A. M. El-Agrody et al. · Benzo[f]chromenes
585
by D O). Ð 10b: IR (film): ν = 3363 (NH), 3000, (C=N). Ð 1H NMR (300.069 MHz, DMSO-d6): δ =
˜
2939,22820 (stretching CH), 1643 cmÐ1 (C=N). Ð 3.63 (s, 3H, OMe), 3.89 (s, 3H, 2-OMe), 5.70 (s,
1H NMR (300.069 MHz, DMSO-d6): δ = 3.34 (s, 1H, 1-H), 6.02 (br, 2H, NH2 exchanged by D2O),
3H, 10-NÐMe), 3.63 (s, 3H, OMe), 3.92 (s, 3H, 7.44 (br, 1H, NH exchanged by D2O), 6.76Ð7.81
2-OMe), 5.79 (s, 1H, 1-H), 7.34 (br, 1H, NH ex- (m, 9H, ArÐH), 8.09 ppm (s, 1H, 9-H). Ð 13C
changed by D2O), 6.77Ð7.81 (m, 9H, ArÐH), NMR (75.461 MHz, DMSO-d6): δ = 35.33 (C-12),
8.10 ppm (s, 1H, 9-H). Ð 10c: IR (film): ν = 3400, 54.89 (OMe), 55.30 (OMe), 99.65 (C-11a), 103.12
˜
3320 (NH2), 3317 (NH), 3275 (OH), 3067, 2984, (C-1), 113.55 (C-1b), 114.69 (aromatic), 115.92
2910, 2833 (stretching CH), 1647 cmÐ1 (C=N). Ð (C-3), 116.64 (C-6), 118.73 (C-4a), 118.75 (C-5),
1H NMR (300.069 MHz, DMSO-d6): δ = 3.62 (s, 126.05 (C-4), 128.73 (aromatic), 129.40 (C-1a),
3H, OMe), 5.59 (s, 1H, 1-H), 5.66 (br, 2H, NH2), 130.05 (C-6a), 131.92 (aromatic), 135.93 (C-2),
6.73Ð7.74 (m, 9H, ArÐH), 8.02 (s, 1H, 9-H), 9.82 147.75 (C-7a), 155.08(aromatic), 157.08 (C-9),
(br, 1H, NH), 10.50 (s, 1H, 2-OH). Ð 13C NMR 158.02 (C-11). Ð 11a: IR (film): ν = 3348(OH),
˜
(75.461 MHz, DMSO-d6): δ = 36.02 (C-12), 55.66 2950, 2918, 2887, 2841, 2808 (stretching CH), 2185
1
(OMe), 100.64 (C-11a), 106.45 (C-1), 110.00 cmÐ1 (CN). Ð H NMR (300.069 MHz, DMSO-
(C-1b), 114.21 (C-3), 114.48(aromatic), 115.18
d6): δ = 2.99 (s, 3H, NÐMe), 3.15 (s, 3H, NÐMe),
(C-6), 117.56 (C-4a), 126.04 (C-5), 128.00 (C-4), 3.69 (s, 3H, OMe), 5.07 (s, 1H, 1-H), 6.82Ð7.80 (m,
129.47 (aromatic), 129.96 (C-1a), 130.06 (C-6a), 9H,ArÐH), 8.44 (s, 1H, N=CH), 9.81 ppm (s, 1H,
133.06 (aromatic), 136.63 (C-2), 148.52 (C-7a), 9-OH). Ð 11b: IR (film): ν = 3030, 3000, 2939, 2800
˜
155.80 (aromatic), 157.00 (C-9), 158.47 (C-11). Ð (stretching CH), 2191 cmÐ1 (CN). Ð 1H NMR
MS (EI, 70 eV): m/z (%) = 386 (14) [M+], 265 (300.069 MHz, DMSO-d6): δ = 3.01 (s, 3H,
(100) [M+ÐC6H3 ·OMe and NH], 238(2)8
NÐMe), 3.16 (s, 3H, NÐMe), 3.68(s, 3H, OMe),
[M+ÐHCN], 184 (5) [M+Ð2HCN]. Ð 10d: IR 3.76 (s, 3H, 9-OMe), 5.35 (s, 1H, 1-H), 6.82Ð7.85
(film): ν = 3364, 3283 (NH ), 3200 (NH), 3005, (m, 9H, ArÐH), 8.47 ppm (s, 1H, N=CH).
˜
2
2934, 2934, 2908, 2833 (stretching CH), 1655 cmÐ1
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