = 7.6 Hz), 7.82-7.85 (m, 2H, ArH), 7.54-7.57 (m,
2H, ArH), 7.45-7.49 (m, 1H, ArH), 7.31-7.38 (m, 2H, ArH),
4.90 (s, 1H, CH), 3.62-3.64 (m, 1H, CH), 3.14 (d, 1H, CH2, J =

1204
Y. Chen, S. Tu, B. Jiang, F. Shi
Vol 44
6H, CH3), 0.89-0.94 (m, 1H, CH2), 0.79-0.82 (m, 1H, CH2).
Anal. Calcd. for C27H25NO2: C, 82.00; H, 6.37; N, 3.54. found C,
82.18; H, 6.33; N, 3.72.ꢀ
2.00-2.03 (m, 2H, CH2), 1.26-1.30(m, 2H, CH2), 0.90-1.00 (m,
2H, CH2). Anal. Calcd. for C25H20N2O4: C, 72.80; H, 4.89; N,
6.79. found C, 72.65; H, 4.93; N, 6.70.
5-Cyclopropyl-10-(4-nitrophenyl)-7,8-dihydro-5H-indeno-
[1,2-b]quinoline-9,11(6H,10H)-dione (4m). This compound
was obtained according to above general procedure; ir
5-Cyclopropyl-7,7-dimethyl-10-p-tolyl-7,8-dihydro-5H-
indeno[1,2-b]quinoline-9,11(6H,10H)-dione (4h). This
compound was obtained according to above general procedure;
ir (potassium bromide): CO 1686, 1634 cm-1; 1H nmr: ꢀ 7.78 (d,
1H, ArH, J = 7.2 Hz), 7.42-7.45 (m, 1H, ArH), 7.28-7.35 (m,
2H, ArH), 7.01 (d, 2H, ArH, J = 8.0 Hz), 6.95 (d, 2H, ArH, J =
7.6 Hz), 4.74 (s, 1H, CH), 3.57-3.59 (m, 1H, CH), 3.10 (d, 1H,
CH2, J = 17.2 Hz), 2.70 (d, 1H, CH2, J = 17.2 Hz), 2.23-2.27(m,
1H, CH2), 2.19 (s, 3H, CH3), 2.16- 2.18(m, 1H, CH2), 1.25-1.32
(m, 2H, CH2), 1.04 (s, 6H, CH3), 0.86-0.91 (m, 1H, CH2), 0.76-
0.79 (m, 1H, CH2). Anal. Calcd. for C28H27NO2: C, 82.12; H,
6.65; N, 3.42. found C, 81.98; H, 6.69; N, 3.28.
10-(benzo[d][1,3]dioxol-5-yl)-5-cyclopropyl-7,7-dimethyl-
7,8-dihydro-5H-indeno[1,2-b]quinoline-9,11(6H,10H)-dione
(4i).ꢀ This compound was obtained according to above general
procedure; ir (potassium bromide): CO 1678, 1647 cm-1; 1H nmr:
ꢀ 7.78 (d, 1H, ArH, J = 7.2 Hz), 7.42-7.46 (m, 1H, ArH), 7.30-
7.36 (m, 2H, ArH), 6.73 (d, 1H, ArH, J = 7.6 Hz), 6.59 (s, 1H,
ArH ), 6.50-6.53 (m, 1H, ArH), 5.92 (s, 2H, CH2), 4.71 (s, 1H,
CH), 3.57-3.60 (m, 1H, CH), 3.12 (d, 1H, CH2, J = 17.2 Hz),
2.70 (d, 1H, CH2, J = 17.2 Hz), 2.28 (d, 1H, CH2, J = 16.0 Hz),
2.18 (d, 1H, CH2, J = 16.0 Hz), 1.23-1.32 (m, 2H, CH2), 1.06 (s,
3H, CH3), 1.04 (s, 3H, CH3), 0.89-0.92 (m, 1H, CH2), 0.76-0.79
(m, 1H, CH2). Anal. Calcd. for C28H25NO4: C, 76.52; H, 5.73; N,
3.19. found C, 76.36; H, 5.68; N, 3.33.ꢀ
5-Cyclopropyl-10-(4-methoxyphenyl)-7,7-dimethyl-7,8-
dihydro-5H-indeno[1,2-b]quinoline-9,11(6H,10H)-dione (4j).
This compound was obtained according to above general
procedure; ir (potassium bromide): CO 1683, 1632 cm-1; 1H nmr:
ꢀ 7.78 (d, 1H, ArH, J = 7.6 Hz), 7.46-7.42(m, 1H, ArH), 7.35-
7.28 (m, 2H, ArH), 6.98 (d, 2H, ArH, J = 8.0 Hz), 6.77 (d, 2H,
ArH, J = 8.0 Hz), 4.72 (s, 1H, CH), 3.66 (s, 3H, OCH3), 3.55-
3.57 (m, 1H, CH), 3.10 (d, 1H, CH2, J = 17.2 Hz), 2.70 (d, 1H,
CH2, J = 17.2 Hz), 2.30 (d, 1H, CH2, J = 16.4 Hz), 2.18 (d, 1H,
CH2, J = 16.4 Hz), 1.30-1.29 (m, 2H, CH2), 1.05 (s, 6H, CH3),
0.93-0.91 (m, 1H, CH2), 0.80-0.77 (m, 1H, CH2). Anal. Calcd.
for C28H27NO3: C, 79.03; H, 6.40; N, 3.29. found C, 78.89; H,
6.49; N, 3.23.
5-Cyclopropyl-10-(3,4-dimethoxyphenyl)-7,7-dimethyl-7,8-
dihydro-5H-indeno[1,2-b]quinoline-9,11(6H,10H)-dione (4k).ꢀ
This compound was obtained according to above general
procedure; ir (potassium bromide): CO 1687, 1633 cm-1; 1H nmr:
ꢀ 7.78 (d, 1H, ArH, J = 7.6 Hz), 7.42-7.46 (m, 1H, ArH), 7.31-
7.34 (m, 2H, ArH), 6.78 (d, 1H, J = 8.0 Hz, ArH), 6.69 (d, 2H, J
= 8.0 Hz, ArH), 4.71 (s, 1H, CH), 3.66 (s, 6H, OCH3), 3.57-
3.62(m, 1H, CH), 3.14 (d, 1H, CH2, J = 17.2 Hz), 2.71 (d, 1H,
CH2, J = 17.6 Hz), 2.26 (d, 1H, CH2, J = 16.0 Hz), 2.19 (d, 1H,
CH2, J = 16.0 Hz), 1.24-1.31 (m, 2H, CH2), 1.06 (s, 6H, CH3),
0.90-0.95 (m, 1H, CH2), 0.76-0.79 (m, 1H, CH2). Anal. Calcd.
for C29H29NO4: C, 76.46; H, 6.42; N, 3.07. found C, 76.29; H,
6.37; N, 3.19.ꢀ
1
(potassium bromide): CO 1681, 1633 cm-1; cm-1; H nmr: ꢀ 8.09
(d, 2H, ArH, J = 8.4 Hz), 7.82 (d, 1H, ArH, J = 7.6 Hz), 7.44-
7.47 (m, 1H, ArH), 7.37 (d, 2H, ArH, J = 8.4 Hz), 7.31-7.34 (m,
2H, ArH), 4.91 (s, 1H, CH), 3.58-3.61 (m, 1H, CH), 3.14-3.20
(m, 1H, CH2), 2.85-2.98 (m, 1H, CH2), 2.28-2.36(m, 2H, CH2),
1.92-2.01 (m, 2H, CH2), 1.23-1.30 (m, 2H, CH2), 0.92-1.00 (m,
2H, CH2). Anal. Calcd. for C25H20N2O4: C, 72.80; H, 4.89; N,
6.79. found C, 72.62; H, 4.92; N, 6.65.
5-Cyclopropyl-10-(4-hydroxy-3-nitrophenyl)-7,8-dihydro-5H-
indeno[1,2-b]quinoline-9,11(6H,10H)-dione (4n). This compound
was obtained according to above general procedure; ir
(potassium bromide): CO 1681, 1630 cm-1; 1H nmr: ꢀ 10.77 (s,
1H, OH), 7.80 (d, 1H, ArH, J = 7.2 Hz), 7.44-7.49 (m, 2H,
ArH), 7.28-7.37 (m, 3H, ArH), 7.00 (d, 1H, ArH, J = 8.4 Hz),
4.74 (s, 1H, CH), 3.59-3.62 (m, 1H, CH), 3.12-3.20 (m, 1H,
CH2), 2.83-2.88 (m, 1H, CH2), 2.31-2.35 (m, 2H, CH2), 1.99-
2.02 (m, 2H, CH2), 1.24-1.28 (m, 2H, CH2), 0.85-0.98 (m, 2H,
CH2). Anal. Calcd. for C25H20N2O5: C, 70.08; H, 4.71; N, 6.54.
found C, 70.25; H, 4.68; N, 6.40.
5-Cyclopropyl-10-(4-fluorophenyl)-7,8-dihydro-5H-indeno-
[1,2-b]quinoline-9,11(6H,10H)-dione (4o). This compound was
obtained according to above general procedure; ir (potassium
1
bromide): CO 1680, 1632 cm-1; H nmr: ꢀ 7.79 (d, 1H, ArH, J =
7.2 Hz), 7.42-7.46 (m, 1H, ArH), 7.29-7.36 (m, 2H, ArH), 7.08-
7.12 (m, 2H, ArH), 7.00-7.04 (m, 2H, ArH), 4.78 (s, 1H, CH),
3.57-3.60 (m, 1H, CH), 3.13-3.21 (m, 1H, CH2), 2.83-2.87 (m,
1H, CH2), 2.30-2.35 (m, 2H, CH2), 1.99-2.02 (m, 2H, CH2),
1.25-1.27 (m, 2H, CH2), 0.85-0.94 (m, 2H, CH2). Anal. Calcd.
for C25H20FNO2: C, 77.90; H, 5.23; N, 3.63. found C, 77.72; H,
5.08; N, 3.69.
5-Cyclopropyl-10-(4-methoxyphenyl)-7,8-dihydro-5H-indeno
[1,2-b]quinoline-9,11(6H,10H)-dione (4p). This compound was
obtained according to above general procedure; ir (potassium
bromide): CO 1682, 1642 cm-1; 1H nmr: ꢀ 7.77 (d, 1H, ArH, J =
7.6 Hz), 7.41-7.45 (m, 1H, ArH), 7.28-7.35 (m, 2H, ArH), 6.98
(d, 2H, ArH, J = 8.4 Hz), 6.76 (d, 2H, ArH, J = 8.4 Hz), 4.72 (s,
1H, CH), 3.66 (s, 3H, OCH3), 3.56-3.59 (m, 1H, CH), 3.14-3.18
(m, 1H, CH2), 2.80-2.87 (m, 1H, CH2), 2.29-2.34 (m, 2H, CH2),
1.98-2.01 (m, 2H, CH2), 1.20-1.33 (m, 2H, CH2), 0.82-0.92 (m,
2H, CH2). Anal. Calcd. for C26H23NO3: C, 78.57; H, 5.83; N,
3.52. found C, 78.72; H 5.76, N, 3.58.
5-Cyclopropyl-10-p-tolyl-7,8-dihydro-5H-indeno[1,2-b]quin-
oline-9,11(6H,10H)-dione (4q). This compound was obtained
according to above general procedure; ir (potassium bromide):
1
CO 1661, 1645 cm-1; H nmr: ꢀ 7.77 (d, 1H, ArH, J = 7.2 Hz),
7.41-7.45 (m, 1H, ArH), 7.28-7.35 (m, 2H, ArH), 7.00 (d, 2H,
ArH, J = 8.0 Hz), 6.96 (d, 2H, ArH, J = 8.0 Hz), 4.75 (s, 1H,
CH), 3.56-3.59 (m, 1H, CH), 3.13-3.19 (m, 1H, CH2), 2.80-2.87
(m, 1H, CH2), 2.19 (s, 3H, CH3), 2.29-2.34 (m, 2H, CH2), 1.92-
2.01 (m, 2H, CH2), 1.22-1.30 (m, 2H, CH2), 0.81-0.90 (m, 2H,
CH2). Anal. Calcd. for C26H23NO2: C, 81.86; H, 6.08; N, 3.67.
found C, 81.72; H, 6.01; N. 3.75.
General Procedure for the synthesis of 2-(4-bromo-
benzylidene)-2H-indene -1,3-dione (5). A solution of the p-
bromobenzaldehyde 1f, 1,3-indanedione 2 and acetic acid (5
mL) was introduced into aꢀ 25 mLꢀ round-bottom flask, heated
5-Cyclopropyl-10-(3-nitrophenyl)-7,8-dihydro-5H-indeno
[1,2-b]quinoline-9,11(6H,10H)-dione (4l). This compound was
obtained according to above general procedure; ir (potassium
bromide): CO 1686, 1647 cm-1; 1H nmr: ꢀ 7.99 (d, 1H, ArH, J =
7.6 Hz), 7.86 (s, 1H, ArH), 7.83(d, 1H, ArH, J =7.6 Hz ), 7.53-
7.57 (m, 2H, ArH), 7.44-7.48 (m, 1H, ArH), 7.31-7.38 (m, 2H,
ArH), 4.90 (s, 1H, CH), 3.62-3.64 (m, 1H, CH), 3.15-3.22 (m,
1H, CH2), 2.85-2.92 (m, 1H, CH2), 2.33-2.36 (m, 2H, CH2),

Sep-Oct 2007
Facile Three-component One-pot Synthesis of
1205
Indeno[1,2-b]quinolin-9,11(6H,10H)-dione Derivatives
[4] Deady, L. W.; Desneves, J.; Kaye, A. J.; Finlay, G. J.;
Baguley, B. C.; Denny, A. W. Bioorg. Med. Chem. 2000, 8, 977.
[5] Brooks, J. R.; Berman, C.; Hichens, M.; Primka, R. L.;
Reynolds, G. F.; Rasmusson, G. H. Proc. Soc. Exp. Biol. Med. 1982,
169, 67.
[6] Rampa, A.; Bisi, A.; Belluti, F.; Gobbi, S.; Valenti, P.;
Andrisano, V.; Cavrini, V.; Cavalli, A.; Recanatini, M. Bioorg. Med.
Chem. 2000, 8, 497.
[7] Venugopalan, B.; Bapat, C. P.; Desouza, E. P.; Desouza,
N. J. Indian J. Chem. Sect. B. 1992, 31B, 35.
[8] Deady, L. W.; Kaye, A. J.; Finlay, G. J.; Baguley, B. C.;
Denny, W. A. J. Med. Chem. 1997, 40, 2040.
[9] Deady, L. W.; Desneves, J.; Kaye, A. J.; Finlay, G. J.;
Baguley, B. C.; Denny. W. A. Bioorg. Med. Chem. 2001, 9, 445.
[10] Bu, X.; Deady. L. W. Synth. Common. 1999, 29, 4223.
[11] Lu, X. L.; Petersen, J. L.; Wang. K. K. Org. Lett. 2003, 5,
3277.
at 120 °C under reflux for half an hour. The reaction mixture
was cooled to room temperature, and then poured into water (50
mL). The solid product was collected by filtration, washed with
water and EtOH (95%), and subsequently dried and
recrystallization from EtOH (95%) to give the pour product 5f in
92% yield. mp: 176-178 °C; ir (potassium bromide): CO 1714,
C=C 1676 cm-1; 1Hnmr: ꢀ 8.45 (d, 2H, ArH, J = 8.4 Hz), 8.02-
8.04 (m, 2H, ArH), 7.97-7.99 (m, 2H, ArH), 7.85 (s, 1H,
CH), 7.81 (d, 2H, ArH, J = 8.4 Hz). Anal. Calcd. for
C16H9BrO2: C, 61.37; H, 2.90. found C, 61.52; H, 2.81.
Acknowledgement. We thank for the National Natural
Science Foundation of China (No. 20672090), the Nature
Science Foundation of the Jiangsu Province (No. BK2006033),
the Foundation of Qinglan Project (No. QL200512) and Dean
Foundation of Xuzhou Education College (No. 2006HX03) the
financial support.
[12] Stankevich, E. I.; Vanags, G. Latvijas PSR Zinatnu
Akademijas Vestis, Kimijas Serija. 1962, 2. 283
[13] Stankevich, E. I.; Vanags, G. Zh. Obshch. Khimii 1962,
32, 1146.
REFERENCES AND NOTES
[14] The single-crystal growth was carried out in ethanol and
DMF at room temperature. X-ray crystallographic analysis was
performed with a Siemens SMART CCD and a Siemens P4
diffractometer. Crystal data for 4d: C27H24FNO2, red, crystal
dimension 0.38 x 0.36 x 0.17 mm, Monoclinic, a= 14.138(3), b =
8.952(2), c =17.140(3) Å, ꢁ = 90°, ꢂ = 102.253(3)°, ꢃ = 90°, V =
2119.9(8) Å3, Mr = 413.47, Z = 4, Dc = 1.296 g/cm3, ꢄ = 0.71073 Å,
μ (Mokꢁ) = 0.087 mm-1, F(000) = 872, S = 1.041, R1 = 0.0425, wR2
= 0.0905.
[1] Anzini, M.; Cappelli, A.; Vomero, S.; Cagnotto, A.;
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[2] Quraishi, A. M.; Thakur, V. R.; Dhawan, S. N. Indian J.
Chem. Sect. B 1989, 28B, 891.
[3] Yamato M.; Takeuchi Y.; Hashigaki K.; Ikeda Y.; Chang,
M. C.; Takeuchi, K.; Matsushima M.; Tsuruo, T.; Tashiro T.;
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