A simple and catalyst-free three-component method for the synthesis of spiro[indenopyrazolopyridine indoline]diones and spiro[indenopyridopyrimidine indoline]triones

Article abstract of DOI:10.1016/j.crci.2010.10.001

An efficient, simple and catalyst-free synthesis of spiro[indeno[1,2-b] pyrazolo[4,3-e]pyridine indoline]diones and spiro[acenaphthylene-indeno[1,2-b] pyrazolo[4,3-e]pyridine]diones by the three-component reaction of 1,3-indandione, pyrazol-5-amines and isatins or acenaphthylene-1,2-dione in refluxing ethanol is reported. Reaction of 2,6-diaminopyrimidin-4(3H)-one with 1,3-indandione and isatins resulted in the formation of 1H-spiro[indeno[1,2-b] pyrido[2,3-d]pyrimidine-5,3′-indoline]-2′,4,6(11H)-triones.

Full text of DOI:10.1016/j.crci.2010.10.001

C. R. Chimie 14 (2011) 556–562
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Full paper/Memoire
A simple and catalyst-free three-component method for the synthesis of
spiro[indenopyrazolopyridine indoline]diones and
spiro[indenopyridopyrimidine indoline]triones
*
Ghazaleh Imani Shakibaei, Afsaneh Feiz, Ayoob Bazgir
Department of Chemistry, Shahid Beheshti University, G.C, 1983963113 Tehran, Iran
A B S T R A C T
A R T I C L E I N F O
Article history:
An efficient, simple and catalyst-free synthesis of spiro[indeno[1,2-b]pyrazolo[4,3-
e]pyridine indoline]diones and spiro[acenaphthylene-indeno[1,2-b]pyrazolo[4,3-e]pyr-
idine]diones by the three-component reaction of 1,3-indandione, pyrazol-5-amines and
isatins or acenaphthylene-1,2-dione in refluxing ethanol is reported. Reaction of 2,6-
diaminopyrimidin-4(3H)-one with 1,3-indandione and isatins resulted in the formation of
1H-spiro[indeno[1,2-b]pyrido[2,3-d]pyrimidine-5,30-indoline]-20,4,6(11H)-triones.
ß 2010 Acade´mie des sciences. Published by Elsevier Masson SAS. All rights reserved.
Received 5 July 2010
Accepted after revision 4 October 2010
Available online 11 November 2010
Keywords:
Isatin
Spirooxindole
Amino pyrazole
Spiroindenopyrazolopyridine indoline
1. Introduction
fumigatus, have been identified as novel inhibitors of
microtubule assembly [5d], and pteropodine and isopter-
In the past few years, combinatorial methods using
multi-component reactions (MCRs) have been closely
examined as a fast and convenient solution for the
synthesis of diverse classes of compounds [1]. MCRs,
defined as one-pot reactions in which at least three
molecule groups join through covalent bonds, have been
steadily gaining importance in synthetic organic chemistry
[1,2]. In the current work, we have elaborated a new MCR
which gives wide access to annulated indenopyrazolopyr-
idine joined to oxindole units through a spiro junction
production.
Indole and indoline fragments are important moieties
of a large number of natural biologically active compounds
[3], and some indolines, spiro-annulated with heterocycles
in the 3-position, have shown high biological activity [4].
The spirooxindole system is the core structure of many
pharmacological agents and natural alkaloids [5]. For
example, spirotryprostatin A and B, two natural alkaloids
isolated from the fermentation broth of Aspergillus
opodine have been shown to modulate the function of
muscarinic serotonin receptors (Fig. 1) [5a]. Indenone-
fused heterocycles represent important biological and
medicinal scaffolds. The indenopyridine skeleton is pres-
ent in the 4-azafluorenone group of alkaloids, represented
by its simplest member onychnine (Fig. 1) [6]. Indenopyr-
azoles I and indenopyridazines II have been investigated as
cyclin-dependent kinase [7] and selective monoamine
oxidase B (MAO-B) [8] inhibitors, respectively. Indenopyr-
idines III exhibit cytotoxic [9a], phosphodiesterase inhibi-
tory [9b], adenosine A2A receptor antagonistic [9c],
antiinflammatory/antiallergic [9d], coronary dilating [9e]
and calcium modulating activities [9f]. These compounds
have also been investigated for the treatment of hyper-
lipoproteinemia and arteriosclerosis [9g] as well as
neurodegenerative diseases [9h].
As part of our program aimed at developing new
methodologies for the preparation of heterocyclic com-
pounds [10], very recently, we have reported the synthesis
of spiro[diindenopyridine indoline]triones [11]. Herein, we
describe an efficient and catalyst-free synthetic approach
to spiro[indeno[1,2-b]pyrazolo[4,3-e]pyridine indoline]-
diones and spiro[indeno[1,2-b]pyrido[2,3-d]pyrimidine-
* Corresponding author.
E-mail address: a_bazgir@sbu.ac.ir (A. Bazgir).
1631-0748/$ – see front matter ß 2010 Acade´mie des sciences. Published by Elsevier Masson SAS. All rights reserved.
doi:10.1016/j.crci.2010.10.001

[()TD$FIG]
G. Imani Shakibaei et al. / C. R. Chimie 14 (2011) 556–562
557
Figure 1. Representatives of important spirooxindoles and indenone-fused heterocycles.
[()TD$FIG]
synthesis of spirooxindole annulated indenopyrazolopyr-
idine. The reactions in ethanol under catalyst-free are
considerably safe, nontoxic, environmentally friendly, and
inexpensive. The absence of catalyst for the reaction allows
avoiding the use of moisture-sensitive and heavy metal-
containing Lewis acids. This method is simple and
convenient and would be applicable for the synthesis of
different types of spiroindoline-pyrazolopyridopyrimidine
derivatives. In addition, the workup of these very clean
reactions involves only a filtration and simple washing
step with EtOH. Using this simple purification protocol the
desired products are obtained in high purity.
Scheme 1.
5,30-indoline]-20,4,6(11H)-triones based on
a one-pot
methodology.
As expected, when the isatin 3 was replaced by
acenaphthylene-1,2-dione 5, 10-aryl-30-phenyl-10H,2H-
spiro[acenaphthylene-1,40-indeno[1,2-b]pyrazolo[4,3-
2. Results and discussion
We found that a mixture of 1,3-indandione 1, pyrazol-
5-amines 2 and isatins 3 in the absence of any catalyst in
refluxing ethanol, afforded spiro[indeno[1,2-b]pyra-
zolo[4,3-e]pyridine indoline]diones 4 in good yields for
2 h (Scheme 1).
To obtain spirooxindole annulated indenopyrazolopyr-
idine, we used four pyrazol-5-amines 2a-d and a wide
diversity of isatins 3a-l, substituted both in aromatic
nucleus and at N-1. In this method, twenty-four new
compounds 4a-x were selectively synthesized by the one-
pot, three-component condensation of 1,3-indandione 1,
1H-pyrazol-5-amines 2 and isatins 3 in good yields
without using any catalyst. The results are summarized
in Table 1.
Recently, we have reported several isatin based three
components reactions for the synthesis of spirooxindole in
the presence of p-TSA as a catalyst [12]. Herein, we used
p-TSA as a catalyst in the reaction but we did not observe
the significant effect of catalyst on the yields and reaction
times. In the previous work the catalyst had a significant
effect on the reaction but it must be emphasized that the
substrate used was also different from the present work.
Thus, meaningful comparison (structural etc.) is not
straightforward. To the best of our knowledge, this new
procedure provides the first example of a catalyst-free
Table 1
Synthesis of spiro[indoline-pyrazolopyridopyrimidine] derivatives 4.
Product 4
Ar
X
R
Yield (%)a
a
b
c
C6H5
H
H
85
87
91
80
92
75
76
73
84
85
87
82
91
93
94
89
87
80
91
88
80
82
91
88
C6H5
Br
NO2
Me
F
H
C6H5
H
d
e
f
C6H5
H
C6H5
H
C6H5
H
Me
Et
PhCH2
Me
Et
Me
Et
H
g
h
i
C6H5
H
C6H5
H
C6H5
Br
Br
NO2
NO2
H
j
C6H5
k
l
C6H5
C6H5
m
n
o
p
q
r
4-NO2-C6H4
4-NO2-C6H4
4-NO2-C6H4
4-NO2-C6H4
4-NO2-C6H4
4-MeO-C6H4
4-MeO-C6H4
4-MeO-C6H4
4-Br-C6H4
4-Br-C6H4
4-Br-C6H4
4-Br-C6H4
Br
NO2
H
H
H
Me
Et
H
H
H
s
NO2
H
H
t
Et
H
u
v
w
x
H
Br
NO2
H
H
H
Me
a
Isolated yields

[()TD$FIG]
558
G. Imani Shakibaei et al. / C. R. Chimie 14 (2011) 556–562
O
O
Ph
N
O
O
O
O
Ph
+
EtOH (Reflux)
2 h
+
N
Ar
N
N
NH2
H
N
Ar
Ar= C6H5
Ar= 4-NO2-C6H4
6a 88%
6c 89%
1
2
5
Scheme 2.
[()TD$FIG]
Scheme 3.
e]pyridine]-2,50(100H)diones 6 were obtained in good
yields under the same reaction conditions (Scheme 2).
To further explore the potential of this protocol for
spirooxindole synthesis, we investigated the reaction of
1,3-indandione 1 and isatin 3 with 2,6-diaminopyrimidin-
4(3H)-one 7 and obtained 2-amino-1H-spiro[indeno[1,2-
b]pyrido[2,3-d]pyrimidine-5,30-indoline]-20,4,6(11H)-
triones 8a-j in 73–82% yields under the same reaction
conditions (Scheme 3).
4. Experimental
4.1. Materials and techniques
Melting points were measured on an Elecrtothermal
9100 apparatus and are uncorrected. 1H and 13C NMR
spectra were recorded on a BRUKER DRX-300 AVANCE
spectrometer at 300.13 and 75.47 MHz, respectively. 1H
and 13C NMR spectra were obtained on solutions in DMSO-
d6 using TMS as internal standard. Due to very low
solubility of the products 4u-x, 8d,e and 8g-i we cannot
report the 13C NMR data for these products. IR spectra were
recorded using an FTIR apparatus. Elemental analyses were
performed using a Heraeus CHN-O-Rapid analyzer.
Compounds 4,
6 and 8 are stable solids whose
structures were established by IR, 1H, and 13C NMR
spectroscopy and elemental analysis.
3. Conclusions
The chemicals used in this work were obtained from
Fluka and Merck and were used without purification.
In conclusion, we have described a facile, catalyst-free
and three-component method for the synthesis of spir-
o[indenopyrazolopyridine indoline]diones, spiro[ace-
4.2. General procedure for preparation of
spiro[indenopyrazolopyridine indoline]diones(4),
spiro[acenaphthylene-1,40-indenopyrazolopyridine]diones
(6) and spiro[indenopyridopyrimidine indoline]triones (7)
naphthylene-indenopyrazolopyridine]diones
and
spiro[indenopyridopyrimidine indoline]triones in ethanol
using readily available starting materials. Prominent
among the advantages of this new method are operational
simplicity, good yields in short reaction times and easy
work-up procedures employed.
A mixture of 1,3-indandione 1 (1 mmol), 1,3-diphenyl-
1H-pyrazol-5-amine 2 or 2,6-diaminopyrimidin-4(3H)-

G. Imani Shakibaei et al. / C. R. Chimie 14 (2011) 556–562
559
one 7 (1 mmol) and isatin 3 or acenaphthylene-1,2-dione 5
(1 mmol) in refluxing ethanol (5 mL) was stirred for 2 h.
After completion of the reaction confirmed by TLC (eluent:
EtOAc/n-hexane, 2:1), the reaction mixture was cooled to
room temperature. Then, the precipitated product was
filtered and washed with water (10 mL) and methanol
(5 mL) to afford the pure product.
128.6, 130.1, 130.9, 132.2, 132.9, 134.1, 136.6, 138.0, 138.2,
138.6, 139.5, 150.1, 157.0, 179.0, 189.4. Anal. Calcd for
C32H19FN4O2: C, 75.28; H, 3.75; N, 10.97% Found: C, 75.15;
H, 3.82; N, 11.04.
10-Methyl-1,3-diphenyl-1H-spiro[indeno[1,2-b]pyra-
zolo[4,3-e]pyridine-4,30-indoline] -20,5(10H)-dione (4f).
Orange powder (yield 75%); m.p. > 300 8C. IR (KBr) (nmax
/
cmꢀ1): 3164, 1685, 1622. 1H NMR (300 MHz, DMSO-d6): dH
(ppm) 2.87 (3H, s, NCH3), 6.72–7.83 (18H, m, H-Ar), 11.30
(1H, s, NH). 13C NMR (75 MHz, DMSO-d6): dC (ppm) 26.4,
47.2, 103.3, 106.5, 108.5, 120.7, 121.2, 123.0, 124.5, 124.9,
128.0, 128.4, 128.6, 128.8, 130.1, 130.9, 132.2, 132.8, 134.1,
135.7, 136.7, 138.2, 139.3, 143.4, 150.1, 157.0, 177.2, 189.4.
Anal. Calcd for C33H22N4O2: C, 78.25; H, 4.38; N, 11.06%
Found: C, 78.15; H, 4.30; N, 10.96.
4.3. Spectral data
1,3-diphenyl-1H-spiro[indeno[1,2-b]pyrazolo [4,3-
e]pyridine-4,30-indoline]-20,5(10H) -dione (4a): orange
powder (yield 85%). m.p. > 300 8C. IR (KBr) (n
max/cmꢀ1):
3435, 3164, 1680, 1669.1H NMR (300 MHz, DMSO-d6): dH
(ppm) 6.70–7.84 (18H, m, H-Ar), 10.32 (1H, s, NH), 11.22
(1H, s, NH).13C NMR (75 MHz, DMSO-d6): dC (ppm) 47.8,
103.1, 106.9, 109.7, 120.7, 121.1, 122.2, 124.9, 126.0, 128.1,
128.5, 128.7, 130.1, 130.9, 132.2, 133.0, 134.1, 136.6, 136.7,
138.2, 139.4, 142.4, 150.2, 156.7, 178.8, 189.5. Anal. Calcd
for C32H20N4O2: C, 78.03; H, 4.09; N, 11.38%. Found: C,
77.92; H, 4.01; N, 11.30%.
10-Ethyl-1,3-diphenyl-1H-spiro[indeno[1,2-b]pyra-
zolo[4,3-e]pyridine-4,30-indoline]-20,5(10H)-dione (4 g).
Orange powder (yield 76%); m.p. > 300 8C. IR (KBr) (nmax
/
cmꢀ1): 3174, 1685, 1622. 1HNMR (300 MHz, DMSO-d6): dH
3
(ppm) 0.87 (3H, t, JHH = 6.9 Hz, CH3), 3.42–3.52 (2H, m,
CH2), 6.70–7.85 (18H, m, H-Ar), 11.27 (1H, s, NH). 13C NMR
50-Bromo-1,3-diphenyl-1H-spiro[indeno[1,2-b]pyra-
zolo[4,3-e]pyridine-4,30-indoline] -20,5(10H)-dione (4b).
(75 MHz, DMSO-d6): dC (ppm) 12.3, 34.7, 47.3, 103.0, 106.7,
108.6, 120.8, 121.1, 122.8, 124.8, 124.9, 128.1, 128.5, 128.6,
128.9, 130.1, 130.9, 132.2, 133.0, 134.1, 136.1, 136.6, 138.2,
139.4, 142.9, 150.1, 156.8, 176.6, 189.4. Anal. Calcd for
Orange powder (yield 87%); m.p. > 300 8C. IR (KBr) (nmax
cmꢀ1): 3461, 3195, 1701, 1674. 1H NMR (300 MHz, DMSO-
d6): H (ppm) 6.61–7.84 (17H, m, H-Ar), 10.46 (1H, s, NH),
11.30 (1H, s, NH). 13C NMR (75 MHz, DMSO-d6):
C (ppm)
/
d
C34H24N4O2: C, 78.44; H, 4.65; N, 10.76% Found: C, 78.35;
d
H, 4.59; N, 10.69.
47.9, 102.5, 106.1, 111.6, 113.9, 120.8, 121.2, 125.0, 127.6,
128.2, 128.5, 128.6, 128.7, 130.0, 131.0, 131.4, 132.2, 132.9,
134.1, 136.6, 138.2, 138.8, 139.5, 141.7, 150.1, 157.0, 178.6,
189.4. Anal. Calcd for C32H19BrN4O2: C, 67.26; H, 3.35; N,
9.80. Found: C, 67.25; H, 3.44; N, 9.72.
50-Nitro-1,3-diphenyl-1H-spiro[indeno[1,2-b]pyra-
zolo[4,3-e]pyridine-4,30-indoline]-20,5(10H)-dione (4c).
10-Benzyl-1,3-diphenyl-1H-spiro[indeno[1,2-b]pyra-
zolo[4,3-e]pyridine-4,30-indoline]
-20,5(10H)-dione
(4 h). Orange powder (yield 73%); m.p. > 300 8C. IR
(KBr) (
max/cmꢀ1): 3174, 1701, 1690. 1H NMR (300 MHz,
DMSO-d6):
H (ppm), 4.18 and 4.90 (2H, ABq, 2JHH = 15.2 Hz,
n
d
CH2), 6.47–7.85 (24H, m, H-Ar), 11.36 (1H, s, NH). 13C NMR
(75 MHz, DMSO-d6): dC (ppm) 44.0, 47.4, 103.2, 106.3,
109.2, 120.9, 121.2, 123.1, 124.7, 124.9, 127.4, 127.5, 128.1,
128.5, 128.9, 130.1, 132.3, 132.7, 134.1, 135.7, 136.3, 136.6,
138.2, 142.7, 150.2, 157.2, 177.6, 189.6. Anal. Calcd for
Orange powder (yield 91%); m.p. > 300 8C. IR (KBr) (nmax
cmꢀ1): 3482, 3153, 1680, 1627. 1H NMR (300 MHz, DMSO-
d6): H (ppm) 6.81–8.08 (17H, m, H-Ar), 11.06 (1H, s, NH),
11.44 (1H, s, NH). 13C NMR (75 MHz, DMSO-d6):
C (ppm)
/
d
d
C39H26N4O2: C, 80.39; H, 4.50; N, 9.62% Found: C, 80.50; H,
47.7, 102.1, 105.3, 109.7, 120.5, 120.9, 121.5, 125.1, 126.1,
128.2, 128.5, 128.7, 130.0, 131.1, 132.3, 132.7, 134.0, 136.5,
137.1, 138.1, 139.6, 142.9, 148.9, 150.1, 157.4, 179.6, 189.4.
Anal. Calcd for C32H19N5O4: C, 71.50; H, 3.56; N, 13.03%
Found: C, 71.59; H, 3.49; N, 12.96.
50-Methyl-1,3-diphenyl-1H-spiro[indeno[1,2-b]pyra-
zolo[4,3-e]pyridine-4,30-indoline] -20,5(10H)-dione (4d).
4.58; N, 9.55.
50-Bromo-10-methyl-1,3-diphenyl-1H-spiro[in-
deno[1,2-b]pyrazolo[4,3-e]pyridine-4,30-indoline]-
20,5(10H)-dione (4i). Orange powder (yield 84%);
m.p. > 300 8C. IR (KBr) (
n
max/cmꢀ1): 3169, 1695, 1622.
H (ppm) 2.87 (3H, s, NCH3),
1H NMR (300 MHz, DMSO-d6):
d
6.76–7.87 (17H, m, H-Ar) 11.37 (1H, s, NH). 13C NMR
(75 MHz, DMSO-d6): dC (ppm) 26.6, 47.3, 102.7, 105.7,
110.4, 114.7, 120.8, 121.4, 125.0, 127.3, 128.1, 128.4, 128.7,
130.0, 131.0, 131.5, 132.3, 132.7, 134.1, 136.6, 137.7, 138.1,
139.4, 142.8, 150.0, 157.3, 176.9, 189.4. Anal. Calcd for
Orange powder (yield 80%); m.p. > 300 8C. IR (KBr) (nmax
cmꢀ1): 3540, 3148, 1695, 1680. 1H NMR (300 MHz, DMSO-
d6): H (ppm) 2.19 (3H, s, CH3), 6.58–7.81 (17H, m, H-Ar),
10.21 (1H, s, NH), 11.20 (1H, s, NH). 13C NMR (75 MHz,
DMSO-d6): C (ppm) 21.1, 47.8, 103.1, 107.1, 109.5, 120.7,
/
d
d
C33H21BrN4O2: C, 67.70; H, 3.62; N, 9.57% Found: C, 67.61;
121.0, 124.9, 125.3, 128.0, 128.5, 129.0, 130.1, 131.1, 132.2,
133.1, 134.1, 136.6, 136.9, 138.2, 139.4, 139.4, 140.0, 150.1,
156.6, 178.7, 189.5. Anal. Calcd for C33H22N4O2: C, 78.25;
H, 4.38; N, 11.06% Found: C, 78.11; H, 4.32; N, 10.96.
50-Fluoro-1,3-diphenyl-1H-spiro[indeno[1,2-b]pyra-
zolo[4,3-e]pyridine-4,30-indoline] -20,5(10H)-dione (4e).
H, 3.56; N, 9.50.
50-Bromo-10-ethyl-1,3-diphenyl-1H-spiro[in-
deno[1,2-b]pyrazolo[4,3-e]pyridine-4,30-indoline]-
20,5(10H)-dione (4j). Orange powder (yield 85%);
m.p. > 300 8C. IR (KBr) (n
max/cmꢀ1): 3169, 1715, 1685.
1H NMR (300 MHz, DMSO-d6): dH (ppm) 0.86 (3H, t,
3JHH = 6.9 Hz, CH3), 3.42–3.52 (2H, m, CH2), 6.74–7.84 (17H,
m, H-Ar) 11.35 (1H, s, NH). 13C NMR (75 MHz, DMSO-d6):
Orange powder (yield 92%); m.p. > 300 8C. IR (KBr) (nmax
cmꢀ1): 3420, 3231, 1721, 1701. 1H NMR (300 MHz, DMSO-
d6): H (ppm) 6.63–7.85 (17H, m, H-Ar), 10.32 (1H, s, NH),
11.25 (1H, s, NH). 13C NMR (75 MHz, DMSO-d6):
C (ppm)
48.3, 102.7, 106.2, 110.3, 120.8, 121.2, 124.9, 128.1, 128.5,
/
d
dC (ppm) 12.2, 34.8, 47.4, 102.3, 105.9, 110.6, 114.5, 120.8,
121.3, 125.0, 127.6, 128.2, 128.4, 128.6, 128.7, 130.0, 131.0,
131.6, 132.3, 132.8, 134.0, 136.6, 138.2, 139.6, 142.2, 150.0,
d

560
G. Imani Shakibaei et al. / C. R. Chimie 14 (2011) 556–562
157.1, 176.3, 189.4. Anal. Calcd for C34H23BrN4O2: C, 68.12;
H, 3.87; N, 9.35% Found: C, 68.23; H, 3.79; N, 9.46.
10-Methyl-50-nitro-1,3-diphenyl-1H-spiro[in-
m.p. > 300 8C. IR (KBr) (
n
max/cmꢀ1): 3143, 1680, 1612.
H (ppm) 2.87 (3H, s, CH3),
1H NMR (300 MHz, DMSO-d6):
d
6.73–8.51 (17H, m, H-Ar), 11.38 (1H, s, NH). 13C NMR
(75 MHz, DMSO-d6): dC (ppm) 26.5, 47.1, 104.3, 106.7,
108.5, 120.9, 121.0, 123.0, 124.5, 125.0, 125.5, 128.1, 128.4,
128.8, 129.0, 131.0, 132.2, 132.4, 133.8, 135.3, 136.6, 143.1,
143.4, 146.5, 151.6, 177.0. Anal. Calcd for C33H21N5O4: C,
71.86; H, 3.84; N, 12.70% Found: C, 71.73; H, 3.75; N, 12.60.
10-Ethyl-1-(4-nitrophenyl)-3-phenyl-1H-spiro[in-
deno[1,2-b]pyrazolo[4,3-e]pyridine-
deno[1,2-b]pyrazolo[4,3-e]pyridine-4,30-indoline]-
20,5(10H)-dione (4k). Orange powder (yield 87%);
m.p. > 300 8C. IR (KBr) (
n
max/cmꢀ1): 3174, 1701, 1685.
H (ppm) 2.98 (3H, s, NCH3),
1H NMR (300 MHz, DMSO-d6):
d
6.76–7.14 (17H, m, H-Ar) 11.51 (1H, s, NH). 13C NMR
(75 MHz, DMSO-d6): dC (ppm) 26.9, 47.0, 102.2, 108.7,
120.1, 120.9, 121.6, 125.1, 126.1, 128.2, 128.5, 128.7, 130.0,
131.1, 132.5, 136.2, 136.6, 138.1, 143.4, 149.3, 150.1, 178.1.
Anal. Calcd for C33H21N5O4: C, 71.86; H, 3.84; N, 12.70%
Found: C, 71.94; H, 3.76; N, 12.62.
4,30-indoline]-20,5(10H)-dione (4q). Orange powder
(yield 87%); m.p. > 300 8C. IR (KBr) (
n
max/cmꢀ1): 3153,
H (ppm) 0.87
1695, 1690. 1H NMR (300 MHz, DMSO-d6):
d
10-Ethyl-50-nitro-1,3-diphenyl-1H-spiro[indeno[1,2-
b]pyrazolo[4,3-e]pyridine-4,30-indoline]-20,5(10H)-
dione (4l). Orange powder (yield 82%); m.p. > 300 8C. IR
(3H,t, 3JHH = 6.3 Hz, CH3), 3.41–3.54 (2H, m, CH2), 6.70–8.51
(17H, m, H-Ar), 11.35 (1H, s, NH). 13C NMR (75 MHz,
DMSO-d6): dC (ppm) 12.2, 34.7, 47.3, 103.9, 107.0, 108.7,
121.0, 122.9, 124.8, 125.0, 125.5, 128.2, 128.4, 128.8, 129.0,
131.0, 132.4, 133.8, 135.7, 136.5, 140.1, 142.8, 143.1, 146.5,
151.6, 156.8, 176.5, 189.5. Anal. Calcd for C34H23N5O4: C,
72.20; H, 4.10; N, 12.38% Found: C, 72.10; H, 4.17; N, 12.31.
1-(4-Methoxyphenyl)-3-phenyl-1H-spiro[in-
(KBr) (
DMSO-d6):
CH2), 6.74–8.21 (17H, m, H-Ar) 11.48 (1H, s, NH). 13C NMR
(75 MHz, DMSO-d6): C (ppm) 12.2, 35.3, 47.2, 101.9, 105.2,
n
max/cmꢀ1): 3174, 1695, 1664. 1H NMR (300 MHz,
d
H (ppm) 0.91 (3H, bs, CH3), 3.48–3.61 (2H, m,
d
108.8, 120.3, 120.9, 121.6, 125.1, 126.2, 128.3, 128.5, 128.7,
130.0, 131.1, 132.3, 132.6, 134.0, 136.6, 138.1, 139.7, 143.3,
148.9, 150.1, 157.4, 177.6, 189.4. Anal. Calcd for
deno[1,2-b]pyrazolo[4,3-e]pyridine-4,30-indoline]-
20,5(10H)-dione (4r). Orange powder (yield 80%);
C34H23N5O4: C, 72.20; H, 4.10; N, 12.38% Found: C,
m.p. > 300 8C. IR (KBr) (
n
max/cmꢀ1): 3430, 3148, 1690,
H (ppm) 3.87 (3H, s,
72.09; H, 4.03; N, 12.49.
1674. 1H NMR (300 MHz, DMSO-d6):
d
1-(4-Nitrophenyl)-3-phenyl-1H-spiro[indeno[1,2-
b]pyrazolo[4,3-e]pyridine-4,30-indoline]-20,5(10H)-
dione (4m). Orange powder (yield 91%); m.p. > 300 8C. IR
OCH3), 6.68–7.84 (17H, m, H-Ar), 10.32 (1H, s, NH), 11.12
(1H, s, NH). 13C NMR (75 MHz, DMSO-d6): dC (ppm) 47.9,
56.1, 102.6, 106.8, 109.7, 115.1, 120.7, 121.0, 122.2, 124.8,
126.8, 128.0, 128.4, 128.5, 128.7, 130.8, 131.1, 132.1, 133.2,
134.2, 136.6, 136.8, 139.5, 142.4, 149.6, 156.7, 159.6, 178.9,
189.4. Anal. Calcd for C33H22N4O3: C, 75.85; H, 4.24; N,
10.72% Found: C, 75.77; H, 4.16; N, 10.84.
(KBr) (
(300 MHz, DMSO-d6):
10.37 (1H, s, NH), 11.30 (1H, s, NH). 13C NMR (75 MHz,
DMSO-d6): C (ppm) 47.8, 94.6, 104.1, 107.1, 109.8, 120.9,
n
max/cmꢀ1): 3409, 3137, 1711, 1706. 1H NMR
d
H (ppm) 6.66–8.49 (17H, m, H-Ar),
d
122.3, 125.0, 125.5, 128.1, 128.5, 128.8, 131.0, 132.3, 132.4,
132.8, 136.4, 136.5, 140.0, 142.3, 143.1, 146.5, 151.7, 156.7,
178.7, 189.5. Anal. Calcd for C32H19N5O4: C, 71.50; H, 3.56;
N, 13.03% Found: C, 71.63; H, 3.64; N, 13.11.
1-(4-Methoxyphenyl)-50-nitro-3-phenyl-1H-spir-
o[indeno[1,2-b]pyrazolo[4,3-e]pyridine-4,30-indoline]-
20,5(10H)-dione (4s). Orange powder (yield 91%);
m.p. > 300 8C. IR (KBr) (
n
max/cmꢀ1): 3420, 3263, 1690,
H (ppm) 3.88 (3H, s,
50-Bromo-1-(4-nitrophenyl)-3-phenyl-1H-spiro[in-
deno[1,2-b]pyrazolo[4,3-e]pyridine-4,30-indoline]-
20,5(10H)-dione (4n). Orange powder (yield 93%);
1680. 1H NMR (300 MHz, DMSO-d6):
d
OCH3), 6.81–8.08 (16H, m, H-Ar), 11.05 (1H, s, NH), 11.34
(1H, s, NH). 13C NMR (75 MHz, DMSO-d6): dC (ppm) 47.8,
56.1, 101.6, 105.2, 109.7, 115.1, 120.5, 120.9, 121.4, 126.1,
127.0, 128.2, 128.5, 128.6, 131.0, 131.1, 132.3, 132.8, 134.1,
136.5, 137.2, 139.7, 142.9, 148.9, 149.6, 157.4, 159.7, 179.7,
18.4. Anal. Calcd for C33H21N5O5: C, 69.84; H, 3.73; N,
12.34% Found: C, 69.71; H, 3.67; N, 12.25.
m.p. > 300 8C. IR (KBr) (n
max/cmꢀ1): 3425, 3174, 1706,
1674. 1H NMR (300 MHz, DMSO-d6): dH (ppm) 6.61–8.51
(16H, m, H-Ar), 10.53 (1H, s, NH), 11.40 (1H, s, NH). 13C
NMR (75 MHz, DMSO-d6): dC (ppm) 47.9, 103.5, 106.4,
111.6, 113.9, 121.0, 125.2, 125.5, 127.8, 128.2, 128.4, 128.9,
131.1, 131.6, 132.3, 133.9, 136.5, 138.5, 140.2, 141.6, 143.1,
146.6, 151.5, 157.0, 178.4. Anal. Calcd for C32H18BrN5O4: C,
62.35; H, 2.94; N, 11.36% Found: C, 62.21; H, 2.83; N, 11.43.
50-Nitro-1-(4-nitrophenyl)-3-phenyl-1H-spiro[in-
10-Ethyl-1-(4-methoxyphenyl)-3-phenyl-1H-spir-
o[indeno[1,2-b]pyrazolo[4,3-e] pyridine-4,30-indoline]-
20,5(10H)-dione (4t). Orange powder (yield 88%);
m.p. > 300 8C. IR (KBr) (n
max/cmꢀ1): 3174, 1674, 1612.
deno[1,2-b]pyrazolo[4,3-e]pyridine-4,30-indoline]-
20,5(10H)-dione (4o). Orange powder (yield 94%);
1H NMR (300 MHz, DMSO-d6): dH (ppm) 0.86 (3H, t,
3JHH = 6.9 Hz, CH3), 3.44–3.57 (2H, m, CH2), 3.87 (3H, s,
OCH3), 6.68–7.91 (17H, m, H-Ar), 11.17 (1H, s, NH). 13C
m.p. > 300 8C. IR (KBr) (
1701, 1685. 1H NMR (300 MHz, DMSO-d6):
8.52 (16H, m, H-Ar), 11.09 (1H, s, NH), 11.51 (1H, s, NH). 13
n
max/cmꢀ1): 3331, 2918, 2840,
H (ppm) 6.81–
d
NMR (75 MHz, DMSO-d6): dC (ppm) 12.3, 34.6, 47.3, 56.1,
C
102.4, 106.6, 108.6, 115.1, 120.7, 121.1, 122.7, 123.1, 124.7,
126.8, 128.1, 128.3, 128.4, 128.8, 130.8, 131.1, 132.1, 133.1,
134.1, 136.1, 136.6, 139.5, 142.9, 149.5, 156.7, 159.6, 174.1,
176.6, 189.4. Anal. Calcd for C35H26N4O3: C, 76.35; H, 4.76;
N, 10.18% Found: C, 76.22; H, 4.69; N, 10.25.
NMR (75 MHz, DMSO-d6): dC (ppm) 47.7, 103.1, 109.8,
120.7, 121.1, 121.3, 125.4, 125.5, 126.2, 128.3, 128.5, 129.0,
131.2, 132.2, 132.5, 136.5, 136.8, 142.9, 143.1, 146.7, 148.8,
151.5, 179.4. Anal. Calcd for C32H18N6O6: C, 65.98; H, 3.11;
N, 14.43% Found: C, 65.90; H, 3.05; N, 14.38.
1-(4-Bromophenyl)-3-phenyl-1H-spiro[indeno[1,2-
b]pyrazolo[4,3-e]pyridine-4,30-indoline]-20,5(10H)-
dione (4u). Orange powder (yield 80%); m.p. > 300 8C. IR
10-Methyl-1-(4-nitrophenyl)-3-phenyl-1H-spiro[in-
deno[1,2-b]pyrazolo[4,3-e]pyridine
20,5(10H)-dione (4p). Orange powder (yield 89%);
-4,30-indoline]-
(KBr) (n
max/cmꢀ1): 3440, 3143, 1691, 1621. 1H NMR

G. Imani Shakibaei et al. / C. R. Chimie 14 (2011) 556–562
561
(300 MHz, DMSO-d6):
10.13 (1H, s, NH), 10.91 (1H, s, NH). Anal. Calcd for
32H19BrN4O2: C, 67.26; H, 3.35; N, 9.80;% Found: C, 67.35;
d
H (ppm) 6.66–7.83 (17H, m, H-Ar),
2-Amino-50-bromo-1H-spiro[indeno[1,2-b]pyr-
ido[2,3-d]pyrimidine-5,30-indoline]-20,4,6(11H)-triones
C
(8b). Light orange Powder (yield 77%); m.p. > 300 8C. IR
H, 3.28; N, 9.74.
(KBr) (n
max/cmꢀ1): 3456, 3184, 1706, 1648, 1633. 1H NMR
50-Bromo-1-(4-bromophenyl)-3-phenyl-1H-spir-
o[indeno[1,2-b]pyrazolo[4,3-e]pyridine -4,30-indoline]-
20,5(10H)-dione (4v). Orange Powder (yield 82%);
(300 MHz, DMSO-d6): dH (ppm) 6.57–7.82 (9H, m, H-Ar,
NH2), 10.41 (1H, s, NH), 10.62 (1H, s, NH), 11.01 (1H, s, NH).
13C NMR (75 MHz, DMSO-d6): dC (ppm) 48.0, 92.6, 105.6,
110.8, 113.1, 120.8, 126.3, 130.5, 131.0, 132.3, 133.6, 136.3,
138.9, 142.5, 154.9, 155.7, 156.5, 161.1, 179.2, 189.6. Anal.
Calcd for C21H12BrN5O3: C, 54.56; H, 2.62; N, 15.15%;.
Found: C, 54.46; H, 2.68; N, 15.09.
2-Amino-50-nitro-1H-spiro[indeno[1,2-b]pyrido[2,3-
d]pyrimidine-5,30-indoline]-20,4,6(11H)-triones (8c). Or-
ange Powder (yield 81%); m.p. > 300 8C. IR (KBr) (nmax/
m.p. > 300 8C. IR (KBr) (n
max/cmꢀ1): 3425, 3130, 1687,
1629. 1H NMR (300 MHz, DMSO-d6): dH (ppm) 6.68–7.98
(16H, m, H-Ar), 11.02 (1H, s, NH), 11.30 (1H, s, NH). Anal.
Calcd for C32H18Br2N4O2: C, 59.10; H, 2.79; N, 8.62;%
Found: C, 59.18; H, 2.70; N, 8.68
1-(4-Bromophenyl)-50-nitro-3-phenyl-1H-spiro[in-
deno[1,2-b]pyrazolo[4,3-e]pyridine
20,5(10H)-dione (4w). Orange Powder (yield 91%);
max/cmꢀ1): 3430, 3137, 1685,
-4,30-indoline]-
cmꢀ1): 3649, 3435, 3326, 1716, 1690, 1643. 1H NMR
(300 MHz, DMSO-d6): dH (ppm) 6.64–8.11 (9H, m, H-Ar,
NH2), 10.69 (1H, s, NH), 11.05 (1H, s, NH), 11.16 (1H, s, NH).
13C NMR (75 MHz, DMSO-d6): dC (ppm) Anal. 47.8, 92.0,
104.9, 108.9, 119.0, 120.9, 125.6, 131.1, 132.4, 133.5, 136.3,
137.4, 142.4, 149.8, 155.1, 156.0, 157.0, 161.3, 180.2, 189.6.
Calcd for C21H12N6O5: C, 58.88; H, 2.82; N, 19.62% Found:
C, 58.76; H, 2.90; N, 19.53.
m.p. > 300 8C. IR (KBr) (
n
1627. 1H NMR (300 MHz, DMSO-d6): dH (ppm) 6.69–8.01
(16H, m, H-Ar), 11.07 (1H, s, NH), 11.35 (1H, s, NH). Anal.
Calcd for C32H18BrN5O4: C, 62.35; H, 2.94; N, 11.36;%
Found: C, 62.44; H, 2.99; N, 11.31.
1-(4-Bromophenyl)-10-methyl-3-phenyl-1H-spir-
o[indeno[1,2-b]pyrazolo[4,3-e] pyridine-4,30-indoline]-
20,5(10H)-dione (4x). Orange Powder (yield 88%);
2-Amino-50-methyl-1H-spiro[indeno[1,2-b]pyr-
ido[2,3-d]pyrimidine-5,30-indoline]-20,4,6(11H)-triones
(8d). Light orange Powder (yield 79%); m.p. > 300 8C. IR
m.p. > 300 8C. IR (KBr) (
1H NMR (300 MHz, DMSO-d6):
6.72–7.91 (17H, m, H-Ar), 11.12 (1H, s, NH). Anal. Calcd for
33H21BrN4O2: C, 67.70; H, 3.62; N, 9.57% Found: C, 67.56;
n
max/cmꢀ1): 3420, 1711, 1695.
H (ppm) 2.87 (3H, s, CH3),
d
(KBr) (n
max/cmꢀ1): 3602, 3430, 3383, 1695, 1648, 1627. 1H
C
NMR (300 MHz, DMSO-d6): dH (ppm) 3.14 (3H, s, CH3),
6.56–7.81 (9H, m, H-Ar, NH2), 10.49 (1H, s, NH), 11.00 (1H,
s, NH). Anal. Calcd for C22H15N5O3: C, 66.49; H, 3.80; N,
17.62% Found: C, 66.38; H, 3.73; N, 17.54.
2-Amino-50-fluoro-1H-spiro[indeno[1,2-b]pyr-
ido[2,3-d]pyrimidine-5,30-indoline]-20,4,6(11H)-triones
H, 3.53; N, 9.50.
10,30-diphenyl-10H,2H-spiro[acenaphthylene-1,40-
indeno[1,2-b]pyrazolo[4,3-e]pyridine]-2,50(100H)-dione
(6a). Orange Powder (yield 88%); m.p. > 300 8C. IR (KBr)
(
n
max/cmꢀ1): 3174, 1714, 1690. 1H NMR (300 MHz, DMSO-
d6):
d
H (ppm) 6.36–8.17 (20H, m, H-Ar), 11.36 (1H, s, NH).
C (ppm) 52.5, 104.7, 108.2,
(8e). Red Powder (yield 80%); m.p. > 300 8C. IR (KBr) (nmax/
13C NMR (75 MHz, DMSO-d6):
d
cmꢀ1): 3639, 3514, 3378, 3158, 1789, 1721, 1638. 1H NMR
(300 MHz, DMSO-d6): dH (ppm) 6.55–7.79 (9H, m, H-Ar,
NH2), 10.27 (1H, s, NH), 10.60 (1H, s, NH), 10.99 (1H, s, NH).
Anal. Calcd for C21H12FN5O3: C, 62.84; H, 3.01; N, 17.45%
Found: C, 62.70; H, 3.08; N, 17.53.
120.7, 121.2, 121.4, 121.9, 124.9, 127.3, 128.0, 128.2, 128.6,
128.8, 129.4, 130.0, 130.1, 131.8, 132.3, 133.3, 136.8, 138.2,
141.4, 145.0, 150.3, 157.1, 189.8, 205.2. Anal. Calcd for
C36H21N3O2: C, 81.96; H, 4.01; N, 7.96% Found: C, 81.85; H,
4.07; N, 7.89.
2-Amino-10-methyl-1H-spiro[indeno[1,2-b]pyr-
ido[2,3-d]pyrimidine-5,30-indoline]-20,4,6(11H)-triones
(8f). Orange Powder (yield 78%); m.p. > 300 8C. IR (KBr)
10-(4-nitrophenyl)-30-phenyl-10H,2H-spiro[ace-
naphthylene-1,40-indeno[1,2-b]pyrazolo[4,3-e]pyri-
dine]-2,50(100H)-dione (6b). Orange Powder (yield 89;
(n
max/cmꢀ1): 3382, 3174, 1704, 1648, 1630. 1H NMR
m.p. > 300 8C. IR (KBr) (
n
max/cmꢀ1): 3190, 1685, 1648. 1
H
(300 MHz, DMSO-d6):
dH (ppm) 3.13 (3H, s, CH3). 6.55–7.80
NMR (300 MHz, DMSO-d6): dH (ppm) 6.36–8.52 (19H, m,
H-Ar), 11.42 (1H, s, NH). 13C NMR (75 MHz, DMSO-d6): dC
(ppm) 52.4, 105.7, 108.5, 121.1, 121.6, 12.0, 125.0, 127.4,
128.2, 128.3, 128.8, 129.4, 130.1, 131.0, 131.7, 131.8, 133.2,
136.7, 141.4, 143.2, 143.2, 144.7, 146.5, 151.7, 204.9. Anal.
Calcd for C36H20N4O4: C, 75.52; H, 3.52; N, 9.79% Found: C,
75.40; H, 3.44; N, 9.71.
(9H, m, H-Ar, NH2), 10.48 (1H, s, NH), 10.99 (1H, s, NH). 13
C
NMR (75 MHz, DMSO-d6): dC (ppm) 26.7, 47.2, 107.7,
120.5, 120.6, 122.1, 123.3, 128.0, 130.9, 132.3, 133.5, 135.7,
136.4, 154.9, 155.6, 156.2, 178.0, 189.5. Anal. Calcd for
C22H15N5O3: C, 66.49; H, 3.80; N, 17.62% Found: C, 66.56;
H, 3.85; N, 17.51.
2-Amino-10-ethyl-1H-spiro[indeno[1,2-b]pyr-
ido[2,3-d]pyrimidine-5,30-indoline]-20,4,6(11H)-triones
(8 g). Orange Powder (yield 77%); m.p. > 300 8C. IR (KBr)
2-Amino-1H-spiro[indeno[1,2-b]pyrido[2,3-d]py-
rimidine-5,30-indoline]-20,4,6(11H)-triones (8a). Light
orange powder (yield 82%); m.p. 268–270 8C. IR (KBr)
(n
max/cmꢀ1): 3446, 3336, 1701, 1680, 1648. 1HNMR
(
n
max/cmꢀ1): 3461, 3336, 3195, 1701, 1648, 1627. 1H NMR
(300 MHz, DMSO-d6): dH (ppm) 1.23 (3H, bs, CH3), 3.65–
3.78 (2H, m, CH2), 6.57–7.81 (10H, m, H-Ar, NH2), 10.49 (1H,
s, NH), 10.99 (1H, s, NH). Anal. Calcd for C23H17N5O3: C,
67.15; H, 4.16; N, 17.02% Found: C, 67.01; H, 4.07; N, 16.91.
2-Amino-50-bromo-10-methyl-1H-spiro[indeno[1,2-
b]pyrido[2,3-d]pyrimidine -5,30-indoline]-20,4,6(11H)-
triones (8 h). Light orange Powder (yield 78%);
(300 MHz, DMSO-d6): dH (ppm) 6.50–7.77 (10H, m, H-Ar,
NH2), 10.23 (1H, s, NH), 10.56 (1H, s, NH), 10.92 (1H, s, NH).
13C NMR (75 MHz, DMSO-d6): dC (ppm) 47.7, 93.1, 106.5,
108.8, 120.4, 120.6, 121.4, 123.6, 127.7, 128.6, 130.8, 132.2,
133.6, 136.4, 136.5, 143.0, 154.8, 155.6, 156.1, 161.1, 179.5,
189.6. Anal. Calcd for C21H13N5O3: C, 65.79; H, 3.42; N,
18.27%. Found: C, 65.70; H, 3.37; N, 18.19.
m.p. > 300 8C. IR (KBr) (n
max/cmꢀ1): 3479, 3382, 17014,

562
G. Imani Shakibaei et al. / C. R. Chimie 14 (2011) 556–562
1648, 1630, 1603. 1H NMR (300 MHz, DMSO-d6):
dH (ppm)
[7] D.A. Nugiel, A.-M. Etzkorn, A. Vidwans, P.A. Benfield, M. Boisclair,
C.R. Burton, S. Cox, P.M. Czerniak, D. Doleniak, S.P. Seitz, J. Med. Chem
44 (2001) 1334.
[8] R. Fre´derick, W. Dumont, F. Ooms, L. Aschenbach, C.J. Van der Schyf,
N. Castagnoli, J. Wouters, A.J. Krief, Med. Chem 49 (2006) 3743.
[9] (a) R. Miri, K. Javidnia, B. Hemmateenejad, A. Azarpira, Z. Amirghofran,
Bioorg. Med. Chem 12 (2004) 2529;
3.12 (3H, s, CH3), 6.61–7.81 (9H, m, H-Ar, NH2), 10.53 (1H,
s, NH), 11.07 (1H, s, NH). Anal. Calcd for C22H14BrN5O3: C,
55.48; H, 2.96; N, 14.70% Found: C, 55.40; H, 3.02; N, 14.77.
2-Amino-50-bromo-10-ethyl-1H-spiro[indeno[1,2-
b]pyrido[2,3-d]pyrimidine -5,30-indoline]-20,4,6(11H)-
triones (8i). Yellow Powder (yield 73%); m.p. > 300 8C.
(b) Heintzelman, G. R. Averill K. M.; Dodd, J. H. PCT Int. Appl. WO
2002085894 A1 20021031, (2002);
(c) G.R. Heintzelman, K.M. Averill, J.H. Dodd, K.T. Demarest, Y. Tang,
P.F. Jackson, Pat. Appl. Publ. US 2004082578 A1 20040429 (2004);
(d) K. Cooper, M.J. Fray, P.E. Cross, K. Richardson, Eur. Pat. Appl. EP
299727 A1 19890118 (1989);
(e) Vigante B, Ozols, J. Sileniece, G. Kimenis A. Duburs, G. U. S. S. R. SU,
794006 19810107, (1989);
(f) C. Safak, R. Simsek, Y. Altas, S. Boydag, K. Erol, Boll. Chim. Farm 136
(1997) 665;
IR (KBr) (n
max/cmꢀ1): 3446, 3336, 1701, 1680, 1648. 1H
NMR (300 MHz, DMSO-d6): dH (ppm) 1.19 (3H, bs, CH3),
3.70 (2H, bs, CH2), 6.61–7.81 (9H, m, H-Ar, NH2), 10.51 (1H,
s, NH), 11.04 (1H, s, NH). Anal. Calcd for C23H16BrN5O3: C,
56.34; H, 3.29; N, 14.28% Found: C, 56.23; H, 3.21; N, 14.22.
2-Amino-10-methyl-50-nitro-1H-spiro[indeno[1,2-
b]pyrido[2,3-d]pyrimidine-5,30-indoline]-20,4,6(11H)-
triones (8j). Orange Powder (yield 76%); m.p. 270–272 8C.
(g) A. Brandes, M. Loegers, G. Schmidt, R. Angerbauer, C. Schmeck,
K.-D. Bremm, H. Bischoff, D. Schmidt, Schuhmacher, J. Ger. Offen. DE
19627430 A1 19980115 (1998);
IR (KBr) (
n
max/cmꢀ1): 3566, 3346, 3211, 1701, 1669, 1643.
(h) Heintzelman G. R.; Averill, K. M.; Dodd, J. H.; Demarest, K. T.; Tang
Y.; Jackson, P. F. PCT Int. Appl. WO 2003088963 A1 20031030, 2003..
[10] (a) A. Bazgir, M. Seyyedhamzeh, Z. Yasaei, P. Mirzaei, Tetrahedron Lett
48 (2007) 8790;
1H NMR (300 MHz, DMSO-d6): dH (ppm) 3.25(3H, s, CH3),
6.68–8.19 (10H, m, H-Ar, NH2), 10.65 (1H, s, NH), 11.22
(1H, s, NH). 13C NMR (75 MHz, DMSO-d6):
dC (ppm) 27.32,
47.2, 91.8, 104.7, 107.9, 118.7, 120.9, 121.0, 125.7, 131.2,
132.5, 133.4, 136.2, 136.6, 142.9, 150.7, 155.1, 156.1, 157.1,
161.2, 178.9, 189.6. Anal. Calcd for C22H14N6O5: C, 59.73;
H, 3.19; N, 19.00% Found: C, 59.92; H, 3.11; N, 19.09.
(b) M. Sayyafi, M. Seyyedhamzeh, H.R. Khavasi, A. Bazgir, Tetrahedron
64 (2008) 2375;
(c) M. Dabiri, H. Arvin-Nezhad, H.R. Khavasi, A. Bazgir, J. Heterocycl.
Chem 44 (2007) 1009;
(d) M. Dabiri, S.C. Azimi, H. Arvin-Nezhad, A. Bazgir, Heterocycles 75
(2008) 87;
(e) M. Dabiri, A.S. Delbari, A. Bazgir, Synlett (2007) 821;
(f) M. Dabiri, H. Arvin-Nezhad, H.R. Khavasi, A. Bazgir, Tetrahedron 63
(2007) 1770;
Acknowledgements
(g) M. Dabiri, A.S. Delbari, A. Bazgir, Heterocycles 71 (2007) 543;
(h) R. Ghahremanzadeh, G. Imani Shakibaei, A. Bazgir, Synlett (2008)
1129;
(i) G. Imani Shakibaei, H.R. Khavasi, P. Mirzaei, A. Bazgir, J. Heterocycl.
Chem 45 (2008) 1481;
We gratefully acknowledge financial support from the
Research Council of Shahid Beheshti University.
(j) A. Bazgir, Z. Noroozi Tisseh, P. Mirzaei, Tetrahedron Lett 49 (2008)
5165;
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