U. P. Patil, R. C. Patil, and S. S. Patil
Vol 000
DMSO-d6): δ (ppm) 160.61, 156.01, 154.74, 135.50,
134.74, 128.42, 120.89, 115.09, 98.05, 57.79, 35.47, 9.73;
MS: m/z 268.0960 (100.0%); found: 268.0959. Elemental
analysis: Calcd. (%) for C14H12N4O2: C, 62.68; H, 4.51;
128.60, 128.29, 127.79, 127.11, 126.10, 119.63, 112.70,
97.01, 57.97, 12.61; MS: m/z 358.1430 (100.0%);
found: 358.1430. Elemental analysis: Calcd. (%) for
C21H18N4O2: C, 70.38; H, 5.06; N, 15.63. Found: C,
N, 20.88. Found: C, 62.67; H, 4.50; N, 20.86.
70.35; H, 5.05; N, 15.61.
6-Amino-4-(3-methoxyphenyl)-3-methyl-1,4-
6-Amino-3-methyl-4-(3-nitrophenyl)-1-phenyl-1,4-
dihydropyrano[2,3-c]pyrazole-5-carbonitrile (5n) [48]. State:
dihydropyrano[2,3-c]pyrazole-5-carbonitrile (5j) [47]. State:
solid; mp 212°C (lit. 211–213°C); FTIR (cmÀ1): 3321,
3310, 3170, 2187, 1670, 1661, 1512, 1457, 1364, 1292,
1131, 980, 780; 1H-NMR (300 MHz, DMSO-d6): δ
(ppm) 12.09 (s, 1H), 7.25 (t, 1H, J = 3.0 Hz), 6.88 (s,
2H), 6.80–6.77 (q, 1H, J = 7.9 Hz), 6.71 (s, 2H), 4.55 (s,
1H), 3.70 (s, 3H), 1.80 (s, 3H); 13C-NMR (75.46 MHz,
DMSO-d6): δ (ppm) 160.91, 159.23, 154.75, 146.10,
135.61, 129.56, 120.77, 119.67, 113.48, 11.65, 97.48,
57.07, 9.78; MS: m/z 282.1117 (100.0%); found:
282.1115. Elemental analysis: Calcd. (%) for
C15H14N4O2: C, 63.82; H, 5.00; N, 19.85. Found: C,
solid; mp 186°C (lit. 190–191°C); FTIR (cmÀ1): 3410,
3348, 3150, 2199, 1671, 1581, 1402, 1369, 1258, 1167,
1
962, 761; H-NMR (300 MHz, DMSO-d6): δ (ppm) 8.14
(s, 2H), 7.77 (m, 4H), 7.37 (m, 5H), 4.96 (s, 1H), 1.78 (s,
3H); 13C-NMR (75.46 MHz, DMSO-d6): δ (ppm) 160.41,
144.90, 144.42, 143.04, 138.14, 129.69, 128.63, 128.23,
127.89, 127.12, 126.80, 119.69, 112.73, 98.01, 58.47,
12.21; MS: m/z 373.1175 (100.0%); found: 373.1174.
Elemental analysis: Calcd. (%) for C20H15N5O3: C,
64.34; H, 4.05; N, 18.76. Found: C, 64.32; H, 4.05; N,
18.73.
63.81; H, 5.00; N, 19.83.
6-Amino-4-(2-chlorophenyl)-3-methyl-1,4-
dihydropyrano[2,3-c]pyrazole-5-carbonitrile (5k) [31]. State:
6-Amino-4-(2-chlorophenyl)-3-methyl-1-phenyl-1,4-
dihydropyrano[2,3-c]pyrazole-5-carbonitrile (5o) [48]. State:
solid; mp 146°C (lit. 145–146°C); FTIR (cmÀ1): 3462,
solid; mp 246°C (lit. 245–146°C); FTIR (cmÀ1): 3491,
3423, 3142, 2189, 1682, 1530, 1482, 1362, 1260, 1179,
951, 780; 1H-NMR (300 MHz, DMSO-d6): δ (ppm)
12.12 (s, 1H), 7.38 (q, 1H, J = 8.9 Hz), 7.27 (m, 2H),
7.18 (d, 1H, J = 7.2 Hz), 6.95 (s, 2H), 5.05 (s, 1H), 1.75
(s, 3H); 13C-NMR (75.46 MHz, DMSO-d6): δ (ppm)
161.40, 145.20, 143.45, 143.08, 138.11, 129.67, 128.60,
128.29, 127.79, 127.11, 126.10, 119.63, 112.70, 97.01,
57.97, 12.61; MS: m/z 286.0621 (100.0%); found:
286.0620. Elemental analysis: Calcd. (%) for
C14H11ClN4O: C, 58.65; H, 3.87; N, 19.54. Found: C,
3318, 3170, 2191, 1670, 1521, 1492, 1364, 1251, 1160,
932, 771; H-NMR (300 MHz, DMSO-d6): δ (ppm) 7.59
1
(m, 1H), 7.62–7.56 (t, 2H, J = 7.8 Hz), 7.48–7.7.37 (m,
2H), 7.24–7.16 (q, 4H J = 8.5 Hz), 6.76 (s, 2H), 4.69
(1H), 1.99 (s, 3H); 13C-NMR (75.46 MHz, DMSO-d6): δ
(ppm) 160.22, 144.70, 144.82, 143.24, 138.19, 130.11,
129.59, 128.73, 128.51, 128.42, 127.82, 127.62, 126.87,
119.63, 112.11, 98.34, 58.41, 12.03; MS: m/z 362.0934
(100.0%); found: 362.0933. Elemental analysis: Calcd.
(%) for C20H15ClN4O: C, 66.21; H, 4.17; N, 15.44.
Found: C, 66.20; H, 4.15; N, 15.43.
6-Amino-4-(4-hydroxyphenyl)-3-methyl-1-phenyl-1,4-
dihydropyrano[2,3-c]pyrazole-5-carbonitrile (5p) [48]. State:
58.63; H, 3.84; N, 19.54.
6-Amino-3-methyl-1,4-diphenyl-1,4-dihydropyrano[2,3-c]
solid; mp 210°C (lit. 210–212°C); FTIR (cmÀ1): 3392,
pyrazole-5-carbonitrile (5l) [48].
State: solid; mp 167°C
(lit. 170–171°C); FTIR (cmÀ1): 3451, 3304, 3172, 2197,
1676, 1662, 1540, 1452, 1324, 1272, 1137, 982, 820;
1H-NMR (300 MHz, DMSO-d6): δ (ppm) 7.76 (s, 1H),
7.48–7.22 (m, 11H), 4.67 (s, 1H), 1.76 (s, 3H); 13C-NMR
(75.46 MHz, DMSO-d6): δ (ppm) 159.40, 145.23,
143.85, 143.58, 137.51, 129.30, 128.80, 128.49, 127.75,
127.01, 126.13, 119.93, 112.72, 98.01, 58.17, 12.53; MS:
m/z 329.1324 (100.0%); found: 329.1323. Elemental
analysis: Calcd. (%) for C20H16N4O: C, 73.15; H, 4.91;
3302, 3165, 2202, 1675, 1528, 1462, 1362, 1259, 1168,
937, 818; H-NMR (300 MHz, DMSO-d6): δ (ppm) 9.34
1
(s, 1H), 7.78 (d, 2H, J = 7.8 Hz), 7.50–7.44 (t, 2H,
J = 8.5 Hz), 7.32–7.27 (t, 1H, J = 7.2 Hz), 7.13 (s, 2H),
7.03–7.01 (d, 2H, J = 8.1 Hz), 6.71 (s, 2H), 4.54 (s, 1H),
1.77 (s, 3H); 13C-NMR (75.46 MHz, DMSO-d6): δ
(ppm); 159.17, 156.27, 145.34, 143.64, 143.26, 137.58,
133.91, 129.29, 128.74, 126.04, 120.09, 119.85, 115.19,
99.02, 58.80, 12.57; MS: m/z 344.1273 (100.0%); found:
344.1272. Elemental analysis: Calcd. (%) for
C20H16N4O2: C, 69.76; H, 4.68; N, 16.27. Found: C,
N, 17.06. Found: C, 73.12; H, 4.90; N, 17.04.
6-Amino-4-(4-methoxyphenyl)-3-methyl-1-phenyl-1,4-
dihydropyrano[2,3-c]pyrazole-5-carbonitrile (5m) [48].
69.75; H, 4.68; N, 16.26.
State: solid; mp 173°C (lit. 174–176°C); FTIR (cmÀ1):
3420, 3398, 3156, 2190, 1678, 1521, 1409, 1359, 1250,
1107, 982, 781; 1H-NMR (300 MHz, DMSO-d6): δ
(ppm) 7.78 (d, 2H, J = 7.8 Hz), 7.47 (t, 2H,
J = 7.5 Hz), 7.32 (t, 1H, J = 7.1 Hz), 7.16 (d, 4H,
J = 7.8 Hz), 6.90 (s, 2H), 4.61 (s, 1H), 3.73 (s, 3H),
1.77 (s, 3H); 13C-NMR (75.46 MHz, DMSO-d6): δ
(ppm) 161.40, 145.20, 143.45, 143.08, 138.11, 129.67,
6-Amino-4-(4-chlorophenyl)-3-methyl-1-phenyl-1,4-
dihydropyrano[2,3-c]pyrazole-5-carbonitrile (5q) [48]. State:
solid; mp 176°C (lit. 175–176°C); FTIR (cmÀ1): 3412,
3356, 3111, 2192, 1674, 1527, 1463, 1361, 1258, 1167,
1
935, 734; H-NMR (300 MHz, DMSO-d6): δ (ppm) 7.77
(d, 2H, J = 6.3 Hz), 7.48–7.26 (m, 9H), 4.71 (s, 1H),
1.77 (s, 3H); 13C-NMR (75.46 MHz, DMSO-d6): δ (ppm)
159.12, 156.57, 145.30, 143.72, 143.38, 137.55, 133.81,
Journal of Heterocyclic Chemistry
DOI 10.1002/jhet