2
320
G. Bratulescu
SHORT PAPER
Table 1 4,5-Disubstituted 1H-Imidazole Derivatives
1
2
1
Prod. R
R
Time Temp Yield Anal. Calcd/Found
IR
H NMR
Mp
–1
(
min) (°C) (%) C (%) H (%) N (%) (cm )
(d)
(°C)
1
2
3
4
5
H
H
3.5 106 78
52.94/ 5.88/ 41.17/ 3124 (s, NH), 2916 (s), 7.12 (s, 2 H, H3,4), 7.72 (s, 1 H,
2.93 5.85 41.16 1451 (s), 1066 (vs), 660 H2), 10.52 (br s, 1 H, NH)
vs)
90.5
2
2
5
(Lit.
88–91)
56
(
H
Me
Me
Et
4
3
4
103 76
101 72
105 75
58.53/ 7.31/ 34.14/ 3117 (s, NH), 2920 (vs), 2.24 (s, 3 H, 4-CH ), 6.73 (s, 1 H,
3
5
8.51 7.67 34.13 1449 (s), 1126 (s), 663 H5), 7.50 (s, 1 H, H2), 10.92 (br
m) s, 1 H, NH)
(
Me
H
62.50/ 8.33/ 29.16/ 3110 (s, NH), 2931 (vs), 2.25 (s, 3 H, 4-CH ), 2.33 (s, 3 H,
3
63
76
97
6
2.48 8.30 29.15 1438 (s), 1132 (m), 677 5-CH ), 7.43 (s, 1 H, H2), 10.67
3
(
m)
(br s, 1 H, NH)
62.50/ 8.33/ 29.16/ 3121 (s, NH), 2924 (vs), 1.29 (t, 3 H, CH ), 2.65 (q, 2 H,
3
6
2.47 8.32 29.13 1428 (s), 1129 (s), 657 CH ), 6.97 (s, 1 H, H5), 7.48 (s, 1
2
(
m)
H, H2), 10.79 (br s, 1 H, NH)
Et
Et
3.5 102 71
67.74/ 9.67/ 22.58/ 3105 (s, NH), 2915 (vs), 1.28 (t, 3 H, CH ), 1.24 (t, 3 H,
3
6
7.71 9.63 22.55 1435 (s), 1113 (s), 649 CH ), 2.61 (q, 2 H, CH ), 2.54 (q,
3 2
(
m)
2 H, CH ), 7.09 (s, 1 H, H2),
2
1
1.12 (br s, 1 H, NH)
6
H
Ph
Ph
4
108 79
75.00/ 5.55/ 19.44/ 3025 (s, NH), 2850 (m), 7.24 (m, 1 H, Hp-Ph), 7.34 (s, 1
4.98 5.52 19.43 1490 (m), 1076 (m), 758 H, H5), 7.38 (m, 2 H, Hm,m¢-Ph),
130
230
7
(
vs)
7.71 (s, 1 H, H2), 7.72 (m, 2 H,
Ho,o¢-Ph), 11.06 (br s, 1 H, NH)
7
8
Ph
3.5 112 81
81.81/ 5.45/ 12.72/ 3061 (s, NH), 2990 (s), 7.26–7.34 (m, 6 H, Hm,p-2Ph),
8
1.80 5.43 12.71 1502s, 958 (vs), 768
vs)
7.48 (m, 4 H, Ho-2Ph), 7.81 (s, 1
H, H2), 12.58 (br s, 1 H, NH)
(
4-ClC H4 4-ClC H 4
4
117 83
62.28/ 3.46/
6
9.68/ 3078 (s, NH), 2995 (s), 7.27 (m, 4 H, Hm-2Ph), 7.41 (m, 254
9.67 1511 (s), 964 (s), 759
m)
6
6
2.25 3.45
4 H, Ho-2Ph), 7.68 (s, 1 H, H2),
12.75 (br s, 1 H, NH)
(
(
7) Wiebe, L.; Mcewan, A. J. B.; Kumar, P. (The Governors of
the University of Alberta, Canada) WO 102759, 2006;
Chem. Abstr. 2006, 145, 377533.
(15) Heras, M.; Ventura, M.; Linden, A.; Villalgordo, J. M.
Synthesis 1999, 9, 1613.
(16) Zimmer, H.; Benson, H. D. Chimia 1972, 26, 131.
(17) Ellinger, L. P.; Goldberg, A. A. J. Chem. Soc. 1949, 263.
(18) Wolkenberg, S. E.; Wisnoski, D. D.; Leister, W. H.; Wang,
Y.; Zhao, Z.; Lindsley, C. W. Org. Lett. 2004, 6, 1453.
(19) Bratulescu, G.; Le Bigot, Y.; Delmas, M. Synth. Commun.
2000, 30, 171.
(
(
8) Kumar, J. R.; Jat, J. L.; Pathak, D. P. E-J. Chem. 2006, 3,
278.
9) Ou, W.-H.; Huang, Z.-Z. Green Chem. 2006, 8, 731.
(
10) Mehdi, H.; Bodor, A.; Lantos, D.; Horvath, I. T.; De Vos, D.
E. J. Org. Chem. 2007, 72, 517.
(
(
11) Radziszewski, B. Chem. Ber. 1882, 15, 1493.
12) Glister, J. F.; Vaughan, K. J. Heterocycl. Chem. 2006, 43,
(20) Bratulescu, G. Rev. Roum. Chim. 2000, 45, 883.
(21) Bratulescu, G. Synthesis 2005, 2833.
2
17.
(22) Hiraoka, R.; Watanabe, H.; Senna, M. Tetrahedron Lett.
2006, 47, 3111.
(
(
13) Heim-Riether, A.; Healy, J. J. Org. Chem. 2005, 70, 7331.
14) Kawakami, J. I.; Kimura, K.; Yamaoka, M. Synthesis 2003,
677.
Synthesis 2009, No. 14, 2319–2320 © Thieme Stuttgart · New York