A. A. Marzouk, S. K. Mohamed, E. T. Aljohani, and A. A. Abdelhamid
Vol 000
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1578 (C¼C), 1442, 1212, 1173, 1025, 828, 725, 695, 537;
1H NMR (DMSO-d6, 400 MHz): 3.824 (s, 3H, CH3O),
4.48 (d, 2H, CH2N), 4.744 (d, 1H, ¼CH2), 5.093 (d, 1H,
¼CH2), 5.78 (p, 1H, CH¼CH2), 6.922–7.682 (m, 14H,
Ar–H); 13C NMR (400 MHz, DMSO-d6): 46.638,
55.208, 110.178, 113.817, 114.212, 114.590, 116.352,
117.612, 120.740, 126.075, 126.520, 127.804, 128.059,
128.248, 128.660, 129.804, 130.941, 131.064, 131.624,
134.234, 134.546, 135.115, 137.057, 146.500,
159.187 ppm. Anal. Calcd for C25H22N2O: C, 81.94; H,
1062, 876, 729, 703; H NMR (DMSO-d6, 400 MHz):
3.83 (s, 3H, CH3O), 3.90 (s, 3H, CH3O), 4.25 (d, 2H,
CH2N), 4.54 (d, 1H, ¼CH2), 4.88 (d, 1H, ¼CH2), 5.55
(p, 1H, CH¼CH2), 6.50–7.48 (m, 13H, Ar–H); 13C NMR
(400 MHz, DMSO-d6): 46.157, 54.967, 55.281, 55.396,
55.796, 98.292, 105.128, 112.298, 115.778, 125.847,
126.648, 127.906, 128.221, 128.860, 144.639, 157.873,
158.093, 159.447, 161.516, 164.681 ppm. DEPT (ppm):
46.022 (CH2) and 115.624 (CH2) disappeared. Anal.
Calcd for C26H24N2O2: C, 78.76; H, 6.10; N, 7.07.
6.05; N, 7.64. Found: C, 81.70; H, 6.15; N, 7.40.
Found: C, 78.39; H, 6.30; N, 7.27.
(1N-Allyl-4,5-diphenyl-1H-imidazol-2-yl)benzoate (8h).
2-(4-Methoxyphenyl)-1N-pentyl-4,5-diphenyl-1H-imidazole
(8l).
Mp 109–111°C. FTIR (KBr, cmꢀ1): 3059 (C–H
Mp 224–227°C FTIR (KBr, cmꢀ1): 3083 (C–H
aromatic), 2990, 2965, 2845 (C–H aliphatic), 1708
(C¼O), 1612 (C¼N), 1504 (C¼C), 1443, 1270, 1161,
aromatic), 2954, 2907, 2836 (C–H aliphatic), 1630 (¼C–
H), 1610 (C¼N), 1539, 1467 (C¼C), 1261, 1180, 1077,
1
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824, 713, 692; H NMR (DMSO-d6, 400 MHz): 0.601
1072, 861, 720, 696; H NMR (DMSO-d6, 300 MHz):
(tr, 3H, CH3), 0.899 (m, 4H, 2CH2), 1.261 (p, 2H, CH2),
3.858 (s, 3H, OCH3), 3.858 (tr, 2H, CH2N), 7.103–7.630
(m, J = 8.8 Hz, 2.0 Hz, 14H, Ar–H); 13C NMR
(400 MHz, DMSO-d6): 13.950, 21.559, 28.214, 29.597,
44.614, 55.760, 114.559, 124.120, 126.544, 128.547,
129.319, 129.653, 130.415, 130.644, 131,369, 134.648,
136.434, 147.158, 160.049 ppm. Anal. Calcd for
C27H28N2O: C, 81.78; H, 7.12; N, 7.06. Found: C, 81.64;
3.55 (d, 1H, ¼CH2), 4.80 (m, 5H, CH2N, CH2O, and
¼CH2), 5.076 (p, 1H, CH¼CH2), 5.30 (d, 1H, ¼CH2),
5.44 (d, 1H, ¼CH2), 6.06 (p, 1H, CH¼CH2), 7. 210–
8.444 (m, 14H, Ar–H); 13C NMR (400 MHz, DMSO-d6):
65.400, 90.238, 118.213, 119.415, 126.017, 128.191,
128.965, 129.105, 129.722, 130.175, 130.652, 131.854,
132.488, 132.711, 135.501, 136.671, 164,925, 169.741,
196.637 ppm. Anal. Calcd for C28H24N2O2: C, 79.98; H,
H, 6.85; N, 7.42.
5.75; N, 6.66. Found: C, 79.65; H, 6.05; N, 6.99.
2-(3,4-Dimethoxyphenyl)-1N-pentyl-4,5-diphenyl-1H-
1N-Allyl-2-(4-chlorophenyl)-4,5-diphenyl-1H-imidazole
imidazole (8m). Mp 151-153°C. FTIR (KBr, cmꢀ1): 3050
(8i).
Mp 108–110°C. FTIR (KBr, cmꢀ1): 3055 (C–H
(C–H aromatic), 2997, 2956, 2932, 2859, 2838 (C–H
aliphatic), 1603 (C¼N), 1502, 1439 (C¼C), 1254, 1175,
1073, 803, 728, 705, 530; 1H NMR (DMSO-d6,
400 MHz): 0.59 (tr, 3H, CH3), 0.90 (m, 4H, 2CH2),
1.250 (p, 2H, CH2), 3.850 (s, 6H, 2CH3O), 3.870 (tr, 2H,
CH2N), 7.10–7.730 (m, 13H, Ar–H); 13C NMR
(400 MHz, DMSO-d6): 13.592, 21.248, 27.933, 29.341,
44.333, 55.727, 55.768, 109.000, 111.783, 112.615,
118.073, 121.382, 123.408, 126.157, 126.577, 127.886,
128.174, 128.965, 129.278, 129.566, 131.402, 134.966,
136.366, 145.850, 146.912, 148.970, 149.225,
149.423 ppm; mass spectrum: 428 (M+2), 427 (M+1).
Anal. Calcd for C28H30N2O2: C, 78.84; H, 7.09; N, 6.57.
aromatic), 2996, 2956, 2932 (C–H aliphatic), 1602
(C¼N), 1516 (C¼C), 1448, 1273, 1124, 1012, 829, 732,
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695, 574; H NMR (DMSO-d6, 400 MHz): 4.48 (tr, 2H,
CH2N), 4.72 (d, 1H, CH¼CH2), 5.06 (d, 1H, CH¼CH2),
5.76 (p, 1H, CH¼CH2), 7.10–7.90 (m, J = 8.3 Hz,
4.4 Hz, 14H, Ar–H); 13C NMR (400 MHz, DMSO-d6):
46.613, 116.418, 126.034, 126.240, 128.051, 128.644,
128.973, 129.022, 129.533, 130.101, 130.340, 130.504,
130.883, 133.534, 134.003, 134.390, 136.769,
145.471 ppm. Anal. Calcd for C24H19ClN2: C, 77.72; H,
5.16; N, 7.55. Found: C, 77.85; H, 5.36; N, 7.50.
1N-Allyl-2-(4-bromophenyl)-4,5-diphenyl-1H-imidazole
(8j).
Mp 124–126°C. FTIR (KBr, cmꢀ1): 3067 (C–H
aromatic), 2991, 2924, 2822 (C–H aliphatic), 1601
(C¼N), 1563 (C¼C), 1445, 1270, 1123, 1072, 834, 735,
Found: C, 78.49; H, 7.39; N, 6.72.
2-(2,6-Dichlorophenyl)-1N-pentyl-4,5-diphenyl-1H-
imidazole (8n). Mp 120–123°C. FTIR (KBr, cmꢀ1): 3053
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696, 548; H NMR (DMSO-d6, 400 MHz): 4.50 (t, 2H,
(C–H aromatic), 2954, 2929, 2856 (C–H aliphatic), 1602
(C¼N), 1501, 1443 (C¼C), 1231, 1155, 1072, 845, 737,
CH2N), 4.71 (d, 1H, CH¼CH2), 5.07 (d, 1H, CH¼CH2),
5.76 (p, 1H, CH¼CH2), 7.11–7.70 (m, 14H, Ar–H); 13C
NMR (400 MHz, DMSO-d6): 46.621, 116.435, 122.230,
126.042, 126.256, 128.067, 128.981, 129.039, 129.879,
130.348, 130.389, 130.496, 130.883, 131.566, 134.003,
134.382, 136.819, 145.529 ppm. Anal. Calcd for
C24H19BrN2: C, 69.41; H, 4.61; N, 6.74. Found: C,
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694, 549; H NMR (DMSO-d6, 400 MHz): 0.58 (tr, 3H,
CH3), 0.88 (m, 4H, 2CH2), 1.240 (p, 2H, CH2), 3.530 (tr,
2H, CH2N), 7.10–7.80 (m, 13H, Ar–H); 13C NMR
(400 MHz, DMSO-d6): 13.493, 21.215, 27.818, 29.119,
43.995, 126.067, 126.371, 128.248, 128.792, 129.096,
129.212, 129.459, 129.730, 130.825, 130.990, 132.719,
134.612, 136.193, 136.794, 141.289 ppm; mass
spectrum: 437 (M+2), 435 (M+). Anal. Calcd for
C26H24Cl2N2: C, 71.72; H, 5.56; N, 6.43. Found: C,
82.49; H, 6.45; N, 6.76.
69.31; H, 4.72; N, 6.88.
1N-Allyl-2-(2,4-dimethoxyphenyl)-4,5-diphenyl-1H-
imidazole (8k). Mp 200–202°C. FTIR (KBr, cmꢀ1): 3048
(C–H aromatic), 2990, 2955, 2929, 2835 (C–H aliphatic),
1602 (C¼N), 1583, 1525 (C¼C), 1460, 1244, 1144,
Journal of Heterocyclic Chemistry
DOI 10.1002/jhet