Rapid one-pot preparation of 2-substituted benzimidazoles from 2-nitroanilines using microwave conditions

Tetrahedron Letters

Volumn 46, Issue 39, 2005, Pages 6741-6743

  VanVliet, David S ^a,d   Gillespie, Paul ^b   Scicinski, Jan J ^a,c  

^a Nuada Pharmaceuticals Inc   (United States)

^b HOFFMANN LA ROCHE INC   (United States)

^c ALZA CORPORATION   (United States)

^d Nanosyn Inc   (United States)

Author keywords

Benzimidazole formation; Cyclization; Microwave

Indexed keywords

ANILINE DERIVATIVE; BENZIMIDAZOLE DERIVATIVE;

ACYLATION; ARTICLE; CYCLIZATION; DRUG SYNTHESIS; MICROWAVE RADIATION; REDUCTION;

EID: 24044521615     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2005.07.130     Document Type: Article

References (26)

1. P. Lindberg, P. Nordberg, T. Alminger, A. Brandstrom, and B. Wallmark J. Med. Chem. 29 1986 1327
2. R. Mannhold Drugs Future 10 1985 570
3. M.A. Pagano, M. Andrzejewska, M. Ruzzene, S. Sarno, L. Cesaro, J. Bain, M. Elliott, F. Meggio, Z. Kazimierczuk, and L.A. Pinna J. Med. Chem. 47 2004 6239
4. H. Ueno, S. Katoh, K. Yokota, J.-i. Hoshi, M. Hayashi, I. Uchida, K. Aisaka, Y. Hase, and H. Cho Bioorg. Med. Chem. Lett. 14 2004 4281
5. P.L. Beaulieu, Y. Bousquet, J. Gauthier, J. Gillard, M. Marquis, G. McKercher, C. Pellerin, S. Valois, and G. Kukolj J. Med. Chem. 47 2004 6884
6. R.M. Slade, M.A. Phillips, and J.G. Berger Mol. Diversity 4 1998 215
7. C.M. Sun Methods Mol. Biol. 201 2002 141
8. P.M. Bendale, and C.-M. Sun J. Comb. Chem. 4 2002 359
9. S.P. Andrews, D. Jonsson, B.H. Warrington, and M. Ladlow Comb. Chem. High Throughput Screen. 7 2004 163
10. Y.K. Yun, J.A. Porco Jr., and J. Labadie Synlett 2002 739
11. J.J. Clemens, M.D. Davis, K.R. Lynch, and T.L. Macdonald Bioorg. Med. Chem. Lett. 14 2004 4903
12. R. Rastogi, and S. Sharma Synthesis 1983 861
13. G.A. Morales, J.W. Corbett, and W.F. DeGrado J. Org. Chem. 63 1998 1172
14. G. Navarrete-Vazquez, R. Cedillo, A. Hernandez-Campos, L. Yepez, F. Hernandez-Luis, J. Valdez, R. Morales, R. Cortes, M. Hernandez, and R. Castillo Bioorg. Med. Chem. Lett. 11 2001 187
15. V.K. Tandon, and M. Kumar Tetrahedron Lett. 45 2004 4185
16. M.A. Weidner-Wells, K.A. Ohemeng, V.N. Nguyen, S. Fraga-Spano, M.J. Macielag, H.M. Werblood, B.D. Foleno, G.C. Webb, J.F. Barrett, and D.J. Hlasta Bioorg. Med. Chem. Lett. 11 2001 1545
17. M.A. Phillips J. Chem. Soc. 1928 2393
18. K. Bougrin, A. Loupy, A. Petit, B. Daou, and M. Soufiaoui Tetrahedron 57 2001 163
19. J.J. Vanden Eynde, A. Mayence, P. Lor, and Y. Vanhaverbeke Bull. Soc. Chim. Belg. 104 1995 387
20. A.K. Bose, M.S. Manhas, M. Ghosh, V.S. Raju, K. Tabei, and Z. Urbanczyk-Lipkowska Heterocycles 30 1990 471
21. W.B. Yeh, M.J. Lin, and C.M. Sun Comb. Chem. High Throughput Screen. 7 2004 251
22. H. Yu, H. Kawanishi, and H. Koshima Heterocycles 60 2003 1457
23. Unpublished Results.
24. CEM Corporation, PO Box 200, Matthews, NC 28106.
25. For reactions of 5-carboxy-2-nitroaniline, none of the dimeric derivative, potentially formed from participation of the carboxylic acid substituent, was detected:
26. NMR data for all the benzimidazoles can be found in Supplementary data.