An efficient four-component reaction for the synthesis of chromeno[4,3-b]quinolone derivatives

Article abstract of DOI:10.1007/s13738-016-1027-3

Chromenoquinolines have been prepared via an efficient one-pot, multi-component reaction of 4-hydroxy coumarin, aqueous ammonia, dimedone and different aldehydes.

Full text of DOI:10.1007/s13738-016-1027-3

J IRAN CHEM SOC
DOI 10.1007/s13738-016-1027-3
ORIGINAL PAPER
An efficient four‑component reaction for the synthesis
of chromeno[4,3‑b]quinolone derivatives
Azadeh Yahya‑Meymandi1 · Hamideh Nikookar2 · Setareh Moghimi3 ·
Mohammad Mahdavi4 · Loghman Firoozpour3 · Ali Asadipour5 ·
Parviz Rashidi Ranjbar2 · Alireza Foroumadi1,5
Received: 16 July 2016 / Accepted: 5 December 2016
© Iranian Chemical Society 2016
Abstract Chromenoquinolines have been prepared via an
efficient one-pot, multi-component reaction of 4-hydroxy
coumarin, aqueous ammonia, dimedone and different
aldehydes.
products and drugs [1–4]. The advantageous features of
this strategy in the facile preparation of privileged struc-
tures involve the atom economy, convergent character,
diversity-generating potential and formation of several
bonds in a single step. Therefore, this strategy has been
widely employed by different research groups for the one-
pot construction of versatile nitrogen-containing polycyclic
skeletons [5–10].
Keywords Chromenoquinolines · 4-Hydroxy coumarin ·
One pot · Multi-component reaction
Nitrogen-containing multi-cyclic compounds are inter-
esting scaffolds because of their potential in exhibiting
a wide array of bioactivities like DNA intercalators, anti-
plasmodial, antineoplastic, anticancer and antibacterial
[11–17]. Chromenoquinoline, an important subclass of
nitrogen-containing heterocycles, has shown promising
activities [18–20] like anti-inflammatory, anticancer, glu-
cocorticoid modulators, progesterone and 5-HT receptor
antagonist [21–25]. These significant bioactivities are also
reflected in ongoing efforts of synthetic chemists to pre-
pare structurally different chromenoquinolines with hopes
to find new therapeutically active compounds [26–36]. In
this context, developing efficient and simple pathways for
the synthesis of such an important framework from com-
mercially available starting materials is a desirable chal-
lenge. Despite the effectiveness of these methods, in most
of these approaches catalytic systems or synthesized start-
ing materials have to be employed. Thereafter, we decided
to examine the new pathway toward chromenoquinolines
from readily available starting materials and under catalyst-
free condition. In continuation of our program to develop
new and efficient methods for the synthesis of heterocy-
clic compounds [37–43], herein, we envisaged a simple,
four-component reaction for the synthesis of 10,11-
dihydro-10,10-dimethyl-7-substituted-7H-chromeno
[4,3-b]quinoline-6,8(9H,12H)-diones in moderate to good
yields.
Introduction
The multi-component reactions (MCRs) are of consid-
erable interest in organic synthesis since they provide a
rapid access to the important structures, resembling natural
Electronic supplementary material The online version of this
article (doi:10.1007/s13738-016-1027-3) contains supplementary
material, which is available to authorized users.
* Alireza Foroumadi
aforoumadi@yahoo.com
1
Department of Medicinal Chemistry, Faculty of Pharmacy
and Pharmaceutical Sciences Research Center, Tehran
University of Medical Sciences, Tehran, Iran
2
School of Chemistry, College of Science, University
of Tehran, PO Box 14155-6455, Tehran, Iran
3
Drug Design and Development Research Center, Tehran
University of Medical Sciences, Tehran, Iran
4
Endocrinology and Metabolism Research Center,
Endocrinology and Metabolism Clinical Sciences Institute,
Tehran University of Medical Sciences, Tehran, Iran
5
Department of Medicinal Chemistry, Faculty
of Pharmacy and Neuroscience Research Center, Institute
of Neuropharmacology, Kerman University of Medical
Sciences, Kerman, Iran
1 3

J IRAN CHEM SOC
(s, 1H), 2.64 (s, 2H), 2.26 (d, J = 16.0 Hz, 1H), 2.10 (d,
J = 16.0 Hz, 1H), 1.07 (s, 3H), 0.97 (s, 3H). 13C NMR
(125 MHz, DMSO-d6): δ (ppm) 194.5, 160.2, 156.9, 151.9,
149.4, 146.9, 142.0, 131.8, 128.7, 123.9, 122.7, 118.2,
116.7, 114.8, 113.1, 113.0, 110.8, 101.7, 50.1, 34.0, 32.1,
28.9, 26.6. Anal. Calcd. for C24H21NO4: C, 74.40; H, 5.46;
N, 3.62. Found: C, 74.29; H, 5.38; N, 3.74.
Experimental
Melting points were taken on a Kofler hot-stage appara-
tus and are uncorrected. H- and 13C-NMR spectrum was
1
recorded on Bruker FT-500, using TMS as an internal
standard. The elemental analysis was performed with an
Elementar Analysen system GmbH VarioEL CHNS mode.
Mass spectra were determined on an Agilent Technology
(HP) mass spectrometer operating at an ionization potential
of 70 eV. All reagents and solvents were purchased from
Aldrich and Merck and used without any purification.
10,11-Dihydro-7-(2-methoxyphenyl)-10,10-dimethyl-7H-
chromeno[4,3-b]quinoline-6,8(9H,12H)-dione (5c) Pale-
yellow powder (0.27 g, 68%). Mp (°C): 301–303.36 IR
(KBr) 3300, 1695, 1629, 1598, 1474, 1358, 1241, 1189,
1150, 1007, 749, 637. 1H NMR (500 MHz, DMSO-
d6): δ (ppm) 9.62 (s, NH), 8.28 (d, J = 8.0 Hz, 1H),
7.60 (t, J = 7.5 Hz, 1H), 7.43 (t, J = 8.0 Hz, 1H), 7.32
(d, J = 7.5 Hz, 1H), 7.26 (dd, J = 7.5, 1.5 Hz, 1H), 7.08
(t, J = 8.0 Hz, 1H), 6.84 (d, J = 8.0 Hz, 1H), 6.79 (t,
J = 7.5 Hz, 1H), 5.05 (s, 1H), 3.63 (s, 3H), 2.59 (s, 2H),
2.21 (d, J = 16.0 Hz, 1H), 1.98 (d, J = 16.0 Hz, 1H), 1.05
(s, 3H), 0.90 (s, 3H). 13C NMR (125 MHz, DMSO-d6): δ
(ppm) 194.2, 159.9, 157.9, 151.9, 149.8, 142.4, 132.4,
131.5, 127.4, 123.7, 122.6, 119.6, 119.2, 116.6, 113.0,
111.3, 109.2, 100.3, 55.2, 50.2, 32.9, 31.9, 29.2, 25.9. Anal.
Calcd. for C25H23NO4: C, 74.79; H, 5.77; N, 3.49. Found:
C, 74.68; H, 5.92; N, 3.28.
General procedure for the synthesis of chromeno[4,3‑b]
quinoline 5a‑j
A mixture of 4-hydroxy coumarin (1 mmol) and 28–30%
ammonia solution (5 mmol) in n-PrOH (5 mL) was refluxed
for 1 h. Then, aldehyde (1 mmol) and dimedone (1 mmol)
were added, and the reaction was continued at reflux tem-
perature for another 11 h. After this time, the reaction was
cooled down to room temperature. The residue was purified
by column chromatography (petroleum ether/ethyl acetate
10:1).
10,11-Dihydro-10,10-dimethyl-7-phenyl-7H-chromeno
[4,3-b]quinoline-6,8(9H,12H)-dione
(5a) Pale-yellow
powder (0.28 g, 76%). Mp (°C): 290–291.36 IR (KBr) 3213,
3072, 1704, 1630, 1599, 1471, 1360, 1194, 1145, 1023,
1
10,11-Dihydro-7-(4-methoxyphenyl)-10,10-dimethyl-7H-
chromeno[4,3-b]quinoline-6,8(9H,12H)-dione (5d) Pale-
yellow powder (0.29 g, 72%). Mp (°C): 261–263.36 IR
(KBr) 3220, 1689, 1641, 1605, 1508, 1468, 1363, 1257,
1193, 1030, 842, 752. 1H NMR (500 MHz, DMSO-
d6): δ (ppm) 9.65 (s, NH), 8.30 (d, J = 7.5 Hz, 1H),
7.62 (t, J = 8.0 Hz, 1H), 7.43 (t, J = 7.5 Hz, 1H), 7.36
(d, J = 8.0 Hz, 1H), 7.15 (d, J = 7.5 Hz, 2H), 6.77 (d,
J = 7.5 Hz, 2H), 4.90 (s, 1H), 3.66 (s, 3H), 2.66 (s, 2H),
2.26 (d, J = 16.0 Hz, 1H), 2.09 (d, J = 16.0 Hz, 1H), 1.08
(s, 3H), 0.96 (s, 3H). 13C NMR (125 MHz, DMSO-d6): δ
(ppm) 194.6, 160.2, 157.6, 152.0, 149.3, 141.8, 138.1,
131.8, 128.6, 127.9, 124.0, 122.8, 116.7, 113.5, 111.0,
102.1, 54.9, 50.1, 33.4, 32.1, 29.0, 26.5. Anal. Calcd. for
C25H23NO4: C, 74.79; H, 5.77; N, 3.49. Found: C, 74.85;
H, 5.59; N, 3.66.
738, 694. H NMR (500 MHz, DMSO-d6): δ (ppm) 9.70
(s, NH), 8.30 (dd, J = 7.5, 1.0 Hz, 1H), 7.62 (dt, J = 7.5,
1.0 Hz, 1H), 7.43 (t, J = 7.5 Hz, 1H), 7.36 (d, J = 7.5 Hz,
1H), 7.25 (d, J = 7.5 Hz, 2H), 7.21 (t, J = 8.0 Hz, 2H),
7.10 (t, J = 7.0 Hz, 1H), 4.97 (s, 1H), 2.67 (s, 2H), 2.27 (d,
J = 16.5 Hz, 1H), 2.10 (d, J = 16.5 Hz, 1H), 1.08 (s, 3H),
0.95 (s, 3H). 13C NMR (125 MHz, DMSO-d6): δ (ppm)
194.5, 160.1, 152.0, 149.5, 145.7, 142.0, 131.8, 127.6,
126.1, 123.8, 122.8, 116.8, 116.6, 112.9, 110.8, 101.8,
50.1, 34.3, 32.0, 28.9, 26.5. Anal. Calcd. for C24H21NO3: C,
77.61; H, 5.70; N, 3.77. Found: C, 77.53; H, 5.62; N, 3.89.
MS: m/z (%) = 371 ([M]+, 20), 294 (100), 238 (11), 210
(15), 97 (12), 57 (21), 43 (19).
10,11-Dihydro-7-(3-hydroxyphenyl)-10,10-dimethyl-7H-
chromeno[4,3-b]quinoline-6,8(9H,12H)-dione (5b) Pale-
yellow powder (0.27 g, 70%). Mp (°C): 190–192. IR (KBr)
3518, 3320, 1700, 1629, 1461, 1362, 1195, 1150, 1059,
756. 1H NMR (500 MHz, DMSO-d6): δ (ppm) 9.65 (s, NH),
9.08 (s, OH), 8.29 (d, J = 8.0 Hz, 1H), 7.63 (t, J = 7.0 Hz,
1H), 7.43 (t, J = 8.0 Hz, 1H), 7.36 (d, J = 7.0 Hz, 1H),
6.97 (t, J = 8.0 Hz, 1H), 6.68 (d, J = 1.5 Hz, 1H), 6.65
(d, J = 8.0 Hz, 1H), 6.48 (dd, J = 7.5, 1.5 Hz, 1H), 4.90
10,11-Dihydro-7-(3,4,5-trimethoxyphenyl)-10,10-dimethyl-
7H-chromeno[4,3-b]quinoline-6,8(9H,12H)-dione
(5e) Pale-yellow powder (0.32 g, 69%). Mp (°C):
302–303.36 IR (KBr) 3522, 3208, 1678, 1631, 1505,
1
1479, 1363, 1191, 1113, 1010, 764. H NMR (500 MHz,
DMSO-d6): δ (ppm) 9.71 (s, NH), 8.28 (d, J = 8.0 Hz,
1 3

J IRAN CHEM SOC
1H), 7.63 (t, J = 8.5 Hz, 1H), 7.43 (t, J = 8.0 Hz, 1H),
7.36 (d, J = 8.5 Hz, 1H), 6.53 (s, 2H), 4.94 (s, 1H), 3.68
(s, 6H), 3.59 (s, 3H), 2.71 (d, J = 16.5 Hz, 1H), 2.68 (d,
J = 16.5 Hz, 1H), 2.30 (d, J = 16.0 Hz, 1H), 2.13 (d,
J = 16.0 Hz, 1H), 1.11 (s, 3H), 0.97 (s, 3H). 13C NMR
(125 MHz, DMSO-d6): δ (ppm) 194.6, 160.3, 152.4, 151.9,
149.9, 141.8, 141.1, 131.8, 124.0, 122.8, 116.8, 116.6,
113.0, 110.3, 105.2, 101.7, 59.8, 55.6, 50.1, 34.2, 32.0,
29.1, 26.4. Anal. Calcd. for C27H27NO6: C, 70.27; H, 5.90;
N, 3.03. Found: C, 70.09; H, 5.77; N, 2.85.
(d, J = 178 Hz), 152.0, 149.6, 142.1, 142.0, 132.0, 129.5,
124.1, 123.9, 123.0 (d, J = 8 Hz), 116.7 (d, J = 33 Hz),
114.6, 113.0, 110.7, 101.6, 50.0, 33.9, 32.1, 29.0, 26.6.
Anal. Calcd. for C24H20FNO3: C, 74.02; H, 5.18; N, 3.60.
Found: C, 73.88; H, 5.02; N, 3.49.
7-(2-Chlorophenyl)-10,11-dihydro-10,10-dime-
thyl-7H-chromeno[4,3-b]quinoline-6,8(9H,12H)-dione
(5h) Pale-yellow powder (0.30 g, 74%). Mp (°C):
299–301.36 IR (KBr) 3289, 3079, 1707, 1631, 1605, 1508,
1
1472, 1362, 1197, 1147, 1021, 735. H NMR (500 MHz,
10,11-Dihydro-10,10-dimethyl-7-p-tolyl-7H-chromeno
DMSO-d6): δ (ppm) 9.65 (s, NH), 8.30 (d, J = 7.5 Hz,
1H), 7.62 (t, J = 7.5 Hz, 1H), 7.43 (t, J = 7.5 Hz, 1H),
7.38 (d, J = 7.5 Hz, 1H), 7.34 (d, J = 8.0 Hz, 1H), 7.25 (d,
J = 8.0 Hz, 1H), 7.18 (t, J = 7.5 Hz, 1H), 7.11 (t, J = 8.0 Hz,
1H), 5.28 (s, 1H), 2.63 (s, 2H), 2.23 (d, J = 16.0 Hz, 1H),
2.02 (d, J = 16.0 Hz, 1H), 1.07 (s, 3H), 0.94 (s, 3H). 13C
NMR (125 MHz, DMSO-d6): δ (ppm) 194.2, 159.7, 152.0,
149.8, 142.5, 132.0, 129.2, 127.6, 126.4, 124.0, 123.7, 123.0,
122.9, 116.8, 116.6, 112.7, 110.1, 100.9, 50.1, 34.1, 31.8,
29.0, 26.3. Anal. Calcd. for C24H20ClNO3: C, 71.02; H, 4.97;
N, 3.45. Found: C, 70.86; H, 5.11; N, 3.29.
[4,3-b]quinoline-6,8(9H,12H)-dione
(5f) Pale-yellow
powder (0.27 g, 71%). Mp (°C): 331–333.36 IR (KBr):
3215, 1644, 1509, 1471, 1364, 1195, 1043, 844, 762.
1H NMR (500 MHz, DMSO-d6): δ (ppm) 9.63 (s, NH),
8.29 (d, J = 8.0 Hz, 1H), 7.63 (t, J = 7.5 Hz, 1H), 7.43
(t, J = 8.0 Hz, 1H), 7.36 (d, J = 7.5 Hz, 1H), 7.12 (d,
J = 8.0 Hz, 2H), 6.99 (d, J = 8.0 Hz, 2H), 4.91 (s, 1H),
2.65 (s, 2H), 2.25 (d, J = 16.0 Hz, 1H), 2.19 (s, 3H), 2.08
(d, J = 16.0 Hz, 1H), 1.07 (s, 3H), 0.95 (s, 3H). 13C NMR
(125 MHz, DMSO-d6): δ (ppm) 194.5, 160.1, 151.9, 149.3,
142.8, 141.8, 135.1, 131.8, 128.4, 127.5, 123.7, 122.8,
116.7, 113.0, 110.9, 101.9, 50.1, 33.9, 32.0, 28.9, 26.5,
20.4. Anal. Calcd. for C25H23NO3: C, 77.90; H, 6.01; N,
3.63. Found: C, 77.78; H, 5.85; N, 3.57.
10,11-Dihydro-10,10-dimethyl-7-(2-nitrophenyl)-7H-chro
meno[4,3-b]quinoline-6,8(9H,12H)-dione (5i) Pale-yel-
low powder (0.31 g, 75%). Mp (°C): 262–263.36 IR (KBr)
3301, 1700, 1611, 1515, 1475, 1350, 1244, 1196, 1150,
1
7-(4-Fluorophenyl)-10,11-dihydro-10,10-dime-
thyl-7H-chromeno[4,3-b]quinoline-6,8(9H,12H)-dione
(5g) Pale-yellow powder (0.30 g, 77%). Mp (°C): 218–
220.36 IR (KBr) 3470, 3301, 1711, 1631, 1593, 1470,
1024, 739. H NMR (500 MHz, DMSO-d6): δ (ppm) 9.67
(s, NH), 8.32 (d, J = 7.5 Hz, 1H), 7.79 (d, J = 8.0 Hz, 1H),
7.65 (t, J = 7.5 Hz, 1H), 7.54 (t, J = 7.5 Hz, 1H), 7.46-7.40
(m, 2H), 7.39 (d, J = 8.0 Hz, 1H), 7.18 (t, J = 7.5 Hz, 1H),
5.85 (s, 1H), 2.64 (s, 2H), 2.22 (d, J = 16.0 Hz, 1H), 2.02
(d, J = 16.0 Hz, 1H), 1.06 (s, 3H), 0.90 (s, 3H). 13C NMR
(125 MHz, DMSO-d6): δ (ppm) 194.4, 160.4, 151.8, 150.5,
147.8, 146.5, 142.0, 133.8, 132.0, 129.2, 124.0, 123.0,
122.1, 121.3, 116.7, 112.8, 110.0, 100.9, 49.8, 35.0, 31.9,
28.6, 26.5. Anal. Calcd. for C24H20N2O5: C, 69.22; H, 4.84;
N, 6.73. Found: C, 69.07; H, 4.98; N, 6.57.
1
1360, 1194, 1148, 1041, 850, 743. H NMR (500 MHz,
DMSO-d6): δ (ppm) 9.71 (s, NH), 8.31 (d, J = 7.0 Hz,
1H), 7.63 (t, J = 7.5 Hz, 1H), 7.43 (t, J = 7.0 Hz, 1H),
7.38 (d, J = 7.5 Hz, 1H), 7.25-7.23 (m, 2H), 7.04-7.01
(m, 2H), 4.95 (s, 1H), 2.66 (s, 2H), 2.26 (d, J = 16.0 Hz,
1H), 2.09 (d, J = 16.0 Hz, 1H), 1.06 (s, 3H), 0.94 (s, 3H).
13C NMR (125 MHz, DMSO-d6): δ (ppm) 194.6, 161.6
HN
O
O
OH
Ph
n-PrOH
NH3 .H2O + PhCHO
+
+
Reflux
O
O
O
O
O
3a
4
5a
1
2
Scheme 1 Four-component synthesis of chromeno[4,3-b]quinolines
1 3

J IRAN CHEM SOC
Table 1 Optimization of the reaction in different conditions
Table 2 Synthesis of chromenoquinolines using various aldehyde
(Scheme 1)
derivatives
Entry
Solvent
Temp. (°C)
Yield (%)a
1
MeOH
EtOH
Reflux
Reflux
Reflux
Reflux
120 °C
r.t.
32
HN
O
2
51
3
n-PrOH
t-BuOH
–
76
Ar
4
5b
49
O
O
Trace
28
5
6
n-PrOH
n-PrOH
n-PrOH
n-PrOH
7c
8d
9e
Reflux
Reflux
Reflux
55
Compound
Ar
Yield (%)a
49
36
5a
5b
5c
5d
5e
5f
C6H5
76
70
68
72
69
71
77
74
75
79
3-HOC6H4
The reactions were carried out in 5 mL solvent with 1 (1 mmol), 2
(5 mmol) 3a (1 mmol) and 4 (1 mmol) under reflux for 12 h
2-MeOC6H4
4-MeOC6H4
a
b
c
Isolated yields, solvent-free condition was examined, 10 mmol
d
aqueous ammonia was used, 15 mmol aqueous ammonia was used,
3,4,5-triMeOC6H2
4-MeC6H4
and e ammonium acetate (5 mmol) was used
5g
5h
5i
4-FC6H4
10,11-Dihydro-10,10-dimethyl-7-(3-nitrophenyl)-7H-chro
meno[4,3-b]quinoline-6,8(9H,12H)-dione (5j) Pale-yel-
low powder (0.33 g, 79%). Mp (°C): 280–282.36 IR (KBr)
2-ClC6H4
2-O2NC6H4
3-O2NC6H4
5j
1
3215, 1647, 1603, 1510, 1469, 1347, 1189, 1044, 715. H
a
Isolated yields
NMR (500 MHz, DMSO-d6): δ (ppm) 9.82 (s, NH), 8.33
(d, J = 8.0 Hz, 1H), 8.07 (s, 1H), 8.00 (d, J = 7.5 Hz,
1H), 7.73 (d, J = 7.5 Hz, 1H), 7.65 (t, J = 7.5 Hz, 1H),
7.54 (t, J = 7.5 Hz, 1H), 7.46 (t, J = 7.5 Hz, 1H), 7.38
(d, J = 8.0 Hz, 1H), 5.08 (s, 1H), 2.51 (s, 2H), 2.29 (d,
J = 16.0 Hz, 1H), 2.10 (d, J = 16.0 Hz, 1H), 1.10 (s, 3H),
0.96 (s, 3H). 13C NMR (125 MHz, DMSO-d6): δ (ppm)
194.5, 160.1, 152.1, 150.3, 147.6, 147.5, 142.5, 134.5,
132.1, 129.5, 124.1, 123.0, 122.1, 121.3, 116.7, 112.8,
110.0, 100.9, 49.9, 34.9, 32.1, 28.9, 26.4. Anal. Calcd. for
C24H20N2O5: C, 69.22; H, 4.84; N, 6.73. Found: C, 69.46;
H, 4.68; N, 6.58.
the yield of the desired product (Table 1, entries 7–8). This
implied that further increase in the amount of ammonia
has no positive effect on the yield. By employing ammo-
nium acetate as a nitrogen source, the desired product was
obtained in lower yields (Table 1, entry 9).
To survey the generality of the reaction, various aro-
matic aldehydes were reacted under the optimized reac-
tion condition, affording the desired products 5a–j in
moderate to good yields. Both electron-donating and elec-
tron-withdrawing aldehydes were found suitable for this
reaction. The structure of cyclized compounds were con-
1
firmed by IR, H-NMR and 13C-NMR spectroscopy. The
distinguished peak related to H-4 was appeared at 4.90–
5.85 ppm region as a singlet peak. Electron-withdrawing
group led to the appearance of this peak at lower fields
(Table 2).
Results and discussions
In the initial study, we examined the model reaction of
4-hydroxy coumarin 1 (1 mmol), aqueous ammonia 2
(5 mmol), benzaldehyde 3a (1 mmol) and dimedone 4
(1 mmol) in different solvents and various amounts of
ammonia. The results are summarized in Table 1. It was
showed that the best yield of the product 5a was obtained
in refluxing n-propanol (Table 1, entries 1–4). Solvent-free
condition led to the trace amounts of the product (Table 1,
entry 5). To examine the effect of the amount of ammonia,
the reaction was carried out by employing 10 and 15 mmol
of aqueous ammonia. It was observed that raising the
amount of ammonia to twofold–threefold didn’t improve
Conclusion
To conclude, by the one-pot reaction of dimedone, ammonia,
4-hydroxy coumarin and aromatic aldehydes, the correspond-
ing chromeno[4,3-b]quinoline was synthesized in moderate
to good yields. This procedure can be applied to the synthesis
of various 10,11-dihydro-10,10-dimethyl-7H-chromeno[4,3-
b]quinoline-6,8(9H,12H)-diones by employing readily avail-
able starting material in a straightforward one-pot manner.
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Acknowledgements This work was supported and funded by grants
from the research council of Tehran University of Medical Sciences
(TUMS) and Iran National Science Foundation (INSF).
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