6.80-7.72 (m, 14 aromatic H). 13C NMR spectrum, δ, ppm: 43.59 (CH2), 65.1 (ArCHN), 113.85, 119.62, 125.86,
127.45, 128.55, 128.93, 129.33, 130.04, 132.88, 133.51, 141.30, 145.09 (aromatic C), 150.0 (C=N). Mass-
spectrum, m/z (Irel, %): 379 [M+2]+ (80), 377 [M]+ (79), 91 (100). Found, %: C 66.87; H 4.54; N 7.43.
C21H17BrN2. Calculated, %: C 66.85; H 4.54; N 7.42.
5-(4-Bromophenyl)-3-(4-chlorophenyl)-1-phenyl-2-pyrazoline (4f). Yield 3.8 g, 93%, yellow powder;
1
mp 174-176°C. IR spectrum, ν, cm-1: 3029, 1594, 1495. H NMR spectrum, δ, ppm (J, Hz): 3.29 (1H, dd, J1 =
16.8, J2 = 7.2, CHAHBC=N); 4.02 (1H, dd, J1 = 16.8, J2 = 12.4, CHAHBC=N); 5.47 (1H, dd, J1 = 12.4, J2 = 7.2,
ArCHN); 7.04-7.87 (m, 13 aromatic H). 13C NMR spectrum, δ, ppm: 43.3 (CH2), 65.1 (ArCHN), 113.67, 119.75,
125.29, 126.87, 127.63, 128.75, 128.90, 130.16, 131.21, 132.31, 134.55, 141.45 (aromatic C), 149.2 (C=N).
Mass-spectrum, m/z (Irel, %): 415 [M+4]+ (25), 413 [M+2]+ (97), 411 [M]+ (82), 91 (100). Found, %: C 61.26; H
6.90; N 6.81. C21H16N2CLBr. Calculated, %: C 61.26; H 3.91; N 6.80.
5-(4-Methylphenyl)-1,3-diphenyl-2-pyrazoline (4g). Yield 1.9 g, 64%, yellow powder; mp 157-159°C.
1
IR spectrum, ν, cm-1: 3027, 1598, 1495. H NMR spectrum, δ, ppm (J, Hz): 2.91 (1H, dd, J1 = 17.2, J2 = 7.2,
CHAHBC=N); 3.59 (1H, dd, J1 = 17.2, J2 = 12.2, CHAHBC=N); 5.07 (1H, dd, J1 = 12.2, J2 = 7.2, ArCHN); 6.63-
13
7.47 (m, 14 aromatic H). C NMR spectrum, δ, ppm: 21.09 (CH3), 43.50 (CH2), 65.1 (ArCHN), 105.1, 113.9,
119.5, 125.9, 126.9, 127.4, 128.7, 129.1, 131.6, 134.4, 142.5, 145.0 (aromatic C), 148.2 (C=N). Mass-spectrum,
m/z (Irel, %): 312 [M]+ (77), 91 (100). Found, %: C 84.56; H 6.45; N 8.96. C22H20N2 Calculated, %: C 84.58; H
6.45; N 8.96.
3-(4-Chlorophenyl)-5-(4-methylphenyl)-1-phenyl-2-pyrazoline (4h). Yield 2.6 g, 76%, yellow
1
powder; mp 162-164°C. IR spectrum, ν, cm-1: 3037, 1593, 1490. H NMR spectrum, δ, ppm (J, Hz): 2.30 (3H,
s); 3.11 (1H, dd, J1 = 17.2, J2 = 7.2, CHAHBC=N); 3.78 (1H, dd, J1 = 17.2, J2 = 12.4, CHAHBC=N); 5.25 (1H, dd,
13
J1 = 12.4, J2 = 7.2, ArCHN); 6.66-7.69 (m, 16 aromatic). C NMR spectrum, δ, ppm: 21.0 (CH3) 43.50 (CH2),
64.7 (ArCHN), 113.70, 119.4, 125.8, 126.9, 128.7, 129.8, 131.6, 134.3, 137.3, 139.5, 144.9, 145.50 (aromatic
C), 149.5 (C=N). Mass-spectrum, m/z (Irel, %): 348 [M+2]+ (26), 346 [M]+ (78), 91 (100) Found, %: C 76.19;
H 5.52; N 8.10. C22H19ClN2. Calculated, %: C 76.18; H 5.52; N 8.07.
5-(4-Dimethylaminophenyl)-1,3-diphenyl-2-pyrazoline (4i). Yield 1.5 g, 45%, yellow powder; mp
161-163°C. IR spectrum, ν, cm-1: 3027, 1603, 1489. 1H NMR spectrum, δ, ppm (J, Hz): 2.96 (6H, s, 2CH3); 3.16
(1H, dd, J1 = 17.1, J2 = 7.2, CHAHBC=N); 3.81 (1H, dd, J1 = 17.1, J2 = 12.2, CHAHBC=N); 5.23 (1H, dd, J1 =
13
12.2, J2 = 7.2, ArCHN); 6.74-7.78 (m, 14 aromatic H). C NMR spectrum, δ, ppm: 40.50 (CH3) 43.7 (CH2),
64.6 (ArCHN), 113.4, 113.8, 119.0, 125.7, 126.8, 128.3, 128.4, 128.7, 131.0, 133.3, 145.4, 146.7 (aromatic C),
150.0 (C=N). Mass-spectrum, m/z (Irel, %): 341 [M]+ (81), 91 (100). Found, %: C 80.91; H 6.78; N 12.30.
C23H23N3. Calculated, %: C 80.90; H 6.78; N 12.30.
3-(4-Chlorophenyl)-5-(4-dimethylaminophenyl)-1-phenyl-2-pyrazoline (4j). Yield 2.6 g, 70%,
yellow powder; mp 167-169°C. IR spectrum, ν, cm-1: 3037, 1588, 1495. H NMR spectrum, δ, ppm (J, Hz): 2.95
(6H, s, 2CH3); 3.11 (1H, dd, J1 = 17.1, J2 = 7.2, CHAHBC=N); 3.75 (1H, dd, J1 = 17.1, J2 = 12.4, CHAHBC=N);
13
5.23 (1H, dd, J1 = 12.4, J2s = 7.2, ArCHN); 6.73-7.68 (m, 13 aromatic H). C NMR spectrum, δ, ppm: 40.50
(CH3) 43.5(CH2), 64.7(ArCHN), 113.4, 113.9, 119.3, 126.8, 127.8, 128.6, 128.7, 130.7, 131.9, 134.2, 145.2,
145.5, (aromatic C) 150.1 (C=N). Mass-spectrum, m/z (Irel, %): 377 [M+2]+ (28), 375 [M]+ (89), 91 (100).
Found, %: C 73.49; H 5.87; N 11.16. C23H22ClN3. Calculated, %: C 73.49; H 5.89; N 11.17.
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