3.3. Procedure for the Preparation of 1-(3,4-Dimethylphenyl)-3-Phenyl-5-(4-Alkoxyphenyl)-2-Pyrazolines 1h–12h
Synthesis of 1-(3,4-dimethylphenyl)-3-phenyl-5-(4-alkoxyphenyl)-2-pyrazolines was carried out by dissolving the 4-alkoxychalcones 1b–12b (0.01 moles) in glacial acetic acid (25 mL) containing a few drops of concentrated hydrochloric acid and were heated to 60–65 °C for 30 minutes. (3,4-Dimethylphenyl)hydrazaine hydrochloride (0.02 mole, 3.45 g) was added to the reaction flask and the resulting mixture heated to reflux for 5–8 hours. The reaction mixture was cooled to room temperature and poured onto crushed ice to obtain the products. The precipitates obtained were filtered, washed with distilled water and dried in a desicator and were purified by column chromatography using silica gel and petroleum ether/ethyl acetate (4:1) as mobile phase. Purification of all the synthesized compounds was achieved by recrystallization and purity of each compound was monitored by thin layer (tlc) and gas (gc) chromatography.
1-(3,4-Dimethylphenyl)-3-phenyl-5-(4-methoxyphenyl)-2-pyrazoline (1h). 3-(4-Methoxyphenyl)-1-phenylprop-2-en-1-one (2.38 g, 10 mmol) and (3,4-dimethylphenyl) hydrazaine (2.72 g, 20 mmol) were reacted according to the general procedure. Color pale yellow solid; yield 80% (1.90 g); m.p. 120–124 °C; Rf = 0.88 (petroleum ether-ethyl acetate, 4:1), FT-IR (KBr, cm−1): 1682, 1292, 1497, 1257, 1047, 1H-NMR (300 MHz, CDCl3) δ 2.17 (s, 3H, N-Ar-4-CH3), 2.22 (s, 3H, N-Ar-3-CH3), 3.11 (dd, 1H, J = 7.8, 17.1 Hz, Ha), 3.75 (s, 3H, -O-CH3), 3.80 (dd, 1H, J = 12.3, 16.8 Hz, Hb), 5.20 (dd, 1H, J = 7.5, 12.3 Hz, Hx), 6.71 (d, 1H, J = 8.4 Hz, N-ArHh), 6.87 (d, 2H, J = 8.7 Hz, ArHc=c’), 6.93 (d, 1H, J = 8.4 Hz, N-ArHi), 7.06 (s, 1H, N-ArHj), 7.27 (d, 2H, J = 8.7 Hz, ArHd=d’), 7.33−7.43 (m, 3H, ArHf=f’, g), 7.74(d, 2H, J = 8.4 Hz, ArHe=e’), 13C-NMR (75 MHz, CDCl3) δ 18.8, 20.2, 43.5, 55.2, 64.2, 110.7, 114.4 (2C), 115.1, 125.6 (2C), 127.0 (2C), 128.3, 128.5 (2C), 129.8, 132.9, 134.9, 137.0, 143.1, 146.1, 158.8, 162.6 EIMS: m/z 356 (M+, base peak). Anal. Calcd. For C24H24N2O (Mol. Wt. 356): C, 80.87; H, 6.79; N, 7.86; Found: C, 80.81; H, 6.73; N, 7.92%.
1-(3,4-Dimethylphenyl)-3-phenyl-5-(4-ethoxyphenyl)-2-pyrazoline (2h). 3-(4-Ethoxyphenyl)-1-phenyl-prop-2-en-1-one (2.52 g, 10 mmol) and (3,4-dimethylphenyl) hydrazaine (2.72 g, 20 mmol) were reacted according to the general procedure. Color pale yellow solid; yield 85% (2.14 g); m.p. 102–106 °C; Rf = 0.85 (petroleum ether-ethyl acetate, 4:1), FT-IR (KBr, cm−1): 1685, 1297, 1495, 1255, 1043, 1H-NMR (300 MHz, CDCl3) δ 1.42 (t, 3H, J = 7.0 Hz, −O−CH2−CH3), 2.17 (s, 3H, N- Ar-4-CH3), 2.22 (s, 3H, N-Ar-3-CH3), 3.11 (dd, 1H, J = 7.8, 17.1 Hz, Ha), 3.80 (dd, 1H, J = 12.3, 16.8 Hz, Hb), 4.02 (q, 2H, J = 7.2 Hz, −O−CH2−), 5.20 (dd, 1H, J = 7.5, 12.3 Hz, Hx), 6.72 (d, 1H, J = 8.4 Hz, N-ArHh), 6.87 (d, 2H, J = 8.7 Hz, ArHc=c’), 6.93 (d, 1H, J = 8.4 Hz, N- ArHi), 7.06 (s, 1H, N-ArHj), 7.25 (d, 2H, J = 8.7 Hz, ArHd=d’), 7.31-7.43 (m, 3H, ArHf=f’, g), 7.75(d, 2H, J = 8.4 Hz, ArHe=e’), 13C-NMR (75 MHz, CDCl3) δ 14.8, 18.8, 20.2, 43.5, 63.4, 64.3, 110.7, 114.9, 115.1, 125.6 (2C), 127.0 (2C), 127.1, 128.3, 128.5, 129.8, 133.0, 134.8, 137.4, 143.2, 146.1, 158.2, EIMS: m/z 370 (M+, base peak). Anal. Calcd. For C25H26N2O (Mol. Wt. 370): C, 81.05; H, 7.07; N, 7.56; Found: C, 81.01; H, 7.02; N, 7.64%.
1-(3,4-Dimethylphenyl)-3-phenyl-5-(4-propyloxyphenyl)-2-pyrazoline (3h). 3-(4-Propyloxyphenyl)-1-phenylprop-2-en-1-one (2.66 g, 10 mmol) and (3,4-dimethylphenyl) hydrazaine (2.72 g; 20 mmol) were reacted according to the general procedure. Color pale yellow solid; yield 81% (2.15 g); m.p. 126–130 °C; Rf = 0.87 (petroleum ether-ethyl acetate, 4:1), FT-IR (KBr, cm−1): 1687, 1299, 1493, 1254, 1042, 1H-NMR (300 MHz, CDCl3) δ 1.04 (t, 3H, J = 7.2 Hz, −O−CH2−CH2−CH3), 1.81 (sextet, 2H, J = 7.2 Hz, −O−CH2−CH2−CH3), 2.17 (s, 3H, N-Ar-4-CH3), 2.22 (s, 3H, N-Ar-3-CH3), 3.11 (dd, 1H, J = 7.5, 16.8 Hz, Ha), 3.80 (dd, 1H, J = 12.3, 16.8 Hz, Hb), 3.90 (t, 2H, J = 6.6 Hz, −O−CH2−), 5.20 (dd, 1H, J = 7.5, 12.3 Hz, Hx), 6.72 (d, 1H, J = 8.4 Hz, N-ArHh), 6.87 (d, 2H, J = 8.7 Hz, ArHc=c’), 6.93 (d, 1H, J = 8.4 Hz, N-ArHi), 7.06 (s, 1H, N-ArHj), 7.25 (d, 2H, J = 8.7 Hz, ArHd=d’), 7.33-7.43 (m, 3H, ArHf= f’, g), 7.74(d, 2H, J = 8.4 Hz, ArHe=e’); 13C-NMR (75 MHz, CDCl3) δ 10.5, 18.8, 20.2, 22.6, 43.6, 64.3, 69.4, 110.7, 114.9 (2C), 115.1, 125.6 (2C), 127.0 (2C), 127.1, 128.3, 128.5 (2C), 129.8, 133.0, 134.7, 137.0, 143.1, 146.1, 158.4, EIMS: m/z 384 (M+, base peak). Anal. Calcd. For C26H28N2O (Mol. Wt. 384): C, 81.21; H, 7.34; N, 7.29; Found: C, 81.16; H, 7.31; N, 7.37%.
1-(3,4-Dimethylphenyl)-3-phenyl-5-(4-butyloxyphenyl)-2-pyrazoline (4h). 3-(4-Butyloxyphenyl)-1-phenylprop-2-en-1-one (2.80 g, 10 mmol) and (3,4-dimethylphenyl) hydrazaine (2.72 g, 20 mmol) were reacted according to the general procedure. Color pale yellow solid; yield 86% (2.40 g); m.p. 122–125 °C; Rf = 0.87 (petroleum ether-ethyl acetate, 4:1), FT-IR (KBr, cm−1): 1680, 1294, 1494, 1258, 1052, 1H-NMR (300 MHz, CDCl3) δ 0.99 (t, 3H, J = 7.2 Hz, −O−(CH2)3−CH3), 1.50 (sextet, 2H, J = 7.8 Hz, −O−CH2−CH2−CH2− CH3), 1.77 (qn, 2H, J = 8.0 Hz, −O−CH2−CH2−C2H5), 2.17 (s, 3H, N-Ar-4-CH3), 2.22 (s, 3H, N-Ar-3-CH3), 3.11 (dd, 1H, J = 7.5, 16.8 Hz, Ha), 3.80 (dd, 1H, J = 12.3, 16.8 Hz, Hb), 3.95 (t, 2H, J = 6.6 Hz, −O−CH2−), 5.20 (dd, 1H, J = 7.5, 12.3 Hz, Hx), 6.72 (d, 1H, J = 8.0 Hz, N-ArHh), 6.87 (d, 2H, J = 8.7 Hz, ArHc=c’), 6.93 (d, 1H, J = 8.1 Hz, N-ArHi), 7.06 (s, 1H, N-ArHj), 7.25 (d, 2H, J = 8.7 Hz, ArHd=d’), 7.33-7.43 (m, 3H, ArHf=f’, g), 7.75(d, 2H, J = 8.4 Hz, ArHe=e’); 13C-NMR (75 MHz, CDCl3) δ 13.9, 18.8, 19.2, 20.2, 31.3, 43.60, 64.3, 67.6, 110.7, 114.9 (2C), 115.1, 125.6 (2C), 127.0 (2C), 127.1, 128.3, 128.5 (2C), 129.8, 133.0, 134.7, 137.0, 143.1, 146.1, 158.4; EIMS: m/z 398 (M+, base peak). Anal. Calcd. For C27H30N2O (Mol. Wt. 398): C, 81.37; H, 7.59; N, 7.03; Found: C, 81.31; H, 7.55; N, 7.13%.
1-(3,4-Dimethylphenyl)-3-phenyl-5-(4-pentyloxyphenyl)-2-pyrazoline (5h). 3-(4-Pentyloxyphenyl)-1-phenylprop-2-en-1-one (2.94 g, 10 mmol) and (3,4-dimethylphenyl) hydrazaine (2.72 g, 20 mmol) were reacted according to the general procedure. Color pale yellow solid; yield 84% (2.46 g); m.p. 121–125 °C; Rf = 0.89 (petroleum ether-ethyl acetate, 4:1), FT-IR (KBr, cm−1): 1686, 1296, 1491, 1256, 1054, 1H-NMR (300 MHz, CDCl3) δ 0.94 (t, 3H, J = 7.2 Hz, −O−(CH2)4−CH3), 1.38−1.46 (m, −O−CH2−CH2−(CH2)2− CH3), 1.78 (qn, 2H, J = 7.2 Hz, −O−CH2−CH2−C3H7), 2.17 (s, 3H, N-Ar-4-CH3), 2.22 (s, 3H, N-Ar-3-CH3) , 3.11 (dd, 1H, J = 7.8, 17.1 Hz, Ha), 3.80 (dd, 1H, J = 12.3, 17.1 Hz, Hb), 3.94 (t, 2H, J = 6.6 Hz, −O−CH2−), 5.20 (dd, 1H, J = 7.5, 12.3 Hz, Hx), 6.72 (d, 1H, J = 8.1 Hz, N-ArHh), 6.86 (d, 2H, J = 8.7 Hz, ArHc=c’), 6.93 (d, 1H, J = 8.1 Hz, N-ArHi), 7.06 (s, 1H, N-ArHj), 7.25 (d, 2H, J = 8.7 Hz, ArHd=d’), 7.32-7.43 (m, 3H, ArHf=f’, g), 7.74(d, 2H, J = 8.1 Hz, ArHe=e’); 13C-NMR (75 MHz, CDCl3) δ 14.0, 18.8, 20.2, 22.4, 28.2, 28.9, 43.6, 64.3, 67.9, 110.7, 114.9, 115.1, 125.6, 127.0, 127.1, 128.3, 128.5, 129.8, 133.0, 134.7, 137.0, 143.1, 146.1, 158.4; EIMS: m/z 412 (M+, base peak). Anal. Calcd. For C28H32N2O (Mol. Wt. 412): C, 81.51; H, 7.82; N, 6.79; Found: C, 81.48; H, 7.79; N, 6.85%.
1-(3,4-Dimethylphenyl)-3-phenyl-5-(4-hexyloxyphenyl)-2-pyrazoline (6h). 3-(4-Hexyloxyphenyl)-1-phenylprop-2-en-1-one (3.08 g, 10 mmol) and (3,4-dimethylphenyl) hydrazaine (2.72 g, 20 mmol) were reacted according to the general procedure. Color pale yellow solid; yield 87% (2.67 g); m.p. 88–93 °C Rf = 0.87 (petroleum ether-ethyl acetate, 4:1), FT- IR (KBr, cm−1): 1679, 1292, 1497, 1258, 1048, 1H-NMR (300 MHz, CDCl3) δ 0.92 (t, 3H, J = 7.2 Hz, −O−(CH2)5−CH3), 1.32−1.48 (m, 6H, −O−CH2−CH2−(CH2)3− CH3), 1.78 (qn, 2H, J = 7.2 Hz, −O−CH2−CH2−C4H9), 2.16 (s, 3H, N-Ar-4- CH3), 2.22 (s, 3H, N-Ar-3-CH3), 3.11 (dd, 1H, J = 7.5, 16.8 Hz, Ha), 3.80 (dd, 1H, J = 12.3, 17.1 Hz, Hb), 3.93 (t, 2H, J = 6.6 Hz, −O−CH2−), 5.20 (dd, 1H, J = 7.0, 12.0 Hz, Hx), 6.71 (d, 1H, J = 8.1 Hz, N- ArHh), 6.86 (d, 2H, J = 8.7 Hz, ArHc=c’), 6.93 (d, 1H, J = 8.1 Hz, N-ArHi), 7.06 (s, 1H, N-ArHj), 7.25 (d, 2H, J = 8.7 Hz, ArHd=d’), 7.32-7.43 (m, 3H, ArHf=f’, g), 7.74(d, 2H, J = 8.1 Hz, ArHe=e’); 13C-NMR (75 MHz, CDCl3) δ 14.0, 18.8, 20.2, 22.6, 25.7, 29.2, 31.6, 43.6, 64.3, 68.0, 110.7, 114.9, 115.1, 125.6, 127.0, 127.1, 128.3, 128.5, 129.8, 133.0, 134.7, 137.0, 143.1, 146.1, 158.4; EIMS: m/z 426 (M+, base peak). Anal. Calcd. For C29H34N2O (Mol. Wt. 426): C, 81.65; H, 8.03; N, 6.57; Found: C, 81.65; H, 8.03; N, 6.57%.
1-(3, 4-Dimethylphenyl)-3-phenyl-5-(4-heptyloxyphenyl)-2-pyrazoline (7h). 3-(4-Heptyloxyphenyl)-1-phenylprop-2-en-1-one (3.22 g, 10 mmol) and (3,4-dimethylphenyl) hydrazaine (2.72 g, 20 mmol) were reacted according to the general procedure. Color pale yellow solid; yield 83% (2.67 g); m.p. 93–97 °C; Rf = 0.85 (petroleum ether-ethyl acetate, 4:1), FT-IR (KBr, cm−1): 1677, 1294, 1488, 1257, 1043, 1H-NMR (300 MHz, CDCl3) δ 0.91 (t, 3H, J = 7.2 Hz, −O−(CH2)6−CH3), 1.31−1.48 (m, 8H, −O−CH2−CH2−(CH2)4− CH3), 1.77 (qn, 2H, J = 7.8 Hz, −O−CH2−CH2−C5H11), 2.16 (s, 3H, N-Ar-4-CH3), 2.21 (s, 3H, N-Ar-3-CH3), 3.11 (dd, 1H, J = 7.8, 17.1 Hz, Ha), 3.80 (dd, 1H, J = 12.3, 17.1 Hz, Hb), 3.93 (t, 2H, J = 6.6 Hz, −O−CH2−), 5.20 (dd, 1H, J = 7.5, 12.3 Hz, Hx), 6.71 (d, 1H, J = 8.4 Hz, N-ArHh), 6.86 (d, 2H, J = 8.7 Hz, ArHc=c’), 6.92 (d, 1H, J = 8.1 Hz, N-ArHi), 7.05 (s, 1H, N-ArHj), 7.24 (d, 2H, J = 8.7 Hz, ArHd=d’), 7.32-7.42 (m, 3H, ArHf=f’, g), 7.74(d, 2H, J = 8.1 Hz, ArHe=e’); 13C-NMR (75 MHz, CDCl3) δ 14.1, 18.8, 20.1, 22.6, 26.0, 29.2, 31.7, 34.7, 43.5, 64.3, 68.0, 110.7, 114.9, 115.1, 125.6, 127.0, 127.1, 128.3, 128.5, 129.8, 133.0, 134.7, 137.0, 143.1, 146.1, 158.4; EIMS: m/z 440 (M+, base peak). Anal. Calcd. For C30H36N2O (Mol. Wt. 440): C, 81.78; H, 8.24; N, 6.36; Found: C, 81.72; H, 8.18; N, 6.43%.
1-(3,4-Dimethylphenyl)-3-phenyl-5-(4-octyloxyphenyl)-2-pyrazoline (8h). 3-(4-Octyloxyphenyl)-1-phenylprop-2-en-1-one (3.36 g, 10 mmol) and (3,4-dimethylphenyl) hydrazaine (2.72 g, 20 mmol) were reacted according to the general procedure. Color pale yellow solid; yield 86% (2.88 g); m.p. 96–99 °C; Rf = 0.87 (petroleum ether-ethyl acetate, 4:1), FT-IR (KBr, cm−1): 1685, 1298, 1491, 1253, 1057, 1H-NMR (300 MHz, CDCl3) δ 0.91 (t, 3H, J = 7.2 Hz, −O−(CH2)7−CH3), 1.30−1.45 (m, 10H, −O−CH2−CH2−(CH2)5− CH3), 1.78 (qn, 2H, J = 8.0 Hz, −O−CH2−CH2−C6H13), 2.16 (s, 3H, N-Ar-4- CH3), 2.21 (s, 3H, N-Ar-3-CH3), 3.11 (dd, 1H, J = 7.8, 17.1 Hz, Ha), 3.80 (dd, 1H, J = 12.3, 17.1 Hz, Hb), 3.93 (t, 2H, J = 6.6 Hz, −O−CH2−), 5.20 (dd, 1H, J = 7.5, 12.0 Hz, Hx), 6.71 (d, 1H, J = 8.1 Hz, N-ArHh), 6.86 (d, 2H, J = 8.7 Hz, ArHc=c’), 6.93 (d, 1H, J = 8.1 Hz, N-ArHi), 7.06 (s, 1H, N-ArHj), 7.25 (d, 2H, J = 8.7 Hz, ArHd=d’), 7.32–7.45 (m, 3H, ArHf=f’, g), 7.74(d, 2H, J = 8.4 Hz, ArHe=e’); 13C- NMR (CDCl3) δ 14.1, 18.8, 20.2, 22.6, 26.0, 29.2, 29.3, 31.8, 35.5, 43.5, 64.3, 67.9, 110.7, 114.9 (2C), 115.1, 125.6 (2C), 127.0 (2C), 127.1, 128.3, 128.5 (2C), 129.8, 132.9, 134.7, 137.0, 143.1, 146.1, 158.4; EIMS: m/z 454 (M+, base peak). Anal. Calcd. For C31H38N2O (Mol. Wt. 454): C, 81.89; H, 8.42; N, 6.16; Found: C, 81.85; H, 8.38; N, 6.25%.
1-(3,4-Dimethylphenyl)-3-phenyl-5-(4-nonyloxyphenyl)-2-pyrazoline (9h). 3-(4-Nonyloxyphenyl)-1-phenylprop-2-en-1-one (3.50 g, 10 mmol) and (3,4-dimethylphenyl) hydrazaine (2.72 g, 20 mmol) were reacted according to the general procedure. Color pale yellow solid; yield 85% (2.97 g); m.p. 101–103 °C; Rf = 0.85 (petroleum ether-ethyl acetate, 4:1), FT-IR (KBr, cm−1): 1679, 1292, 1493, 1254, 1055, 1H-NMR (300 MHz, CDCl3) δ 0.90 (t, 3H, J = 7.2 Hz, −O−(CH2)8−CH3), 1.30−1.47 (m, 12H, −O−CH2−CH2−(CH2)6− CH3), 1.78 (qn, 2H, J = 7.8 Hz, −O−CH2−CH2−C7H15), 2.17 (s, 3H, N-Ar-4- CH3), 2.22 (s, 3H, N-Ar-3-CH3), 3.11 (dd, 1H, J = 7.5, 16.8 Hz, Ha), 3.80 (dd, 1H, J = 12.3, 17.1 Hz, Hb), 3.93 (t, 2H, J = 6.6 Hz, −O−CH2−), 5.20 (dd, 1H, J = 7.5, 12.3 Hz, Hx), 6.71 (d, 1H, J = 8.1 Hz, N-ArHh), 6.87 (d, 2H, J = 8.7 Hz, ArHc=c’), 6.93 (d, 1H, J = 8.1 Hz, N-ArHi), 7.06 (s, 1H, N-ArHj), 7.25 (d, 2H, J = 8.7 Hz, ArHd=d’), 7.33-7.43 (m, 3H, ArHf=f’, g), 7.75(d, 2H, J = 8.4 Hz, ArHe=e’); 13C-NMR (75 MHz, CDCl3) δ 14.1, 18.8, 20.2, 22.7, 26.0, 29.3 (2C), 29.4, 29.5, 31.9, 43.6, 64.3, 67.9, 110.7, 114.9, 115.1, 125.6, 127.0, 127.1, 128.3, 128.5, 129.8, 133.0, 134.7, 137.0, 143.1, 146.1, 158.4; EIMS: m/z 468 (M+, base peak). Anal. Calcd. For C32H40N2O (Mol. Wt. 468): C, 82.01; H, 8.60; N, 5.98; Found: C, 81.97; H, 8.57; N, 6.05%.
1-(3,4-Dimethylphenyl)-3-phenyl-5-(4-decyloxyphenyl)-2-pyrazoline (10h). 3-(4-Decyloxyphenyl)-1-phenylprop-2-en-1-one (3.64 g, 10 mmol) and (3,4-dimethylphenyl) hydrazaine (2.72 g, 20 mmol) were reacted according to the general procedure. Color pale yellow solid; yield 81% (2.94 g); m.p. 85–87 °C; Rf = 0.86 (petroleum ether-ethyl acetate, 4:1), FT-IR (KBr, cm−1): 1687, 1297, 1498, 1259, 1049, 1H-NMR (300 MHz, CDCl3) δ 0.90 (t, 3H, J = 7.2 Hz, −O−(CH2)9−CH3), 1.30−1.47 (m, 14H, −O−CH2−CH2−(CH2)7− CH3), 1.78 (qn, 2H, J = 7.2 Hz, −O−CH2−CH2−C8H17), 2.16 (s, 3H, N-Ar-4- CH3), 2.20 (s, 3H, N-Ar-3-CH3), 3.11 (dd, 1H, J = 7.5, 17.1 Hz, Ha), 3.80 (dd, 1H, J = 12.3, 17.1 Hz, Hb), 3.93 (t, 2H, J = 6.6 Hz, −O−CH2−), 5.20 (dd, 1H, J = 7.5, 12.0 Hz, Hx), 6.71 (d, 1H, J = 8.1 Hz, N-ArHh), 6.86 (d, 2H, J = 8.7 Hz, ArHc=c’), 6.92 (d, 1H, J = 8.1 Hz, N-ArHi), 7.06 (s, 1H, N-ArHj), 7.25 (d, 2H, J = 8.7 Hz, ArHd=d’), 7.32-7.47 (m, 3H, ArHf=f’, g), 7.74(d, 2H, J = 8.4 Hz, ArHe=e’); 13C- NMR (75 MHz, CDCl3) δ 14.1, 18.8, 20.2, 22.7, 26.0, 29.2, 29.3, 29.4, 29.5, 29.6, 31.9, 43.5, 64.3, 68.0, 110.7, 114.9 (2C), 115.1, 125.6 (2C), 127.0, 127.1, 128.3, 128.5 (2C), 129.8, 133.0, 134.7, 137.0, 143.1, 146.1, 158.4; EIMS: m/z 482 (M+, base peak). Anal. Calcd. For C33H42N2O (Mol. Wt. 482): C, 82.11; H, 8.77; N, 5.80; Found: C, 82.09; H, 8.74; N, 5.88%.
1-(3,4-Dimethylphenyl)-3-phenyl-5-(4-undecyloxyphenyl)-2-pyrazoline (11h). 3-(4-Unecyloxyphenyl)-1-phenylprop-2-en-1-one (3.76 g, 10 mmol) and (3,4-dimethylphenyl) hydrazaine (2.72 g, 20 mmol) were reacted according to the general procedure. Color pale yellow solid; yield 87% (3.27 g); m.p. 88–92 °C; Rf = 0.85 (petroleum ether-ethyl acetate, 4:1), FT-IR (KBr, cm−1): 1689, 1295, 1494, 1256, 1054, 1H-NMR (300 MHz, CDCl3) δ 0.90 (t, 3H, J = 7.2 Hz, −O−(CH2)10−CH3), 1.29−1.47 (m, 16H, −O−CH2−CH2−(CH2)8− CH3), 1.78 (qn, 2H, J = 8.0 Hz, −O−CH2−CH2−C9H19), 2.17 (s, 3H, N-Ar-4- CH3), 2.22 (s, 3H, N-Ar-3-CH3), 3.11 (dd, 1H, J = 7.8, 17.1 Hz, Ha), 3.80 (dd, 1H, J = 12.3, 17.1 Hz, Hb), 3.93 (t, 2H, J = 6.6 Hz, −O−CH2−), 5.20 (dd, 1H, J = 7.5, 12.3 Hz, Hx), 6.71 (d, 1H, J = 8.1 Hz, N-ArHh), 6.86 (d, 2H, J = 8.7 Hz, ArHc=c’), 6.93 (d, 1H, J = 8.1 Hz, N-ArHi), 7.06 (s, 1H, N-ArHj), 7.25 (d, 2H, J = 8.7 Hz, ArHd=d’), 7.32-7.45 (m, 3H, ArHf=f’, g), 7.74(d, 2H, J = 7.8 Hz, ArHe=e’); 13C- NMR (75 MHz, CDCl3) δ 14.1, 18.8, 20.2, 22.7, 26.0, 29.3, 29.3, 29.4, 29.6, 29.7, 31.9, 43.6, 64.3, 67.9, 110.7, 114.3, 114.9 (2C), 115.1, 125.6 (2C), 127.0 (2C), 127.1, 128.3, 128.5, (2C), 129.8, 132.9, 134.7, 137.0, 143.1, 146.1, 158.4; EIMS: m/z 496 (M+, base peak). Anal. Calcd. For C34H44N2O (Mol. Wt. 496): C, 82.21; H, 8.93; N, 5.64; Found: C, 82.17; H, 8.89; N, 5.71%.
1-(3,4-Dimethylphenyl)-3-phenyl-5-(4-dodecyloxyphenyl)-2-pyrazoline(12h). 3-(4-Dodecyloxyphenyl)-1-phenylprop-2-en-1-one (3.90 g, 10 mmol) and (3,4-dimethylphenyl) hydrazaine (2.72 g, 20 mmol) were reacted according to the general procedure. Color pale yellow solid; yield 84% (3.27 g); m.p. 86–88 °C; Rf = 0.87 (petroleum ether-ethyl acetate, 4:1), FT-IR (KBr, cm−1): 1684, 1293, 1493, 1253, 1052, 1H-NMR (300 MHz, CDCl3) δ 0.90 (t, 3H, J = 7.2 Hz, −O−(CH2)11−CH3), 1.29−1.47 (m, 18H, −O−CH2−CH2−(CH2)9− CH3), 1.78 (qn, 2H, J = 7.8 Hz, −O−CH2−CH2−C10H21), 2.17 (s, 3H, N-Ar-4-CH3), 2.22 (s, 3H, N-Ar-3-CH3), 3.11 (dd, 1H, J = 7.5, 16.8 Hz, Ha), 3.80 (dd, 1H, J = 12.3, 17.1 Hz, Hb), 3.93 (t, 2H, J = 6.6 Hz, –O–CH2–), 5.20 (dd, 1H, J = 7.8, 12.3 Hz, Hx), 6.72 (d, 1H, J = 8.1 Hz, N-ArHh), 6.87 (d, 2H, J = 8.7 Hz, ArHc=c’), 6.93 (d, 1H, J = 8.1 Hz, N-ArHi), 7.06 (s, 1H, N- ArHj), 7.25 (d, 2H, J = 8.7 Hz, ArHd=d’), 7.32-7.43 (m, 3H, ArHf=f’, g), 7.74(d, 2H, J = 8.4 Hz, ArHe=e’); 13C-NMR (75 MHz, CDCl3) δ 14.1, 18.8, 20.2, 26.0, 29.3, 29.3, 29.4, 29.6, 29.6, 29.6, 29.6, 31.9, 43.6, 64.3, 68.0, 110.7, 114.9 (2C), 115.1, 125.6 (2C), 127.0 (2C), 127.1, 128.3, 128.5 (2C), 129.8, 133.0, 134.7, 137.0, 143.1, 146.1, 158.4; EIMS: m/z 510 (M+, base peak). Anal. Calcd. For C35H46N2O (Mol. Wt. 510): C, 82.30; H, 9.08; N, 5.48; Found: C, 82.24; H, 9.01; N, 5.54%.