Solvent-free chemoselective synthesis of some novel substituted 2-arylbenzimidazoles using amino acid-based prolinium nitrate ionic liquid as catalyst

Journal of Heterocyclic Chemistry

Volumn 46, Issue 1, 2009, Pages 74-78

  Rostamizadeh, Shahnaz ^a   Aryan, Reza ^a   Ghaieni, Hamid Reza ^a   Amani, Ali Mohammad ^a  

^a K N TOOSI UNIVERSITY OF TECHNOLOGY   (Iran)

Author keywords

[No Author keywords available]

Indexed keywords

2 (4 BROMOPHENYL) 5 NITROBENZIMIDAZOLE; 2 (4 BROMOPHENYL)BENZIMIDAZOLE; 2 (4 BROMOPHENYL)BENZIMIDAZOLE 5 CARBOXYLIC ACID; 2 (4 CHLOROPHENYL) 5 NITROBENZIMIDAZOLE; 2 (4 CHLOROPHENYL)BENZIMIDAZOLE; 2 (4 CHLOROPHENYL)BENZIMIDAZOLE 5 CARBOXYLIC ACID; 2 (4 CYANOPHENYL) 5 NITROBENZIMIDAZOLE; 2 (4 CYANOPHENYL)BENZIMIDAZOLE 5 CARBOXYLIC ACID; 2 (4 FLUOROPHENYL)BENZIMIDAZOLE; 2 (4 METHOXYPHENYL)BENZIMIDAZOLE; 2 (4 METHYLPHENYL) 5 NITROBENZIMIDAZOLE; 2 (4 METHYLPHENYL)BENZIMIDAZOLE; 2 (4 METHYLPHENYL)BENZIMIDAZOLE 5 CARBOXYLIC ACID; 2 (4 NITROPHENYL) 5 NITROPHENYLBENZIMIDAZOLE; 2 (4 NITROPHENYL)BENZIMIDAZOLE; 2 (4 NITROPHENYL)BENZIMIDAZOLE 5 CARBOXYLIC ACID; BENZIMIDAZOLE DERIVATIVE; IONIC LIQUID; PHENZIDOLE; PROLINIUM NITRATE; UNCLASSIFIED DRUG;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CATALYSIS; DRUG STRUCTURE; DRUG SYNTHESIS; PROTON NUCLEAR MAGNETIC RESONANCE; SUBSTITUTION REACTION;

EID: 61849105513     PISSN: 0022152X     EISSN: None     Source Type: Journal    
DOI: 10.1002/jhet.35     Document Type: Article

References (27)

1. (a) Tamm, I. Science 1954, 126, 1235
2. (b) Migawa, M. T.; Giradet, J. L.; Walker, J. A.; Koszalka, G. W.; Chamberlain, S. D.; Drach, J. C.; Townsend, L. B. J Med Chem 1998, 41, 1242
3. Por-cari, A. R.; Devivar R. V.; Kucera, L. S.; Drach, J. C.; Townsend, L. B. J Med Chem 1998, 41, 1252.
4. Kim, J. S.; Gatto, B.; Yu, C.; Liu, A.; Liu, L. F.; LaVioe, E. J Med Chem 1996, 39, 992.
5. Zarrinmayeh, H.; Zimmerman, D. M.; Cantrell, B. E.; Schober, D. A.; Bruns, R. F Bioorg Med Chem Lett 1999, 9, 647.
6. Denny, W. A.; Rewcastle, G. W.; Bagley, B. C J Med Chem 1990, 33, 814.
7. Forseca, T.; Gigante B.; Gilchrist T. L. Tetrahedron 2001, 57, 1793.
8. Zhao, J.; Arnaiz, D.; Griedel, B.; Sakata, B.; Dallas, J.; Whitlow, M.; Trinh, L.; Post, J.; Liang, A.; Morrissey, M.; Shaw, K. Bioorg Med Chem Lett 2000, 10, 963.
9. (a) Grimmet, M. R. In Comprehensive Heterocyclic Chemistry; Katritzky, A. R.; Rees, C. W., Eds.; Pergamon Press: Oxford, 1984; Vol. 5, pp 457-480;
10. (b) Harapanhalli, R. S.; McLaughlin, L. W.; Howell, R. W.; Rao, D. V.; Adelstein, S. J.; Kassis, A. I. J Med Chem 1996, 39, 4804.
11. Verner, E.; Katz, B. A.; Spencer, J. R.; Allen, D.; Hataye, J.; Hruzewicz, W.; Hui, H. C.; Kolesnikov, A.; Li, Y.; Luong, C.; Mar-telli, A.; Radika, K.; Rai, R.; She, M.; Shrader, W.; Sprengeler, P. A.; Trapp, S.; Wang, J.; Young, W. B.; Mackman, R. L. J Med Chem 2001, 44, 2753.
12. Vanden Eynde, J. J.; Delfosse, F.; Lor, P.; Van Haverbeke, Y. Tetrahedron 1995, 51, 5813.
13. Chikashita, H.; Nishida, S.; Miyazaki, M.; Morita, Y.; Itoh, K. Bull Chem Soc Jpn 1987, 60, 737.
14. Patzold, F.; Zeuner, F.; Heyer, T. H.; Niclas, H. J. Synth Commun 1992, 22, 281.
15. Bhatnagar, I.; George, M. V. Tetrahedron 1968, 24, 1293.
16. Stephens, F. F.; Bower, J. D. J Chem Soc 1949, 2971.
17. Beaulieu, P. L.; Haché, B.; von Moos, E. A. Synthesis 2003, 1683.
18. Weidner-Wells, M. A.; Ohemeng, K. A.; Nguyen, V. N.; Fraga-Spano, S.; Macielag, M. J.; Werblood, H. M.; Foleno, B. D.; Webb, G. C.; Barrett, J. F.; Hlasta, D. J. Bioorg Med Chem Lett 2001, 11, 1545.
19. Lin, S.; Yang, L. Tetrahedron Lett 2005, 46, 4315.
20. Gogoi, P.; Konwar, D. Tetrahedron Lett 2006, 47, 79.
21. Du, L-.H.; Wang, Y.-G. Synthesis 2007, 675.
22. Varala, R.; Nasreen, A.; Enugala, R.; Adapa, S. R. Tetrahedron Lett 2007, 48, 69.
23. (a) Anastas, P. T.; Kirchhoff, M. M. Acc Chem Res 2002, 35, 686;
24. (b) Cole, A. C.; Jensen, J. L.; Ntai, I.; Tran, K. L. T.; Weaver, K. J.; Forbes, D. C.; Davis, J. H., Jr. J Am Chem Soc 2002, 124, 5962.
25. Ma, H. Q.; Wang, Y. L.; Li, J. P.; Wang, J. Y. Heterocycles 2007, 71, 135.
26. Tao, G.-H.; He, L.; Liu, W.; Xu, L.; Xiong, W.; Wang, T.; Kou, Y. Green Chem 2005, 8, 639.
27. Alloum, A. B.; Bougrin, K.; Soufiaoui, M. Tetrahedron Lett 2003, 44, 5935.