G Model
CCLET 3833 1–7
6
A. Yazdani-Elah-Abadi et al. / Chinese Chemical Letters xxx (2016) xxx–xxx
2
2
2
2
2
2
2
2
2
2
2
2
2
2
2
2
2
2
2
80
81
82
83
84
85
86
87
88
89
90
91
92
93
94
95
96
97
98
1
1
36.3, 137.8, 139.3, 139.5, 140.3, 147.9, 151.0, 152.9, 153.4, 158.3,
59.4, 167.6; Anal. Calcd. for C33 O: C, 75.1; H, 3.2; N, 18.5%.
Found: C, 75.3; H, 3.3; N, 18.5%. MS (m/z, %): 527 (M , 1), 471 (36),
68 (38), 252 (58), 105 (90), 57 (100).
-Amino-1-(4-cyanophenyl)-1H-benzo[a]pyrano[2,3-c]phena-
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3
3
33
34
17 7
H N
+
2
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335
3
pyrazine and quinoxaline derivatives, J. Med. Chem. 45 (2002) 5604–5606.
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3
3
337
36
antimicrobial activity of novel quinoxaline derivatives, J. Chin. Chem. Soc.
zine-2-carbonitrile (10a): brown solid; yield 91% (under
and 93% (under MW, 0.395 g), mp > 330 C; IR (KBr, cm ):
D
, 0.387 g)
5
4 (2007) 469–478.
0
[22] G. Aguirre, H. Cerecetto, R. Di Maio, et al., Quinoxaline N,N -dioxide
ꢀ
ꢂ1
n
max
3
3
38
39
derivatives and related compounds as growth inhibitors of Trypanosoma
cruzi. Structure–activity relationships, Bioorg. Med. Chem. Lett. 14 (2004)
3350, 3310, 3185, 2420, 2225, 1658, 1624, 1591, 1548, 1464, 1397,
1
1
375, 1345, 1292, 1239, 1178, 1115, 1078, 1048, 943, 845, 762;
NMR (400 MHz, DMSO-d ): 5.57 (s,1H, CH), 7.51 (s, 2H, NH ), 7.61
d, 2H, J = 8.4 Hz, Ar-H), 7.70 (d, 2H, J = 8.4 Hz, Ar-H), 7.92-7.95 (m,
H
340
3
835–3839.
6
d
2
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341
(
3
3
42
43
2H, Ar-H), 7.96–7.98 (m, 1H, Ar-H), 7.99–8.03 (m, 1H, Ar-H), 8.11–
2
254.
8.13 (m, 1H, Ar-H), 8.26–8.29 (m, 1H, Ar-H), 8.45 (d, 1H, J = 7.6 Hz,
[
24] S.T. Hazeldine, L. Polin, J. Kushner, et al., Synthesis and biological evaluation of
some bioisosteres and congeners of the antitumor agent, 2-(4-[(7-chloro-2-
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13
344
3
3
6
Ar-H), 9.24 (d,1H, J = 7.2 Hz, Ar-H); C NMR (100 MHz, DMSO-d ): d
45
46
3
1
1
1
8.2, 57.3, 109.8, 112.9, 119.1, 120.3, 122.7, 125.3, 125.9, 129.1, 129.2,
29.5, 129.8, 130.6, 130.8, 131.0, 131.3, 132.8, 140.5, 140.9, 141.9,
46.9, 151.2, 160.2; Anal. Calcd. for C27 O: C, 76.2; H, 3.5; N,
6.4%. Found: C, 76.2; H, 3.5; N, 16.3%. MS (m/z, %): 425 (M , 1), 323
3), 180 (22), 121 (30), 101 (43), 86 (100).
3130–3137.
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Top. Curr. Chem. 189 (1997) 1–120.
347
15 5
H N
+
[26] G.P. Ellis, in: A. Weissberger, E.C. Taylor (Eds.), The Chemistry of Heterocyclic
Compounds Chromenes, Chromanes and Chromones, John Wiley, New York,
NY, 1977, pp. 11–139 (Chapter II).
3
349
48
(
[
27] E.A. Hafez, M.H. Elnagdi, A.G.A. Elagemey, F.M.A.A. El-Taweel, Nitriles in
heterocyclic synthesis: novel synthesis of benzo[c]coumarin and of benzo[c]
pyrano[3,2-c]quinoline derivatives, Heterocycles 26 (1987) 903–907.
3
3
50
51
2
99
Acknowledgments
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28] T. Narender, Shweta, S. Gupta, A convenient and biogenetic type synthesis of
few naturally occurring chromeno dihydrochalcones and their in vitro anti
leishmanial activity, Bioorg. Med. Chem. Lett. 14 (2004) 3913–3916.
3
3
3
00 Q2
01
352
353
We gratefully acknowledge financial support from the Research
Council of the University of Sistan and Baluchestan and Islamic
Azad University of Yazd.
02
[29] K. Asres, A. Seyoum, C. Veeresham, F. Bucar, S. Gibbons, Naturally derived anti-
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356
55
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Please cite this article in press as: A. Yazdani-Elah-Abadi, et al., Theophylline as a new and green catalyst for the one-pot synthesis of spiro