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13. General procedure for the synthesis of 2,4,5-trisubstituted imidazoles:
In a 50 ml round-bottom flask, 1,2-diketone (1 mmol), aldehyde
(1 mmol) and ammonium acetate (2 mmol) were stirred in the
presence of 10 mol % of InCl3Á3H2O in methanol (2 ml) at room
temperature for the stipulated time (Table 2). The progress of the
reaction was monitored by TLC. After the completion of the reaction,
the reaction mixture was diluted with water (3 ml) and extracted with
ethyl acetate (2 Â 15 ml). The organic layer was dried over Na2SO4,
concentrated and recrystallized from ethanol to afford pure
product.
4. For reviews, see: (a) Dupont, J.; de Souza, R. F.; Suarez, P. A. Z.
Chem. Rev. 2002, 102, 3667; (b) Nara, S. J.; Naik, P. U.; Harjani, J.
R.; Salunkhe, M. M. Indian J. Chem. 2001, 45B, 2257; (c) Chowd-
hury, S.; Mohan, R. S.; Scott, J. L. Tetrahedron 2007, 63, 2363.
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592.
2-(3,4-Dimethoxyphenyl)-4,5-diphenyl-1H-imidazole (1j): Mp 215 °C;
1H NMR (DMSO-d6, 300 MHz): d 3.85 (s, 3H), 3.89 (s, 3H), 7.21–
7.81 (m, 13H), 12.52 (br s, 1H); FT-IR (KBr, cmÀ1): 1545, 1633, 3446;
ESI-MS (m/z): 357 (M++1). Anal. Calcd for C23H20N2O2: C, 77.51;
H, 5.66; N, 7.86. Found: C, 77.57; H, 5.62; N, 7.89.
2-(1-Phenylethyl)-4,5-diphenyl-1H-imidazole (1r): Mp 185–187 °C; 1H
NMR (DMSO-d6, 300 MHz): d 1.17 (d, J = 7.2 Hz, 3H), 4.31 (q,
J = 7.2 Hz, 1H), 7.14–7.79 (m, 15H), 12.44 (br s, 1H); FT-IR (KBr,
cmÀ1): 1526, 1631, 3431; ESI-MS (m/z): 325 (M++1). Anal. Calcd for
6. (a) Usyatinsky, A. Y.; Khemelnitsky, Y. L. Tetrahedron Lett. 2000,
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Hall, R. F.; Garigipati, R. S.; Bender, P. E.; Erhard, K. F.; Krog, A.
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Claremon, D. A.; Libby, B. E.; Nguyen, K. T.; Pitzenberger, S. M.;
Selnick, H. G.; Smith, G. R.; Tebben, A.; Vacca, J. P.; Varga, S. L.;
Agarwal, L.; Dancheck, K.; Forsyth, A. J.; Fletcher, D. S.; Frantz, B.;
Hanlon, W. A.; Harper, C. F.; Hofsess, S. J.; Kostura, M.; Lin, J.;
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1999, 42, 2180.
C
23H20N2: C, 85.15; H, 6.21; N, 8.63. Found: C, 85.19; H, 6.27; N,
8.69.
14. General procedure for the synthesis of 1,2,4,5-tetrasubstituted imid-
azoles:
In a 50 ml round-bottom flask, 1,2-diketone (1 mmol), aldehyde
(1 mmol), primary amine (1 mmol) and ammonium acetate (1 mmol)
were stirred in the presence of 10 mol % of InCl3Á3H2O in methanol
(2 ml) at room temperature for the stipulated time (Table 3). The
reaction was monitored by TLC. After completion of the reaction, the
reaction mixture was diluted with water (5 ml) and extracted with
ethyl acetate (2 Â 25 ml). The organic layer was dried over Na2SO4
and concentrated. The products were separated and purified by
column chromatography on silica gel (60–120 mesh) using ethyl
acetate/hexane mixture as an eluent to afford pure tetrasubstituted
imidazoles.
1-Methyl-2,4,5-triphenylimidazole (2b):8a Mp 144–145 °C; 1H NMR
(CDCl3, 300 MHz): d 3.51 (s, 3H), 7.16–7.76 (m, 15H); FT-IR
(CHCl3, cmÀ1): 1602, 1581; ESI-MS (m/z): 311 (M++1). Anal. Calcd
for C22H18N2: C, 85.13; H, 5.85; N, 9.03. Found: C, 85.18; H, 5.89; N,
9.02.