A one-pot, four-component synthesis of N-substituted 2,4-diarylimidazoles

Synlett

Volumn , Issue 20, 2009, Pages 3263-3266

  Adib, Mehdi ^a   Ansari, Samira ^a   Feizi, Shahzad ^a   Damavandi, Jafar Asgarian ^b   Mirzaei, Peiman ^c  

^a UNIVERSITY OF TEHRAN   (Iran)

^b Teacher Training University   (Iran)

^c SHAHID BEHESHTI UNIVERSITY   (Iran)

Author keywords

1,2,4 trisubstituted 1 H imidazoles; Aldehydes; Cyclizations; Four component reactions; Heterocycles; Primary amines

Indexed keywords

2,4 DIARYLIMIDAZOLE; ALDEHYDE; AMINE; AMMONIUM ACETATE; IMIDAZOLE DERIVATIVE; KETONE DERIVATIVE; PHENACYL BROMIDE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL BOND; CHEMICAL STRUCTURE; HEATING; INFRARED SPECTROSCOPY; ONE POT SYNTHESIS;

EID: 72249095846     PISSN: 09365214     EISSN: 14372096     Source Type: Journal    
DOI: 10.1055/s-0029-1218381     Document Type: Article

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38. 1-Benzyl-2-(4-nitrophenyl)-4-phenyl-1H-imidazole (4b); Typical Procedure A mixture of 4-nitrobenzaldehyde (0.302 g, 2 mmol), benzylamine (0.214 g, 2 mmol), 2-bromo-1-phenylethanone (0.398 g, 2 mmol), and ammonium acetate (0.231 g, 3 mmol) was stirred at 130 °C for 2 h, then the reaction mixture was cooled to r.t. and the product precipitated from a 1:1 mixture of acetone-H2O and then recrystallized from n-hexane EtOAc (1:1) as colorless crystals. Yield: 0.67 g (95%); mp 178 °C. IR (KBr): 1594, 1513, 1502, 1489, 1477, 1446, 1414, 1357, 1330, 1289, 1200, 1176, 1103, 1026, 940, 854, 761, 731, 710 cm-1. 1H NMR (500.1 MHz, DMSO-d6): d = 5.48 (s, 2 H, CH2), 7.10 (d, J = 7.3 Hz, 2 H, 2 CH), 7.24 (t, J = 7.6 Hz, 1 H, CH), 7.26 (t, J = 7.5 Hz, 1 H, CH), 7.32 (dd, J = 7.2, 7.7 Hz, 1 H, CH), 7.38 (dd, J = 7.6, 7.8 Hz, 1 H, CH), 7.84 (d, J = 7.3 Hz, 2 H, 2 CH), 7.95 (d, J = 8.8 Hz, 2 H, 2 CH), 7.97 (s, CH, 1 H, CH), 8.28 (d, J = 8.8 Hz, 2 H, 2 CH). 13C NMR (75.5 MHz, DMSO-d6): d = 50.83 (CH2), 121.23, 124.29, 124.90, 127.05, 127.29, 128.21, 129.08, 129.33 and 129.53 (9 CH), 134.18, 136.89, 137.40, 141.23, 145.30 and 147.41 (6 °C). MS: m/z (%) = 355 (87) [M+], 116 (12), 92 (80), 90 (20), 89 (60), 77 (20), 65 (100). Anal. Calcd for C22H17N3O2 (355.40): C, 74.35; H, 4.82; N, 11.82. Found: C, 74.3; H, 4.8; N, 11.7. 1,2,4-Triphenyl-1H-imidazole (4a) Colorless crystals; mp 88-89 °C (lit.18 92-94 °C). IR (KBr): 1598, 1496, 1361, 1333, 1205, 1101, 1048, 784, 693 cm-1. 1H NMR (300.1 MHz, CDCl3): d = 7.26×7.33 (m, 6 H, 6 CH), 7.39×7.52 (m, 8 H, 8 CH), 7.93 (d, J = 7.8 Hz, 2 H, 2 CH). 13C NMR (75.5 MHz, CDCl3): d = 118.56, 125.06, 125.86, 127.03, 128.21, 128.24, 128.47, 128.64, 128.84 and 129.51 (10 CH), 130.32, 133.87, 138.49, 41.71 and 147.0 (5 °C). Anal. Calcd for C21H16N2 (296.37): C, 85.11; H, 5.44; N, 9.45. Found: C, 85.0; H, 5.5; N, 9.4. MS: m/z (%) = 296 (7) [M+], 279 (6), 225 (8), 197 (20), 180 (6), 167 (11), 149 (28), 105 (100), 77 (52), 51 (12). 1-Benzyl-2-(3-nitrophenyl)-4- phenyl-1H-imidazole (4c) Colorless crystals; mp 183×185 °C. IR (KBr): 1605, 1549, 1488, 1463, 1434, 1374, 1345, 1304, 1240, 1207, 1152, 1099, 939, 855, 818, 766, 667 cm-1. 1H NMR (300.1 MHz, DMSO-d6): d = 5.44 (s, 2 H, CH2), 7.12 (d, J = 7.3 Hz, 2 H, 2 CH), 7.21×7.43 (m, 6 H, 6 CH), 7.73 (dt, J = 1.4, 8.0 Hz, 1 H, CH), 7.84 (d, J = 7.7 Hz, 2 H, 2 CH), 7.95 (s, 1 H, CH), 8.09 (d, J = 7.6 Hz, 1 H, CH), 8.24 (d, J = 8.2 Hz, 1 H, CH), 8.38 (d, J = 1.4 Hz, 1 H, CH). 13C NMR (75.5 MHz, DMSO-d6): d = 50.92 (CH2), 120.27, 123.17, 123.49, 125.06, 127.11, 127.18, 128.18, 128.92, 129.23 and 130.58 (10 CH), 132.57 and 134.49 (2 °C), 134.71 (CH), 137.33, 141.15, 145.39 and 148.62 (4 °C). MS: m/z (%) = 355 (5) [M+], 155 (3), 111 (12), 91 (100), 80 (38), 71 (59), 57 (82). Anal. Calcd for C22H17N3O2 (355.40): C, 74.35; H, 4.82; N, 11.82. Found: C, 74.2; H, 4.9; N, 11.6. 2-(4-Nitrophenyl)-4-phenyl-1-propyl-1H-imidazole (4e) Colorless crystals; mp 104 °C. IR (KBr): 1595, 1510, 1475, 1384, 1329, 1203, 1100, 1017, 946, 913, 847, 804, 759, 691 cm-1. 1H NMR (300.1 MHz, CDCl3): d = 0.95 (t, J = 7.4 Hz, 3 H, CH3), 1.85 (sext, J = 7.3 Hz, 2 H, CH2CH3), 4.06 (t, J = 7.2 Hz, 2 H, NCH2), 7.29 (t, J = 7.0 Hz, 1 H, CH), 7.40 (s, 1 H, CH), 7.41 (dd, J = 7.0, 7.5 Hz, 2 H, 2 CH), 7.84 (d, J = 7.5 Hz, 2 H, 2 CH), 7.88 (d, J = 8.6 Hz, 2 H, 2 CH), 8.35 (d, J = 8.6 Hz, 2 H, 2 CH). 13C NMR (75.5 MHz, CDCl3): d = 11.12 (CH3), 24.47 and 49.04 (2 CH2), 117.72, 123.93, 124.92, 127.16, 128.67 and 129.50 (6 CH(, 133.64, 137.08, 142.18, 145.49 and 147.60 (5 C). MS: m/z (%) = 307 (24) [M+], 279 (20), 167 (42), 151 (13), 149 (100), 113 (10), 105 (12), 83 (10), 77 (9), 71 (18), 57 (31), 55 (17), 43 (26). Anal. Calcd for C18H17N3O2 (307.35): C, 70.34; H, 5.58; N, 13.67. Found: C, 70.3; H, 5.6; N, 13.6. 2-(4-Nitrophenyl)-1,4-diphenyl-1H-imidazole (4h) Colorless crystals; mp 154 °C. IR (KBr): 1593, 1506, 1418, 1387, 1331, 1200, 1166, 1102, 1073, 974, 913, 849, 745, 692 cm-1. 1H NMR (300.1 MHz, CDCl3): d = 7.28×7.35 (m, 3 H, 3 CH), 7.45 (dd, J = 7.4, 8.0 Hz, 2 H, 2 CH), 7.50 (s, 1 H, CH), 7.51×7.53 (m, 3 H, 3 CH), 7.66 (d, J = 8.6 Hz, 2 H, 2 CH), 7.91 (d, J = 7.8 Hz, 2 H, 2 CH), 8.13 (d, J = 8.5 Hz, 2 H, 2 CH). 13C NMR (75.5 MHz, CDCl3): d = 120.13, 123.54, 125.10, 125.94, 127.50, 128.77, 129.04, 129.08 and 129.98 (9 CH), 133.27, 136.26, 137.95, 142.70, 144.37 and 147.22 (6 C). MS: m/z (%) = 341 (6) [M+], 279 (20), 167 (43), 149 (100), 113 (10), 105 (9), 83 (10), 71 (19), 57 (31). Anal. Calcd for C21H15N3O2 (341.37): C, 73.89; H, 4.43; N, 12.31. Found: C, 73.8; H, 4.5; N, 12.2. 2-(4-Chlorophenyl)-1,4-diphenyl-1H-imidazole (4i) Colorless crystals; mp 146×148 °C. IR (KBr): 1596, 1489, 1447, 1413, 1240, 1206, 1170, 1087, 1013, 975, 912, 830, 751, 691 cm-1. 1H NMR (300.1 MHz, CDCl3): d = 7.24×7.3
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