ORGANIC PREPARATIONS AND PROCEDURES INTERNATIONAL
7
ꢁ
1 1
;
stretching) cm
HNMR (400 MHz, DMSO-d ) d (ppm): 5.53 (s, 1H), 7.04-7.08 (m,
6
1
7
H), 7.12-7.16 (m, 2H), 7.43-7.53 (m, 2H), 7.62 (d, J ¼ 8.2 Hz, 2H), 7.67-7.70 (m, 1H),
.72 (d, J ¼ 8.2 Hz, 2H) ppm.
Anal. Calcd. for C H N O : C, 69.96; H, 3.82; N, 12.24. Found: C, 69.94; H, 3.83;
2
0
13 3 3
N, 12.21.
2
-Amino-4-(3-hydroxyphenyl)-4H-benzo[h]chromene-3-carbonitrile (6f)
ꢀ
ꢁ1
mp 231-232 C; FT-IR (KBr, cm ) ꢀ
1
3420 (NH stretching), 3300 (O-H stretching),
2
max
ꢁ
1 1
650, 1580 (aromatic C¼C stretching), 2200 (CN stretching) cm ; HNMR (400 MHz,
DMSO-d ) d (ppm): 4.79 (s, 1H), 6.60-6.62 (m, 2H), 6.70 (d, J ¼ 7.6 Hz, 1H), 7.09-7.14
6
(
m, 2H), 7.15 (s, 2H, NH ), 7.56-7.66 (m, 3H), 7.89 (d, J ¼ 8.0 Hz, 1H), 8.22 (d,
2
J ¼ 8.4 Hz, 1H), 9.37 (s, 1H, OH) ppm.
Anal. Calcd. for C H N O : C, 76.42; H, 4.49; N, 8.91. Found: C, 76.46; H, 4.46; N,
2
0
14 2 2
8. 95.
2
-Amino-4-(2-methoxyphenyl)-4H-benzo[h]chromene-3-carbonitrile (6g)
ꢀ
ꢁ1
m.p. 212-214 C; FT-IR (KBr, cm ) ꢀ
1
3
3470 (NH stretching), 2170 (CN stretching),
2
max
ꢁ
1 1
660, 1600 (aromatic C¼C stretching) cm ; HNMR (400 MHz, DMSO-d ) d (ppm):
6
.81 (s, 3H), 5.26 (s, 1H), 6.88 (t, J ¼ 6.8 Hz, 1H), 7.04 (t, J ¼ 7.2 Hz, 2H), 7.10 (s, 2H,
NH ), 7.13 (d, J ¼ 8.14, 1H), 7.21 (t, J ¼ 7.2 Hz, 1H), 7.56 (t, J ¼ 7.6 Hz, 2H), 7.63 (t,
2
J ¼ 6.8 Hz, 1H), 7.86 (d, J ¼ 8.0Hz, 1H), 8.22 (d, J ¼ 8.0 Hz, 1H) ppm.
Anal. Calcd. for C H N O : C, 76.81; H, 4.91; N, 8.53. Found: C, 76.87; H, 4.93; N,
2
1
16 2 2
8. 56.
2
,2’-(Butane-1,4-diyl)bis(2-amino-4-(2-methoxyphenyl)-4H-benzo[h]chromene-3-
carbonitrile) (6h)
ꢀ
ꢁ1
m.p. 280-281 C; FT-IR (KBr, cm ) ꢀ
1
1
3467 (NH stretching), 2192 (CN stretching),
2
max
ꢁ
1 1
662, 1596 (aromatic C¼C stretching) cm ; HNMR (400 MHz, DMSO-d ) d (ppm):
6
.47-1.58 (m, 4H), 3.66-3.90 (m, 4H), 5.10 (s, 2H), 6.88-6.92 (m, 4H), 6.99-7.05 (s, 2H,
NH ), 7.03-7.06 (m, 2H), 7.15-7.21 (m, 4H), 7.49-7.59 (m, 6H), 7.81 (d, J ¼ 8.0 Hz, 2H),
2
1
3
8
1
1
.19 (d, J ¼ 8.4 Hz, 2H) ppm; C NMR (100 MHz, DMSO-d ) d (ppm): 160.9, 156.6,
6
43.3, 133.2, 133.0, 129.9, 128.9, 128.0, 126.9 (2C), 126.2, 124.0, 123.1, 121.1, 121.0 (2C),
20.8, 118.2, 112.6, 67.7, 55.5, 26.0 ppm.
Anal. Calcd. for C H N O : C, 77.40; H, 5.02; N, 8.21. Found: C, 77.43; H, 5.00; N,
4
4
34 4 4
8. 21.
2
,2’-(Pentane-1,5-diyl)bis(2-amino-4-(2-methoxyphenyl)-4H-benzo[h]chromene-3-
carbonitrile) (6i)
ꢀ
ꢁ1
m.p. 298-299 C; FT-IR (KBr, cm ) ꢀ
1
1
3460 (NH stretching), 2200 (CN stretching),
2
max
ꢁ
1 1
650, 1550 (aromatic C¼C stretching) cm ; H NMR (400 MHz, DMSO-d ) d (ppm):
6
.19-1.58 (m, 6H), 3.60 (t, J ¼ 3.8Hz, 4H), 5.11 (s, 2H), 6.87-6.90 (m, 3H), 7.01-7.05