GREEN SYNTHESIS OF 2,4,5-TRIARYLIMIDAZOLES
1139
J ¼ 8.00 Hz), 7.44 (d, 2H, J ¼ 8.00 Hz), 7.38 (d, 2H, J ¼ 8.00 Hz), 7.29 (d, 2H,
J ¼ 8.00 Hz), 7.24 (d, 2H, J ¼ 8.00 Hz), 7.11 (d, 2H, J ¼ 7.60 Hz), 2.35 (s, 6H,
CH3), 2.23 (s, 3H, CH3); 13C NMR (100 MHz, DMSO-d6) d: 145.8, 138.0, 137.4,
137.2, 136.0, 129.7, 129.6, 129.1, 128.8, 128.6, 128.3, 128.0, 127.5, 125.6. MS m=z
(%): (M þ H)þ ¼ 339.6 (100). Anal. calcd. for C24H22N2: C, 85.17; H, 6.55; N,
8.28. Found: C, 84.84; H, 6.57; N, 8.19.
Compound 3j. Mp 263–264 ꢀC. IR (KBr): 3423, 3023, 1517, 1491, 1434, 1089,
1
820, 729 cmꢁ1. H NMR (400 MHz, DMSO-d6) d: 12.67 (s, 1H, NH), 8.09 (d, 2H,
J ¼ 8.80 Hz), 7.54 (d, 2H, J ¼ 8.40 Hz), 7.44 (d, 2H, J ¼ 8.00 Hz), 7.39 (d, 2H,
J ¼ 8.00 Hz), 7.25 (d, 2H, J ¼ 8.00 Hz), 7.11 (d, 2H, J ¼ 8.00 Hz), 2.35 (s, 3H,
CH3), 2.30 (s, 3H, CH3); 13C NMR (100 MHz, DMSO-d6) d: 144.6, 137.6, 137.5,
136.1, 133.1, 132.8, 129.8, 129.6, 129.2, 129.1, 128.7, 128.6, 127.5, 127.3. MS m=z
(%): (M þ H)þ ¼ 359.6 (100). Anal. calcd. for C23H19ClN2: C, 76.98; H, 5.34; N,
7.81. Found: C, 76.69; H, 5.36; N, 7.73.
Compound 3k. Mp 290–291 ꢀC. IR (KBr): 3439, 3057, 1407, 1093, 833,
729 cmꢁ1 1H NMR (400 MHz, DMSO-d6) d: 12.79 (s, 1H, NH), 8.07 (d, 2H,
.
J ¼ 7.20 Hz), 7.56–7.38 (m, 11H); 13C NMR (100 MHz, DMSO-d6) d: 146.5, 136.9,
134.3, 133.0, 131.7, 130.6, 130.5, 130.1, 129.3, 129.2, 128.9, 128.8, 127.8, 125.8.
MS m=z (%): (M)þ ¼ 365.6 (100). Anal. calcd. for C21H14Cl2N2: C, 69.05; H, 3.86;
N, 7.67. Found: C, 68.79; H, 3.88; N, 7.59.
Compound 3l. Mp 274–276 ꢀC. IR (KBr): 3425, 3078, 2891, 1479, 1237, 1091,
1
1039, 833, 740 cmꢁ1. H NMR (400 MHz, CDCl3) d: 7.45 (d, 4H, J ¼ 7.20 Hz), 7.42
(s, 1H), 7.35–7.32 (m, 5H), 6.88 (d, 1H, J ¼ 8.00 Hz), 6.04 (s, 2H, CH2); 13C NMR
(100 MHz, DMSO-d6) d: 148.1, 146.4, 136.6, 134.3, 132.9, 131.6, 130.5, 130.1,
129.3, 129.2, 128.8, 127.4, 124.9, 120.0, 109.0, 106.1, 101.8. MS m=z (%):
(M)þ ¼ 409.5 (100). Anal. calcd. for C22H14Cl2N2O2: C, 64.56; H, 3.45; N, 6.84.
Found: C, 64.30; H, 3.46; N, 6.77.
Compound 3m. Mp 258–259 ꢀC IR (KBr): 3427, 3068, 2961, 1614, 1496,
1441, 1248, 830, 742 cmꢁ1. 1H NMR (400 MHz, CDCl3) d: 7.86 (d, 2H, J ¼ 8.40 Hz),
7.46 (d, 4H, J ¼ 8.00 Hz), 7.32 (d, 4H, J ¼ 8.00 Hz), 6.99 (d, 2H, J ¼ 8.80 Hz), 3.88 (s,
3H, OCH3); 13C NMR (100 MHz, DMSO-d6) d: 160.1, 146.6, 136.5, 136.5, 134.4,
132.8, 131.6, 130.5, 130.2, 129.2, 129.2, 128.8, 127.7, 127.3, 123.3, 114.6. MS m=z
(%): (M)þ ¼ 395.6 (100). Anal. calcd. for C22H16Cl2N2O: C, 66.85; H, 4.08; N,
7.09. Found: C, 66.59; H, 4.10; N, 7.02.
Compound 3n. Mp 271–272 ꢀC. IR (KBr): 3438, 3073, 1654, 1479, 1434,
1
1090, 831, 731 cmꢁ1. H NMR (400 MHz, DMSO-d6) d: 12.86 (s, 1H, NH), 8.09
(d, 2H, J ¼ 8.40 Hz), 7.69 (d, 2H, J ¼ 8.40 Hz), 7.64–7.51 (m, 6H), 7.37 (d, 2H,
J ¼ 6.40 Hz);13C NMR (100 MHz, DMSO-d6) d: 145.4, 137.0.5, 134.1, 133.5, 133.1,
131.8, 130.6, 129.9, 129.4, 129.2, 129.3, 128.9, 128.1, 127.4. MS m=z (%):
(M þ H)þ ¼ 399.7 (100). Anal. calcd. for C21H13Cl3N2: C, 63.10; H, 3.28; N, 7.01.
Found: C, 62.86; H, 3.30; N, 6.94.