One-pot three-component synthesis of novel spiroindenoquinoxalines

Article abstract of DOI:10.1007/s11164-014-1680-z

Numerous new spiroindenoquinoxalines containing pyrano groups were synthesized via a one-pot, three-component reaction of indenoquinoxaline, malononitrile with various α-methylenecarbonyl compounds (β-diketones, pyrazolones) catalyzed by triethylamine.

Full text of DOI:10.1007/s11164-014-1680-z

Res Chem Intermed
DOI 10.1007/s11164-014-1680-z
One-pot three-component synthesis of novel
spiroindenoquinoxalines
Feiran Chen
Yiqun Li
•
Jia Zheng
•
Mingming Huang
•
Received: 14 February 2014 / Accepted: 16 April 2014
Ó Springer Science+Business Media Dordrecht 2014
Abstract Numerous new spiroindenoquinoxalines containing pyrano groups were
synthesized via a one-pot, three-component reaction of indenoquinoxaline, malon-
onitrile with various a-methylenecarbonyl compounds (b-diketones, pyrazolones)
catalyzed by triethylamine.
Keywords Spiroindenoquinoxaline ꢀ Multicomponent reaction ꢀ
Indenoquinoxaline ꢀ Malononitrile ꢀ a-Methylenecarbonyl compound ꢀ
Triethylamine
Introduction
Multicomponent reactions (MCRs), which play an important role in combinatorial
synthesis, have recently attracted attention as a powerful bond-forming tool for
efficient construction of highly complex molecules. Three or more reactants
combine via MCRs to form new products which contain structural units of all the
substrates and have wide structural and functional diversity [1–5]. In the past
decade, numerous MCRs that offer a large variety of important heterocyclic
compounds have been found, receiving considerable attention in recent years [6–9].
As an important class of naturally occurring substances, spiro-compounds show
highly pronounced biological properties [10]. Thus, there have been more and more
reports about synthesis of novel spiroheterocycle compounds, such as spirooxindoles
[11], spiroacenaphthylenes [12], spiropyrrolidine bisoxindoles [13], spiro[indole-
thiazolidinones] [14], and spiro[benzo[c]pyrano[3,2-a]phenazine] derivatives [15,
F. Chen ꢀ J. Zheng ꢀ Y. Li (&)
Department of Chemistry, Jinan University, Guangzhou 510632, China
e-mail: tlyq@jnu.edu.cn
M. Huang
College of Life Science & Technology, Jinan University, Guangzhou 510632, China
123

F. Chen et al.
1
6]. Pyran annulated coumarins have also been found to have a wide spectrum of well-
known biological activities including spasmolytic, anticoagulant, diuretic, anticancer,
etc. [17, 18]. In addition, biological activities of the spiropyran structural system have
been proved as well in recent years [19, 20]. On the other hand, quinoxaline derivatives
have received considerable interest due to their various biological activities. Some of
them have been proved to possess antiviral, antibacterial, antimycobacterial,
anticancer, and antitumor properties [21–25].
Encouraged by the biological activities and applications of the structurally
diverse spiro-compounds with fused heterocyclic systems, we are interested in
developing new spiroheterocycles containing quinoxalines and pyran rings. More
recently, several procedures using AcONH [26], InCl [27, 28], Na CO [29] etc.
4
3
2
3
as catalysts for synthesis of similar spiroindenoquinoxaline derivatives have been
reported in the literature. In continuation of our efforts towards the development of
newer practical MCRs, we report herein the preparation of various novel
spiroindenoquinoxalines catalyzed by Et N under mild condition.
3
Results and discussion
We first synthesized one of the starting materials, indenoquinoxaline 1 (11H-
indeno[1,2-b]quinoxalin-11-one), via the reaction of ninhydrin with 1,2-diamino-
benzene (Scheme 1).
Subsequently, reaction of as-prepared indenoquinoxaline 1, dimedone 2a with
malononitrile 3 was selected as a model to optimize the reaction conditions
(
Table 1). We first examined this reaction in the absence and presence of several
basic and acidic additives under reflux in EtOH. As Table 1 shows, when the
reaction was carried out in the presence of acidic additives or under catalyst-free
condition, the product of Knoevenagel condensation was obtained uniquely
(
Table 1, entries 1–3). When the reaction was carried out in the presence of
0 mol% D,L-proline, imidazole, and N-methylimidazole, no desired product was
3
detected (Table 1, entries 4–6). These results indicated that the catalyst was
essential in the reaction. It was also observed that the reaction could proceed with
low yield when using 0.3 equiv. 1,4-diazabicyclo[2.2.2]octane (DABCO) and
0
.3 equiv. Et N as catalyst (Table 1, entries 7, 8). Increasing the amount of Et N
3 3
from 0.3 equiv. to 1.0 equiv., 2.0 equiv., and 3.0 equiv., the reaction yield rose
from 31 to 70, 81, and 81 %, respectively (Table 1, entries 9–11). Therefore, 2.0
equiv. of the Et N catalyst was enough to push the reaction to completion. Then,
3
various solvents including EtOH, MeOH, H O, CH CN, dimethylformamide
2
3
(
DMF), and polyethylene glycol (PEG-400) were examined, and the results showed
that EtOH was the most effective medium for this transformation. After carefully
screening the reaction conditions, the optimum results were obtained when equiv. of
indenoquinoxaline 1 with dimedone 2a and malononitrile 3 in EtOH were treated
with 3.0 equiv. of Et N catalyst at reflux (Table 1, entry 11).
3
To widen the scope of the multicomponent reaction described above, indeno-
quinoxaline 1, various a-methylenecarbonyl compounds
2
(b-diketones,
1
23

Synthesis of novel spiroindenoquinoxalines
O
O
NH2
EtOH
OH
OH
N
+
Reflux
NH2
N
O
Scheme 1 Synthesis of 11H-indeno[1,2-b]quinoxalin-11-one
Table 1 Optimization of reaction conditions
a
Entry
Solvent
Catalyst
Yield (%)
1
2
3
4
5
6
7
8
9
EtOH
EtOH
EtOH
EtOH
EtOH
EtOH
EtOH
EtOH
EtOH
EtOH
EtOH
None
Knoevenagel product
TsOH, 30 mol%
Knoevenagel product
CAN, 30 mol%
Knoevenagel product
D,L-Proline, 30 mol%
Imidazole, 30 mol%
N-Methylimidazole, 30 mol%
DABCO, 30 mol%
Incomplete
Incomplete
Incomplete
28
Et
3
Et
3
Et
3
Et
3
Et
3
Et
3
Et
3
Et
3
Et
3
N, 30 mol%
N, 1.0 equiv.
N, 2.0 equiv.
N, 3.0 equiv.
N, 2.0 equiv.
N, 2.0 equiv.
N, 2.0 equiv.
N, 2.0 equiv.
N, 2.0 equiv.
31
70
1
1
1
1
1
1
1
0
1
2
3
4
5
6
81
81
b
H
2
O
Incomplete
CH
3
CN
48
b
b
PEG-400
DMF
70
62
MeOH
Incomplete
The reaction was run with indenoquinoxaline 1 (1 mmol), dimedone 2a (1 mmol), and malononitrile 3
(1 mmol) in solvent (10 ml) at reflux
a
Isolated yields
b
The reaction was carried out at 80 °C
pyrazolones), and malononitrile 3 were chosen for synthesis of novel spirohetero-
cycles under the optimized reaction condition (Scheme 2).
Various a-methylenecarbonyl compounds were used to afford the corresponding
products. The reactions with both 1,3-diketones and pyrazolones proceeded
smoothly in short times and gave moderate to excellent yields. All of the results
are presented in Table 2.
123

F. Chen et al.
O
NH2
O
CN
N
N
CN
Et N
3
N
O
CN
EtOH, reflux
N
1
2
3
4
α-Methylenecarbonyl Compounds 2
O
O
O
O
N
Ph
O
N
N
N
N
H
N
O
O
a
b
c
d
e
O
n-Pr
Ph
Ph
N
O
O
N
O
N
N
N
N
N
Ph
N
H
H
Cl
f
g
h
i
Scheme 2 Synthesis of spiroindenoquinoxaline derivatives 4
Table 2 Synthesis of spiroindenoquinoxaline derivatives 4
a
b
Entry
Compound 2
Product 4
Time (h)
Yield (%)
M.p. (°C)
1
2
3
4
5
6
7
8
9
2a
2b
2c
2d
2e
2f
4a
4b
4c
4d
4e
4f
2
2
1
1
1
2
1
2
1
81
82
97
94
90
67
91
89
79
261–263
[300
259–261
2
7
228–230
217–218
236–238
230–232
272–274
236–238
2g
2h
2i
4g
4h
4i
Reaction conditions: indenoquinoxaline 1 (1 mmol), a-methylenecarbonyl compounds 2 (1 mmol),
malononitrile 3 (1 mmol), Et N (2 equiv.) as catalyst, in ethanol (10 ml), at reflux
3
a
Isolated yield
b
Literature references
On the basis of our previous knowledge and the results of our present study, we
propose a plausible mechanism for the construction of spiroindenoquinoxalines. As
shown in Scheme 3, firstly Knoevenagel condensation occurred with indenoqui-
noxaline 1 and malononitrile 3 to afford intermediate A. Then, a-methylenecarbonyl
compound 2 underwent subsequent Michael addition with intermediate A in the
presence of Et N to produce the intermediate B. Then, resulting B isomerized to C,
3
1
23

Synthesis of novel spiroindenoquinoxalines
O
CN
N+
H
N
Et
3
CN
N
1
NC
CN
CN
Et
3
N
H
O
NC
N
3
3
Et N
N
CN
CN
HO
N
N
2
H O
NEt
O H
3
NC
CN
N
O
2
N
3
Et N
A
O
H
NEt3
CN
O
CN
CN
O
NH
2
CN
CN
N
N
N
N
N
N
B
4
H
NEt
N
3
O
NH
O
N
H
NEt
3
O
C
CN
N
CN
N
CN
N
N
N
N
C
Scheme 3 Plausible mechanism for formation of 4
followed by an intramolecular ring-closure process to afford corresponding product
4
.
Inspired by these results, we attempted to choose 9-fluorenone, which has similar
structure to indenoquinoxaline, as substrate to extend the scope of this reaction. We
found that 9-fluorenone showed lower reactivity compared with indenoquinoxaline
1
(
, as lower yields were obtained and longer reaction times (24 h) were required
Scheme 4).
123

F. Chen et al.
R
O
O
NH2
CN
O
O
R
CN
Et N
3
R
O
CN EtOH, reflux, 24h
R
5
3
2
a, R=Me
6a 66%
6b 49%
2b, R=H
Scheme 4 Synthesis of spirofluorene derivatives 6
Experimental
Melting points were measured on an Electrothermal X6 microscopy digital melting
point apparatus. Elemental analyses were performed on a PerkinElmer EA2400II
elemental analyzer. Infrared (IR) spectra were recorded on a Bruker Equinox-55
1
13
spectrometer using KBr pellets. H and C nuclear magnetic resonance (NMR)
spectra were recorded in dimethyl sulfoxide (DMSO)-d on a Bruker AVANCE 300
6
and 75 MHz instrument with tetramethylsilane (TMS) at d = 0.00 ppm as internal
standard. Mass spectra were performed on an AB 4000 Q TRAP (USA).
Pyrazolones were prepared according to the method reported in the literature
[
30–32]. All other chemicals were of commercial grade without further purification.
General procedure for synthesis of spiroacenaphthylene derivatives (4a–i)
A mixture of compound 1 (1 mmol), a-methylenecarbonyl compound 2 (1 mmol),
malononitrile 3 (1 mmol), and Et N (2 equiv.) in 10 ml ethanol was stirred at reflux
3
till completion of the reaction as monitored by thin-layer chromatography (TLC);
the mixture was put into the fridge overnight. Then, the solid was filtered off and
washed with ethanol to obtain pure product (TLC pure). The isolated product was
further purified by recrystallization in ethanol or ethanol–acetone.
When compound 3d was used as substrate, the mixture was poured into water to
precipitate the product after completion of the reaction. The isolated product was
further purified by recrystallization in 60 % ethanol.
0
0 0 0 0 0 0 0
-Amino-7 ,7 -dimethyl-2,5 -dioxo-5 ,6 ,7 ,8 -tetrahydro-2H-spiro[(11H)-
2
indeno(1 ,2 -b)quinoxalin-11,4 -chromene]-3 -carbonitrile (4a)
0
0
0
0
1
White solid; m.p. 261–263 °C. H NMR (300 MHz, DMSO-d ): d 1.00 (3H, s, Me),
6
1
7
2
1
3
.03 (3H, s, Me), 2.03 (2H, q, J = 43.2 Hz, CH ), 2.68 (2H, q, J = 50.4 Hz, CH ),
1
.40 (2H, s, NH ), 7.53–8.19 (8H, m, ArH). C NMR (75 MHz, DMSO-d ): d 26.9,
7.6, 31.9, 47.1, 50.1, 58.5, 111.8, 117.6, 121.5, 128.8, 128.9, 129.1, 129.7, 132.3,
36.1, 140.9, 141.6, 151.9, 154.1, 158.9, 164.9, 165.5, 195.0. IR (KBr): 3,430,
2
2
3
2
6
-
1
,314, 3,176, 2,963, 2,200, 1,674, 1,601, 1,575, 1,352, 1,316, 1,220, 1,153 cm
?
MS, m/z (%): 443 (M , 100), 421 (95), 379 (15).
.
1
23

Synthesis of novel spiroindenoquinoxalines
0
0 0 0 0 0 0 0
-Amino-2,5 -dioxo-5 ,6 ,7 ,8 -tetrahydro-2H-spiro[(11H)-indeno(1 ,2 -
2
b)quinoxalin-11,4 -chromene]-3 -carbonitrile (4b)
0
0
1
White solid; m.p. [300 °C. H NMR (300 MHz, DMSO-d ): d 1.92 (2H, t,
6
J = 12.3 Hz, –CH CH –), 2.11 (2H, t, J = 7.8 Hz, –CH CH CH –), 2.77 (2H, t,
1
J = 5.4 Hz, –CH CH –), 7.36 (2H, s, NH ), 7.57–8.18 (8H, m, ArH). C NMR
2
2
2
2
2
3
2
2
2
(
75 MHz, DMSO-d ): d 19.7, 26.9, 36.5, 47.1, 58.5, 112.9, 117.6, 121.4, 124.6,
6
1
1
1
28.8, 128.9, 129.0, 129.6, 132.3, 136.0, 140.8, 141.6, 152.0, 154.1, 158.7, 165.6,
66.7, 195.1. IR (KBr): 3,378, 3,280, 3,243, 3,177, 2,195, 1,662, 1,602, 1,574,
-
1
,349, 1,331, 1,129, 1,072 cm . MS, m/z (%): 415 (M , 100), 393 (88). Anal.
?
Calcd. for C H N O : C, 73.46; H, 4.11; N, 14.28; Found: C, 73.32; H, 4.27; N,
2
4 16 4 2
1
4.08.
0
0
0
0
0
0
3
pyrano[2,3-c]pyrazole]-2 -carbonite (4c)
-Amino-7 -methyl-2-oxo-2H,5H -spiro[(11H)-indeno(1 ,2 -b)quinoxalin-11,1 -
0
1
Yellow solid; m.p. 259–261 °C. H NMR (300 MHz, DMSO-d ): d 1.14 (3H, s,
6
1
Me), 7.34 (2H, s, NH ), 7.48–8.21 (8H, m, ArH), 12.30 (1H, s, NH). C NMR
3
2
(
75 MHz, DMSO-d ): d 8.9, 18.5, 47.4, 56.0, 56.6, 96.3, 118.8, 121.6, 125.7, 128.9,
6
1
1
1
29.1, 129.6, 130.2, 133.0, 134.6, 135.5, 141.3, 142.0, 150.9, 152.8, 155.5, 162.5,
64.3. IR (KBr): 3,445, 3,112, 2,975, 2,190, 1,637, 1,607, 1,594, 1,488, 1,401,
-
1
?
,337 cm . MS, m/z (%): 401 (M , 55), 379 (100).
0
0 0 0 0 0
-Amino-5 -phenyl-7 -methyl-2-oxo-2H,5H -spiro[(11H)-indeno(1 ,2 -
3
b)quinoxalin-11,1 -pyrano[2,3-c]pyrazole]-2 -carbonite (4d)
0
0
1
Yellow solid; m.p. 228–230 °C (lit. [27] 236 °C). H NMR (300 MHz, DMSO-d ):
6
d 1.11 (3H, s, Me), 7.38–8.24 (10H, m, ArH and NH ). IR (KBr): 3,319, 3,290,
2
-
1
,141, 2,204, 1,658, 1,632, 1,598, 1,512, 1,397, 1,130 cm .
3
0
0 0 0 0 0
-Amino-5 -methyl-7 -methyl-2-oxo-2H,5H -spiro[(11H)-indeno(1 ,2 -
3
b)quinoxalin-11,1 -pyrano[2,3-c]pyrazole]-2 -carbonite (4e)
0
0
1
White solid; m.p. 215–218 °C. H NMR (300 MHz, DMSO-d ): d 1.01 (3H, s, Me),
6
1
3
3
.71 (3H, s, Me), 7.53–8.22 (10H, m, ArH and NH ). C NMR (75 MHz, DMSO-
2
d6): d 11.6, 33.7, 48.1, 57.6, 94.8, 118.3, 121.6, 125.8, 129.0, 129.1, 129.6, 130.3,
1
32.9, 135.6, 141.1, 141.3, 142.1, 145.4, 150.6, 152.9, 161.2, 163.9. IR (KBr):
-
,342, 3,292, 3,122, 2,199, 1,655, 1,629, 1,574, 1,561, 1,397, 1,130 cm . MS, m/
1
3
z (%): 415 (M , 100), 393 (58). Anal. Calcd. for C H N O: C, 70.40; H, 4.11; N,
?
2
3 16 6
2
1.42; Found: C, 70.42; H, 3.94; N, 21.41.
0
0
0
0
0
0
3
pyrano[2,3-c]pyrazole]-2 -carbonite (4f)
-Amino-7 -n-propyl-2-oxo-2H,5H -spiro[(11H)-indeno(1 ,2 -b)quinoxalin-11,1 -
0
1
Yellow solid; m.p. 236–239 °C. H NMR (300 MHz, DMSO-d ): d 0.12 (3H, t,
6
J = 14.7 Hz, –CH Me), 0.55 (2H, m, –CH CH Me), 1.44 (2H, t, J = 14.7 Hz,
2
2
2
123

F. Chen et al.
1
3
–
CH CH –), 7.33 (2H, s, NH ), 7.49–8.20 (8H, m, ArH), 12.30 (1H, s, NH).
2
C
2
2
NMR (75 MHz, DMSO-d ): d 12.8, 18.5, 20.7, 25.8, 47.6, 56.0, 56.6, 96.1, 100.2,
6
1
1
1
18.8, 121.6, 125.8, 128.9, 129.1, 129.5, 129.6, 130.3, 133.0, 135.5, 139.0, 141.3,
42.0, 151.4, 152.9, 155.3, 162.4, 164.7. IR (KBr): 3,307, 3,256, 3,173, 2,200,
-
,655, 1,606, 1,592, 1,489, 1,403 cm . MS, m/z (%): 429 (M , 100), 407 (65), 301
1
?
(
23). Anal. Calcd. for C H N O: C, 70.92; H, 4.46; N, 20.68; Found: C, 70.84; H,
24 18 6
4
.63; N, 20.83.
0
0 0 0 0 0
-Amino-5 -phenyl-7 -phenyl-2-oxo-2H,5H -spiro[(11H)-indeno(1 ,2 -
3
b)quinoxalin-11,1 -pyrano[2,3-c]pyrazole]-2 -carbonite (4g)
0
0
1
White solid; m.p. 230–232 °C. H NMR (300 MHz, DMSO-d ): d 7.42–8.14 (20H,
6
m, ArH and NH ). IR (KBr): 3,320, 3,141, 2,205, 1,658, 1,622, 1,600, 1,515, 1,455,
2
-
1
?
,397 cm . MS, m/z (%): 539 (M , 100), 517 (45), 301 (35). Anal. Calcd. for
1
C H N O: C, 76.73; H, 3.90; N, 16.27; Found: C, 76.18; H, 3.88; N, 15.81.
3
3 20 6
0
0 0 0 0 0
-Amino-7 -phenyl-2-oxo-2H,5H -spiro[(11H)-indeno(1 ,2 -b)quinoxalin-11,1 -
pyrano[2,3-c]pyrazole]-2-carbonite (4h)
3
1
Yellow solid; m.p. 272–274 °C. H NMR (300 MHz, DMSO-d ): d 7.39 (2H, s,
6
1
NH ), 6.26–8.13 (13H, m, ArH), 12.91 (1H, s, NH). C NMR (75 MHz, DMSO-
3
2
d6): d 47.6, 57.4, 96.9, 118.6, 121.5, 125.6, 127.0, 127.8, 128.1, 128.6, 128.8, 129.0,
1
IR (KBr): 3,340, 3,304, 3,240, 3,174, 2,197, 1,655, 1,604, 1,572, 1,498, 1,479,
29.5, 130.2, 132.8, 135.7, 138.9, 141.1, 141.9, 151.9, 153.1, 155.9, 161.9, 164.7.
-
1
?
1
C, 73.63; H, 3.66; N, 19.08; Found: C, 73.39; H, 3.81; N, 19.10.
,399 cm . MS, m/z (%): 463 (M , 68), 441 (100). Anal. Calcd. for C H N O:
27 16 6
0
0 0 0 0 0
-Amino-5 -(4-chlorophenyl)-7 -methyl-2-oxo-2H,5H -spiro[(11H)-indeno(1 ,2 -
3
b)quinoxalin-11,1 -pyrano[2,3-c]pyrazole]-2 -carbonite (4i)
0
0
1
Light-yellow solid; m.p. 236–238 °C. H NMR (300 MHz, DMSO-d ): d 1.01 (3H,
6
1
3
s, Me), 7.58–8.24 (14H, m, ArH and NH ). C NMR (75 MHz, DMSO-d ): d 11.8,
2
6
4
1
1
7.8, 57.6, 97.5, 118.0, 121.5, 121.7, 126.1, 129.0, 129.1, 129.4, 129.7, 129.9,
30.5, 130.6, 133.0, 135.7, 136.1, 141.3, 142.1, 144.2, 145.3, 150.2, 152.9, 161.0,
-
1
63.4. IR (KBr): 3,328, 3,292, 3,148, 2,201, 1,659, 1,592, 1,517, 1,487, 1,391 cm
?
.
MS, m/z (%): 489 (M , 25), 313 (30), 295 (48), 255 (100), 197 (90), 179 (95), 138
(85). Anal. Calcd. for C H ClN O: C, 68.78; H, 3.50; N, 17.19; Found: C, 68.88;
28 17 6
H, 3.61; N, 16.90.
General experimental procedure for synthesis of spirofluorene derivatives (6a, b)
A mixture of 9-fluorenone 5 (1 mmol), b-diketone 2a or 2b (1 mmol), malononitrile
3
(1 mmol), and Et N in 10.0 ml ethanol was stirred at reflux for 24 h. Upon
3
completion (monitored by TLC), the mixture was cooled to room temperature. Then
the solid was filtered off and washed with ethanol to obtain pure product (TLC
pure). The isolated product was further purified by recrystallization in ethanol.
1
23

Synthesis of novel spiroindenoquinoxalines
0
0 0 0 0 0 0 0
-Amino-7 ,7 -dimethyl-2,5 -dioxo-5 ,6 ,7 ,8 -tetrahydro-2H-spiro[(11H)-
2
indeno(1 ,2 -b)quinoxalin-11,4 -chromene]-3 -carbonitrile (6a)
0
0
0
0
1
White solid; m.p. 237–238 °C. H NMR (300 MHz, DMSO-d ): d 1.01 (6H, s,
6
2Me), 1.99 (2H, s, CH ), 2.62 (2H, s, CH ), 7.00 (2H, s, NH ), 7.24–7.80 (8H, m,
2 2 2
ArH). IR (KBr): 3,368, 3,323, 3,193, 2,958, 2,201, 1,676, 1,655, 1,603, 1,351,
-
1
,316 cm .
1
0
0 0 0 0 0 0 0
-Amino-2,5 -dioxo-5 ,6 ,7 ,8 -tetrahydro-2H-spiro[(11H)-indeno(1 ,2 -
2
b)quinoxalin-11,4 -chromene]-3 -carbonitrile (6b)
0
0
1
White solid; m.p. 258–259 °C. H NMR (300 MHz, DMSO-d ): d 1.91 (2H, q,
6
J = 18.6 Hz, –CH CH –), 2.08 (2H, q, J = 12.9 Hz, –CH CH CH –), 2.71 (2H, t,
J = 12.0 Hz, –CH CH –), 6.98 (2H, s, NH ), 7.21–7.80 (8H, m, ArH). IR (KBr):
2
2
2
2
2
2
2
2
-
,473, 3,371, 2,197, 1,670, 1,580, 1,347, 1,324, 1,304 cm .
1
3
Conclusion
A simple and efficient synthesis of some novel spiroindenoquinoxalines was
achieved via a one-pot reaction involving indenoquinoxaline, various b-diketones/
pyrazolones, and malononitrile.
Acknowledgments The authors are grateful to the National Natural Science Foundation of China (nos.
21372099, 21072077) and the Guangdong Natural Science Foundation (no. 10151063201000051) for
financial support.
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