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U. P. PATIL ET AL.
2-Amino-4-(2-chlorophenyl)-5-oxo-4H,5H-pyrano[3,2-c]chromene-3-carbonitrile (5i)
Mp 275 ꢀC, lit mp 275-277 ꢀC;12 FT-IR (cmꢁ1): 3490, 3187, 2232, 1781, 1640, 1340,
1
1234, 834, 751; H NMR (300 MHz, DMSO-d6): d (ppm) 7.90-7.87 (q, 1H J ¼ 8.2 Hz),
7.72-7.66 (m, 1H), 7.50-7.41 (m, 4H), 7.33-7.28 (m, 2H), 7.14 (s, 2H), 4.47 (s, 1H); 13C-
NMR (75.46 MHz, DMSO-d6): d (ppm) 160.68, 159.91, 159.35, 152.42, 143.76, 132.34,
128.93, 128.65, 127.44, 126.89, 126.34, 125.33, 124.09, 119.86, 116.76, 115.07, 106.21,
58.91, 33.78; MS: m/z 350.0458 (100.0%); found: 350.0719.
Anal. Calcd for C19H11ClN2O3: C, 65.06; H, 3.16; N, 7.99. Found: C, 65.07; H, 3.14;
N, 7.99.
2-Amino-4-(4-fluorophenyl)-5-oxo-4H,5H-pyrano[3,2-c]chromene-3-carbonitrile (5j)
Mp 258 ꢀC, lit mp 256-258 ꢀC;12 FT-IR (cmꢁ1): 3321, 3082, 2201, 1745, 1658, 1365,
1
1211, 845, 730; H NMR (300 MHz, DMSO-d6): d (ppm) 7.91 (d, 1H J ¼ 7.6 Hz), 7.73-
7.68 (t, 1H J ¼ 7.5 Hz), 7.51-7.38 (m, 5H), 7.32-7.22 (m, 3H), 4.92 (s, 1H); 13C-NMR
(75.46 MHz, DMSO-d6): d (ppm) 160.22, 160.12, 159.87 (d, J ¼ 272.5 Hz, C-F), 159.46
(d, J ¼ 6.8 Hz, C-F), 153.01, 139.93, 129.34 (d, J ¼ 8.2 Hz, C-F), 128.38, 125.72, 123.51,
119.41, 116.72, 115.98 (d, J ¼ 21.7 Hz, C-F), 115.78 (d, J ¼ 21.7 Hz, C-F), 112.35, 105.69,
59.11, 33.76; MS: m/z 334.0754 (100.0%); found: 335.1341.
Anal. Calcd for C19H11FN2O3: C, 68.26; H, 3.32; N, 8.38. Found: C, 68.25; H, 3.30;
N, 8.37.
2-Amino-7-hydroxy-4-phenyl-4H-chromene-3-carbonitrile (6a)
Mp 233 ꢀC, lit mp 234-236 ꢀC;19 FT-IR (cmꢁ1): 3471, 3328, 3210, 2971, 2190, 1642,
1
1506, 1399, 1144, 847, 752; H NMR (300 MHz, DMSO-d6): d (ppm) 9.69 (s, 1H), 7.30
(t, 2H, J ¼ 7.1 Hz), 7.17 (m, 3H), 6.87 (s, 2H), 6.49 (d, 1H, J ¼ 7.6 Hz), 6.47 (d, 1H,
J ¼ 7.2 Hz), 6.41 (s, 1H), 4.61 (s, 1H); 13C-NMR (75.46 MHz, DMSO-d6): d (ppm)
160.29, 157.12, 148.90, 146.38, 129.95, 128.61, 127.40, 126.66, 120.71, 113.76, 112.43,
102.23, 56.36; MS: m/z 264.0899 (100.0%); found: 265.1308.
Anal. Calcd for C16H12N2O2: C, 72.72; H, 4.58; N, 10.60. Found: C, 72.71; H, 4.55;
N, 10.57.
2-Amino-7-hydroxy-4-(3-nitrophenyl)-4H-chromene-3-carbonitrile (6b)
Mp 188 ꢀC, lit mp 188-190 ꢀC;19 FT-IR (cmꢁ1): 3476, 3391, 3254, 2986, 2192, 1677,
1
1567, 1450, 1389, 1167, 878, 734; H NMR (300 MHz, DMSO-d6): d (ppm) 9.77 (1H),
8.02 (t, 2H, J ¼ 7.6 Hz), 7.64 (d, 2H, J ¼ 7.3 Hz), 7.01 (s, 2H), 6.84 (d, 1H, J ¼ 8.4 Hz),
6.45 (t, 2H, J ¼ 8.2 Hz), 4.90 (s, 1H); 13C-NMR (75.46 MHz, DMSO-d6): d (ppm) 160.51,
157.50, 148.94, 148.58, 147.97, 134.30, 130.32, 129.98, 121.85, 121.77, 120.38, 112.70,
112.55, 102.42, 56.07; MS: m/z 309.0750 (100.0%); found: 309.9762.
Anal. Calcd for C16H11N3O4: C, 62.14; H, 3.59; N, 13.59. Found: C, 62.12; H, 3.55;
N, 13.57.