6
ABDOLMOHAMMADI AND DAHI-AZAR
1
52.8, 153.1, 153.9, 155.2, 157.3, 161.0, 169.5, 171.3 ppm.
CH), 7.44 (m, 3 H, H-Ar), 7.58 (d, 1 H, J = 6.6 Hz, H-Ar),
7.60 (t, 1 H, J = 7.8 Hz, H-Ar), 7.65 (m, 2 H, H-Ar), 7.71
(t, 1 H, J = 6.8 Hz, H-Ar), 7.79 (t, 1 H, J = 7.3 Hz, H-Ar),
Anal. calc. For C H N O (514.49): C 72.37, H 3.53, N
31
18 2 6
5
.44; found: C 72.55, H 3.65, N 5.29.
7.83 (d, 1 H, J = 7.5 Hz, H-Ar), 7.90 (s, 1 H, H-Ar), 8.10
(
m, 3 H, H-Ar), 8.32 (d, 1 H, J = 6.7 Hz, H-Ar), 13.12
13
3
.3.2 | 11-Bromo-7-(4-hydroxy-2-oxo-2H-[1]
(brs, 1 H, OH) ppm. C-NMR: δ = 20.6, 41.8, 89.5, 110.1,
114.9, 116.4, 116.8, 117.3, 119.5, 120.2, 120.9, 121.4, 124.8,
125.0, 125.8, 128.4, 128.8, 129.6, 130.2, 132.1, 142.4, 150.6,
151.0, 153.7, 156.3, 154.6, 155.7, 160.4, 169.5, 171.9 ppm.
Anal. calc. For C H N O (528.52): C 72.72, H 3.81, N
benzopyran-3-yl)-9-[(E)-2-phenyl-1-diazenyl]-
6
6
H,7H-[1]benzopyrano[4,3-b][1]benzopyran-
-one (5b)
32
20 2 6
ꢁ
Yellow solid, yield: 0.546 g (92%), m.p. 285–287 C. IR
5.30; found: C 72.85, H 4.01, N 5.41.
ꢂ1
(KBr) (νmax/cm ): 3260, 1707, 1663, 1629, 1555, 1476,
1
1
329, 1210. H-NMR: δ = 5.70 (s, 1 H, CH), 7.12 (t, 1 H,
J = 7.8 Hz, H-Ar), 7.25 (m, 3 H, H-Ar), 7.49 (m, 2 H, H-
Ar), 7.52 (m, 3 H, H-Ar), 7.60 (t, 2 H, J = 7.9 Hz, H-Ar),
3.3.5 | 11-Bromo-7-(4-hydroxy-2-oxo-2H-[1]
benzopyran-3-yl)-9-[(E)-2-(4-methylphenyl)-
1-diazenyl]-6H,7H-[1]benzopyrano[4,3-b][1]
benzopyran-6-one (5e)
7
.99 (d, 2 H, J = 8.0 Hz, H-Ar), 8.19 (d, 2 H, J = 8.1 Hz,
13
H-Ar), 13.33 (brs, 1 H, OH) ppm. C-NMR: δ = 40.3,
9
1
1
1
6
1.2, 109.8, 115.0, 116.5, 117.0, 117.6, 118.4, 120.1, 122.6,
24.4, 125.0, 126.0, 126.4, 129.0, 129.7, 131.3, 132.5, 132.9,
34.8, 150.3, 153.0, 153.4, 153.8, 156.1, 158.5, 162.8, 169.9,
70.8 ppm. Anal. calc. For C H BrN O (593.39): C
ꢁ
Yellow solid, yield: 0.571 g (94%), m.p. 289–291 C. IR
ꢂ1
(KBr) (νmax/cm ): 3240, 1701, 1635, 1569, 1520, 1499,
1336, 1210. H-NMR: δ = 2.18 (s, 3 H, CH ), 5.80 (s, 1 H,
CH), 7.19 (d, 2 H, J = 7.8 Hz, H-Ar), 7.30 (d, 1 H,
J = 8.1 Hz, H-Ar), 7.39 (t, 1 H, J = 7.2 Hz, H-Ar), 7.52
1
31
17
2
6
3
2.75, H 2.89, N 4.72; found: C 62.64, H 2.73, N 4.53.
(
m, 2 H, H-Ar), 7.60 (m, 2 H, H-Ar), 7.72 (t, 1 H,
3
.3.3 | 7-(4-Hydroxy-2-oxo-2H-[1]
benzopyran-3-yl)-11-methoxy-9-[(E)-2-phenyl-
-diazenyl]-6H,7H-[1]benzopyrano[4,3-b][1]
benzopyran-6-one (5c)
J = 7.2 Hz, H-Ar), 7.81 (d, 2 H, J = 7.8 Hz, H-Ar), 8.14
13
(m, 3 H, H-Ar), 12.30 (brs, 1 H, OH) ppm. C-NMR:
δ = 21.7, 42.6, 92.4, 108.7, 115.1, 116.5, 117.0, 117.4,
118.1, 119.4, 122.9, 125.8, 126.4, 127.1, 127.9, 129.3, 130.0,
1
130.6, 130.8, 132.7, 143.0, 150.3, 151.9, 153.7, 154.4, 157.1,
ꢁ
Yellow solid, yield: 0.506 g (93%), m.p. 240–242 C. IR
159.4, 163.6, 170.2, 170.6 ppm. Anal. calc. For
C H BrN O (607.41): C 63.28, H 3.15, N 4.61; found: C
ꢂ1
(KBr) (νmax/cm ): 3316, 1708, 1660, 1643, 1575, 1465,
32
19
2 6
1
1
1
359, 1218. H-NMR: δ = 3.69 (s, 3 H, OCH ), 5.68 (s,
63.43, H 3.32, N 4.82.
3
H, CH), 7.08 (s, 1 H, H-Ar), 7.34 (d, 1 H, J = 7.6 Hz, H-
Ar), 7.38 (d, 1 H, J = 7.9 Hz, H-Ar), 7.48 (d, 2 H,
J = 8.2 Hz, H-Ar), 7.53 (m, 3 H, H-Ar), 7.65 (d, 2 H,
J = 7.9 Hz, H-Ar), 8.04 (d, 2 H, J = 7.9 Hz, H-Ar), 8.12
3.3.6 | 7-(4-Hydroxy-2-oxo-2H-[1]
benzopyran-3-yl)-11-methoxy-9-[(E)-
2-(4-methylphenyl)-1-diazenyl]-6H,7H-[1]
benzopyrano[4,3-b][1]benzopyran-6-one (5f)
13
(m, 3 H, H-Ar), 12.29 (brs, 1 H, OH) ppm. C-NMR:
δ = 40.8, 56.7, 92.1, 111.2, 114.1, 115.3, 116.6, 117.6,
1
1
1
17.8, 118.2, 122.5, 122.9, 124.1, 124.5, 124.8, 129.6, 130.0,
31.5, 131.8, 133.6, 149.1, 149.4, 152.1, 153.7, 155.4, 156.5,
57.6, 159.9, 168.8, 172.2 ppm. Anal. calc. For
ꢁ
Yellow solid, yield: 0.519 g (93%), m.p. 252–253 C. IR
ꢂ1
(KBr) (νmax/cm ): 3257, 1711, 1665, 1633, 1570, 1453,
1391, 1205. H-NMR: δ = 2.23 (s, 3 H, CH ), 3.92 (s, 3 H,
1
C H N O (544.52): C 70.58, H 3.70, N 5.14; found: C
32
20
2
7
3
7
0.46, H 3.84, N 5.04.
OCH ), 5.69 (s, 1 H, CH), 6.99 (s, 1 H, H-Ar), 7.08 (d, 1 H,
3
J = 8.1 Hz, H-Ar), 7.19 (t, 1 H, J = 8.3 Hz, H-Ar), 7.38
(
m, 4 H, H-Ar), 7.45 (m, 2 H, H-Ar), 7.56 (t, 1 H,
3
.3.4 | 7-(4-Hydroxy-2-oxo-2H-[1]
benzopyran-3-yl)-9-[(E)-2-(4-methylphenyl)-
-diazenyl]-6H,7H-[1]benzopyrano[4,3-b][1]
benzopyran-6-one (5d)
J = 7.3 Hz, H-Ar), 7.66 (d, 1 H, J = 7.3 Hz, H-Ar), 8.07
13
(m, 3 H, H-Ar), 12.35 (brs, 1 H, OH) ppm. C-NMR:
δ = 20.9, 42.4, 55.9, 91.8, 112.4, 115.5, 115.6, 118.3, 119.1,
119.6, 120.1, 121.0, 124.5, 124.9, 125.1, 125.6, 130.5, 131.8,
1
132.3, 134.0, 142.6, 150.1, 151.9, 153.0, 153.7, 154.1, 156.2,
ꢁ
Yellow solid, yield: 0.481 g (91%), m.p. 228–230 C. IR
157.9, 160.0, 172.7, 173.5 ppm. Anal. calc. For
C H N O (558.54): C 70.96, H 3.97, N 5.01; found: C
ꢂ1
(KBr) (νmax/cm ): 3290, 1716, 1659, 1628, 1589, 1473,
33
22 2 7
1
1
377, 1209. H-NMR: δ = 2.21 (s, 3 H, CH ), 5.65 (s, 1 H,
70.84, H 4.13, N 5.20.
3