262
H. SHEIBANI AND M. BABAIE
was removed by evaporation and poured into ice-cold water; the crude product was
filtered, dried, and recrystallized from 96% ethanol.
6-Amino-4-(4-chlorophenyl)-1-phenyl-3-propyl-1,4-dihydropyrano[2,3-c]-
pyrazol-5-yl cyanide (4g). Pale yellow crystals (0.71 g), yield 0.92%; mp
ꢁ1
181–182ꢀC; nmax (KBr): 3456, 3312 (NH2), 2210 (CN), 1656 (C N), 1586 (Ar) cm
;
=
dH (500 MHz, DMSO-d6): 7.83–7.30 (9H, m, arom), 7.24 (2H, s, NH2), 4.73 (1H, s,
CH), 2.14 (1H, m, Ha on C1 of propyl), 2.05(1H, m, Hb on C1 of propyl), 3.5 (1H, m,
Ha on C2 of propyl), 1.22 (1H, m, Hb on C2 of propyl), 1.83 (3H, t, CH3); dC
(125 MHz, DMSO-d6) 160.20 (C6), 146.82, 144.74, 143.87, 183.40, 132.45, 130.60,
130.19, 129.36, 127.10, 120.97, 120.73, 98.64 (CN), 58.82 (C5), 39.90 (C4), 9.73,
21.56, 14.51. MS, m=z (%): 390 (Mþ, 15), 324 (10), 280 (23), 279 (100), 127 (10),
77 (65). Anal. calcd. for C22H19ClN4O: C, 67.60; H, 4.90; N, 14.33%. Found: C,
67.39; H, 4.78; N, 14.03.
6-Amino-4-(4-chlorophenyl)-3-isopropyl-1-phenyl-1,4-dihydropyrano[2,
3-c]pyrazol-5-yl cyanide (4h). Pale yellow crystals (0.72 g), yield 0.93%, mp
172–173ꢀC, nmax (KBr): 3456, 3312 (NH2), 2210 (CN), 1656 (C N), 1586 (Ar)
=
cmꢁ1; dH (500 MHz, DMSO-d6): 7.80 (2H, d, JHH ¼ 8.05 Hz, CH), 7.50 (2H, t,
3
3
3JHH ¼ 7.7 Hz, CH, arom), 7.41 (2H, d, JHH ¼ 8.39 Hz, CH, arom), 7.33 (2H, t,
3
3JHH ¼ 7.44 Hz, CH, arom), 7.31 (2H, d, JHH ¼ 8.05 Hz, CH, arom), 7.22 (2H,
3
s, NH2), 4.77 (1H, s, CH), 2.44 (1H, m, CH),1.02 (3H, d, JHH ¼ 6.95, CH3), 0.85
(3H,d,3JHH ¼ 6.88, CH3), (125 MHz, DMSO-d6) 160.00 (C6), 154.60, 144.86,
144.17, 138.44, 132.45, 130.61, 130.18, 129.39, 127.11, 121.07, 120.72, 97.77 (CN),
59.10 (C5), 39.90 (C4), 37.22, 27.72, 22.34, 21.31. MS, m=z (%): 390 (Mþ, 17), 324
(17), 280 (30), 279 (100), 127 (25), 77 (70). Anal. calcd. for C22H19ClN4O: C,
67.60; H, 4.90; N, 14.33%. Found: C, 67.31; H, 4.74; N, 14.06.
6-Amino-4-(2,4-dichlorophenyl)-3-isopropyl-1-phenyl-1,4-dihydropyr-
ano[2,3-c]pyrazol-5-yl cyanide (4i). White crystals (0.8 g), yield 0.95%, mp
188–189ꢀC, nmax (KBr): 3438, 3321, 3204 (NH2), 2197 (CN), 1659 (C N), 1589
=
(Ar) cmꢁ1; dH (500 MHz, DMSO-d6): 7.81–7.32 (8H, m, arom), 7.31 (2H, s, NH2),
3
5.21 (1H, s, CH), 2.43 (1H, m,CH), 1.03 (3H, d, JHH ¼ 6.95, CH3), 0.86 (3H, d,
3JHH ¼ 6.88, CH3), dC (125 MHz, DMSO-d6) 160.12 (C6), 154.02, 144.40, 143.56,
143.02, 138.38, 132.55, 130.40, 130.28, 130.02, 129.30, 127.19, 121.12, 104.50
(CN), 58.34 (C5), 38.01 (C4), 27.91, 22.26, 21.31. MS, m=z (%): 425 (Mþ, 12), 361
(22), 335 (27), 314(100), 77 (76). Anal. calcd. for C22H18Cl2N4O: C, 62.13; H,
4.27; N, 13.17%. Found: C, 61.81; H, 4.16; N, 12.88.
Knoevenagel Condensation
General procedure for the preparation of arylidenemalononitriles
Ia–c. The reactions were carried out in a standard round-bottom glass flask
equipped with a vertical condenser under thermal conditions. Reactions were
performed with arylaldehydes 1 (2 mmol), malononitrile 2 (2 mmol), and MgO
(0.05 g) in acetonitrile (40 mL) as solvent, refluxed with stirring for the specified time
(Table 1).