A. Olyaei et al.
9,11-Diamino-6-hydroxy-12-(3-bromophenyl)-12H-benzo[5,6]chromeno[2,3-
b]pyridine-10-carbonitrile (9c)
Cream solid; mp [ 300 °C; IR (KBr, cm-1): 3494, 3355, 3239, 3062, 2900, 2202,
1623, 1605, 1469, 1400, 1322, 1253, 1079; H NMR (300 MHz, DMSO-d6): 6.04
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(s, 1H, methine-H), 6.52 (s, 2H, NH2), 6.88 (s, 2H, NH2), 7.17–7.41 (m, 6H, Ar–H),
7.68 (s, 1H, Ar–H), 8.12 (d, 1H, J = 8.4 Hz, Ar–H), 10.25 (s, 1H, OH); 13C NMR
(75 MHz, DMSO-d6): 71.44, 91.56, 109.96, 116.46, 116.94, 119.36, 122.04, 123.31,
124.19, 125.02, 125.46, 126.82, 127.07, 129.83, 130.24, 131.18, 131.54, 140.88,
146.11, 147.83, 157.06, 159.39, 160.10; MS m/z (%): 460 (M ? 2), 458 (M?), 405,
391, 330, 303, 275, 237, 189, 164, 139 (100), 119, 111, 105, 91, 77; Anal. calcd. for
C23H15BrN4O2: C, 60.13; H, 3.26; N, 12.20. Found: C, 60.11; H, 3.30; N, 12.27.
9,11-Diamino-6-hydroxy-12-(4-bromophenyl)-12H-benzo[5,6]chromeno[2,3-
b]pyridine-10-carbonitrile (9d)
Yellow solid; mp [ 300 °C; IR (KBr, cm-1): 3498, 3351, 3239, 3077, 2969, 2202,
1623, 1565, 1473, 1400, 1322, 1257, 1149; H NMR (300 MHz, DMSO-d6): 6.04
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(s, 1H, methine-H), 6.50 (s, 2H, NH2), 6.86 (s, 2H, NH2), 7.19–7.41 (m, 7H, Ar–H),
7.66–8.13 (m, 2H, Ar–H), 10.24 (s, 1H, OH); 13C NMR (75 MHz, DMSO-d6):
71.42, 91.69, 110.28, 117.00, 119.49, 120.01, 123.42, 124.07, 125.07, 125.39,
125.98, 127.01, 129.94, 131.71, 140.80, 144.60, 146.13, 147.31, 157.09, 159.34,
160.05; MS m/z (%): 460 (M ? 2)?, 458 (M?), 405, 391, 330, 303, 275, 237, 219,
191, 160, 139, 119, 111, 105 (100), 91, 77, 57, 43; Anal. calcd. for C23H15BrN4O2:
C, 60.13; H, 3.26; N, 12.20. Found: C, 60.11; H, 3.25; N, 12.28.
9,11-Diamino-6-hydroxy-12-(4-flourophenyl)-12H-benzo[5,6]chromeno[2,3-
b]pyridine-10-carbonitrile (9e)
Green solid; mp [ 300 °C; IR (KBr, cm-1): 3498, 3351, 3243, 3077, 2923, 2202,
1623, 1566, 1511, 1469, 1403, 1257; H NMR (300 MHz, DMSO-d6): 6.04 (s, 1H,
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methine-H), 6.48 (s, 2H, NH2), 6.85 (s, 2H, NH2), 6.99–7.67 (m, 7H, Ar–H),
7.98–8.16 (m, 2H, Ar–H), 10.21 (s, 1H, OH); 13C NMR (75 MHz, DMSO-d6):
71.41, 92.08, 110.16, 115.39, 115.66, 115.97, 116.26, 119.92, 123.50, 124.01,
125.08, 126.98, 129.49, 129.59, 131.54, 132.64, 140.77, 146.14, 157.04, 159.39;
MS m/z (%): 398 (M?), 391, 330, 303, 275, 237, 191, 164, 151, 141, 139 (100), 119,
111, 105, 91, 77, 57, 43; Anal. calcd. for C23H15FN4O2: C, 69.34; H, 3.76; N, 14.07.
Found: C, 69.30; H, 3.71; N, 14.11.
9,11-Diamino-6-hydroxy-12-(3-nitrophenyl)-12H-benzo[5,6]chromeno[2,3-
b]pyridine-10-carbonitrile (9f)
White solid; mp [ 300 °C; IR (KBr, cm-1): 3490, 3359, 3243, 3081, 2927, 2206,
1623, 1565, 1523, 1469, 1400, 1346, 1263, 1203; 1H NMR (300 MHz, DMSO-d6):
6.22 (s, 1H, methine-H), 6.56 (s, 2H, NH2), 6.96 (s, 2H, NH2), 7.22 (s, 7H, Ar–H),
7.32–8.15 (m, 7H, Ar–H), 8.43 (s, 1H, Ar–H), 10.31 (s, 1H, OH); 13C NMR
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