Med Chem Res
δ: 9.58–7.26 (m, 8H, aromatic), 7.38 (bs, 2H, NH2), 5.46 (s,
1H, H-4); 13C NMR (125 MHz, DMSO-d6) δ: 160.32 (C-2),
151.22 (C-9), 143.02 (C-10b), 137.95 (C-10a), 132.48 (C-
7), 129.31 (C-5), 125.37 (C-6), 124.95 (C-6a), 123.51 (C-
8), 119.83 (C-4a), 119.65 (CN), 53.62 (C-3), 38.89 (C-4),
142.94, 132.34, 132.00, 131.19, 131.04, 125.57 (aromatic);
MS m/z (%): 405 (M++4, 2.22), 403 (M++2, 12.26), 401
(M+, 18.11) with a base peak at 256 (100); anal. calcd. for
C19H10Cl3N3O: C, 56.67; H, 2.50; N, 10.44. Found: C,
56.70; H, 2.63; N, 10.54 %.
(C-9), 144.95 (C-10b), 137.47 (C-10a), 135.98 (C-7),
127.77 (C-5), 126.67 (C-6), 123.68 (C-6a), 122.20 (C-8),
121.30 (C-4a), 117.68 (CN), 55.59 (C-3), 40.50 (C-4),
143.03, 131.63, 129.94, 127.45, 121.78 (aromatic), MS m/z
(%): 380 (M+–Cl+4, 2.08), 378 (M+–Cl+2, 5.02), 376
(M+–Cl, 3.37) with a base peak at 222 (100); anal. calcd. for
C19H11BrClN3O: C, 55.30; H, 2.69; N, 10.18. Found: C,
55.37; H, 2.73; N, 10.23 %.
2-amino-6-chloro-4-(3,5-dibromo-2-methoxyphenyl)-
4H-pyrano[3,2-h]quinoline-3-carbonitrile (5j)
2-amino-6-chloro-4-(2,6-dichlorophenyl)-4H-pyrano
[3,2-h]quinoline-3-carbonitrile (5g)
Pale yellow Crystals from ethanol; yield 81 %; m.p. 223-
225 °C; IR (KBr, υmax cm−1): 3432, 3337, 3182 (NH2),
1
Colorless needles from benzene; yield 82 %; m.p. > 300 °C;
IR (KBr, υmax cm−1): 3475, 3325, 3188 (NH2), 2199 (CN),
2192 (CN), 1657 (C=N); H NMR (500 MHz, DMSO-d6)
δ: 9.07–7.29 (m, 7H, aromatic), 7.39 (bs, 2H, NH2), 5.25 (s,
1H, H-4), 3.69 (s, 3H, OCH3); 13C NMR (125 MHz,
DMSO-d6) δ: 160.43 (C-2), 151.21 (C-9), 142.78 (C-10b),
138.06 (C-10a), 134.91 (C-7), 132.30 (C-5), 125.25 (C-6a),
124.90 (C-4a), 123.43 (C-8), 120.93 (C-6), 117.00 (CN),
61.32 (CH3), 54.19 (C-3), 36.78 (C-4), 154.34, 141.49,
132.50, 125.86, 120.00, 118.29 (aromatic); MS m/z (%):
490 (M+–Cl+6, 0.85), 488 (M+–Cl+4, 3.53), 486 (M+–Cl
+2, 4.41), 484 (M+–Cl, 2.19) with a base peak at 222 (100);
anal. calcd. for C20H12Br2 ClN3O2: C, 46.05; H, 2.32; 6.80;
N, 8.06. Found: C, 46.16; H, 2.41; N, 8.13 %.
1
1661 (C=N); H NMR (500 MHz, DMSO-d6) δ: 9.07–7.05
(m, 8H, aromatic), 7.42 (bs, 2H, NH2), 6.03 (s, 1H, H-4);
13C NMR (125 MHz, DMSO-d6) δ: 160.59 (C-2), 151.30
(C-9), 143.55 (C-10b), 137.71 (C-10a), 132.53 (C-7),
130.37 (C-5), 125.37 (C-6), 124.73 (C-6a), 123.49 (C-8),
119.38 (C-4a), 118.91 (CN), 51.95 (C-3), 37.04 (C-4),
136.56, 135.54, 134.96, 130.90, 128.85, 124.86 (aromatic);
MS m/z (%): 405 (M++4, 2.06), 403 (M++2, 11.77), 401
(M+, 18.14) with a base peak at 256 (100); anal. calcd. for
C19H10Cl3N3O: C, 56.67; H, 2.50; N, 10.44. Found: C,
56.80; H, 2.63; N, 10.60 %.
2-amino-4-(2-chlorophenyl)-9-methyl-4H-pyrano[3,2-h]
2-amino-6-chloro-4-(3,4-dichlorophenyl)-4H-pyrano
[3,2-h]quinoline-3-carbonitrile (5h)
quinoline-3-carbonitrile (7a)
Yellow crystals from ethanol; yield 88 %; m.p. 238–239 °C;
IR (KBr, υmax cm−1): 3470, 3366, 3196 (NH2), 2195 (CN),
1659 (C=N); H NMR (500 MHz, DMSO-d6) δ: 8.46–6.82
Pale yellow needles from benzene; yield 82 %; m.p.
1
257–259 °C; IR (KBr, υmax cm−1): 3470, 3321, 3199 (NH2),
1
2199 (CN), 1658 (C=N); H NMR (500 MHz, DMSO-d6)
(m, 8H, aromatic), 7.16 (bs, 2H, NH2), 5.43 (s, 1H, H-4),
2.72 (s, 3H, CH3); 13C NMR (125 MHz, DMSO-d6) δ:
160.54 (C-2), 159.11 (C-9), 142.86 (C-10b), 136.91 (C-
10a), 136.30 (C-7), 128.90 (C-5), 125.21 (C-6a), 123.84 (C-
8), 122.93 (C-4a), 120.52 (C-6), 120.07 (CN), 54.73 (C-3),
38.56 (C-4), 24.84 (CH3) 142.16, 136.08, 131.97, 130.42,
129.84, 126.20 (aromatic), MS m/z (%): 349 (M++2, 1.56),
347 (M+,4.63) with a base peak at 236 (100); anal. calcd. for
C20H14ClN3O: C, 69.07; H, 4.06; N, 12.08. Found: C,
69.11; H, 4.14; N, 12.13 %.
δ: 9.04–7.27 (m, 8H, aromatic), 7.39 (bs, 2H, NH2), 5.06 (s,
1H, H-4); 13C NMR (125 MHz, DMSO-d6) δ: 160.18 (C-2),
151.11 (C-9), 145.97 (C-10b), 138.13 (C-10a), 132.44 (C-
7), 128.21 (C-5), 125.25 (C-6), 125.04 (C-6a), 123.40 (C-
8), 121.22 (C-4a), 119.89 (CN), 54.94 (C-3), 38.97 (C-4),
142.56, 131.34, 131.18, 129.99, 129.65, 126.23 (aromatic);
MS m/z (%): 405 (M++4, 1.52), 403 (M++2, 8.89), 401 (M+,
13.37) with a base peak at 256 (100); anal. calcd. for
C19H10Cl3N3O: C, 56.67; H, 2.50; N, 10.44. Found: C,
56.57; H, 2.38; N, 10.27 %.
2-amino-4-(3-chlorophenyl)-9-methyl-4H-pyrano[3,2-h]
2-amino-6-chloro-4-(4-bromophenyl)-4H-pyrano[3,2-h]
quinoline-3-carbonitrile (7b)
quinoline-3-carbonitrile (5i)
Yellow crystals from ethanol; yield 87 %; m.p. 236–238 °C;
IR (KBr, υmax cm−1): 3464, 3346, 3200 (NH2), 2188 (CN),
1655 (C=N); H NMR (500 MHz, DMSO-d6) δ: 8.19–7.09
(m, 8H, aromatic), 7.17 (bs, 2H, NH2), 4.97 (s, 1H, H-4),
2.69 (s, 3H, CH3); 13C NMR (125 MHz, DMSO-d6)
δ: 160.41 (C-2), 159.12 (C-9), 149.51 (C-10b), 137.09
Yellow crystals from ethanol; yield 86 %; m.p. 228-230 °C;
1
IR (KBr, υmax cm−1): 3445, 3330, 3182 (NH2), 2192 (CN),
1
1658 (C=N); H NMR (500 MHz, DMSO-d6) δ: 8.95–7.18
(m, 9H, aromatic), 7.25 (bs, 2H, NH2), 5.00 (s, 1H, H-4);
13C NMR (125 MHz, DMSO-d6) δ: 160.30 (C-2), 150.25