A green route for the one-pot synthesis of 1,2-disubstituted benzimidazoles using iron(III) phosphate under solventless conditions

Chinese Journal of Chemistry

Volumn 30, Issue 1, 2012, Pages 65-70

  Behbahani, F K ^a   Ziaei, Parisa ^a  

^a ISLAMIC AZAD UNIVERSITY   (Iran)

Author keywords

1,2 disubstituted benzimidazoles; iron(III) phosphate; solvent free

Indexed keywords

EID: 84856015514     PISSN: 1001604X     EISSN: 16147065     Source Type: Journal    
DOI: 10.1002/cjoc.201180461     Document Type: Article

References (41)

1. Barker, H. A.,;, Smyth, R. D.,;, Weissbach, H.,;, Toohey, J. I.,;, Ladd, J. N.,;, Volcani, B. E.,. J. Biol. Chem., 1960, 235, 480.
2. Zarrinmayeh, H.,;, Nunes, A. M.,;, Ornstein, P. L.,;, Zimmerman, D. A.,;, Gackenheimer, S. L.,;, Bruns, R. F.,;, Hipskind, P. A.,;, Britton, T. C.,;, Catrell, B. E.,;, Gehlert, D. R.,. J. Med. Chem., 1998, 41, 2709.
3. Nakano, H.,;, Inoue, T.,;, Kawasaki, N.,;, Miyataka, H.,;, Matsumoto, H.,;, Taguchi, T.,;, Inagaki, N.,;, Nagai, H.,;, Satoh, T.,. Bioorg. Med. Chem., 2000, 8, 373.
4. Kohara, Y.,;, Kubo, K.,;, Imamiya, E.,;, Wada, T.,;, Inada, Y.,;, Naka, T.,. J. Med. Chem., 1996, 39, 5228.
5. White, A. W.,;, Almassy, R.,;, Calvert, A. H.,;, Curtin, N. J.,;, Grif-fin, R. J.,;, Hostornsky, Z.,;, Maegley, K.,;, Newell, D. R.,;, Srinivasan, S.,;, Golding, B. T.,. J. Med. Chem., 2000, 43, 4084.
6. Zhao, Z. S.,;, Arainz, D. O.,;, Greidel, B.,;, Sakata, S.,;, Dallas, J. L.,;, Whitelow, M.,;, Trinh, L.,;, Post, J.,;, Liang, A.,;, Morrissey, M. M.,;, Shaw, K. J.,. Bioorg. Med. Chem. Lett., 2000, 10, 963.
7. Tebbe, M. J.,;, Spitzer, W. A.,;, Victor, F.,;, Miller, S. C.,;, Lee, C. C.,;, Sattelberg, T. R.,;, Mckinney, E.,;, Tang, C. J.,. J. Med. Chem., 1997, 40, 3937.
8. Porcari, A. R.,;, Devivar, R. V.,;, Kucera, L. S.,;, Drach, J. C.,;, Townsend, L. B.,. J. Med. Chem., 1998, 41, 1252.
9. 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.
10. Spasov, A. A.,;, Yozhitsa, I. N.,;, Bugaeva, L. I.,;, Anisimova, V. A.,. Pharm. Chem. J., 1999, 33, 232.
11. Evans, B. E.,;, Rittle, K. E.,;, Bock, M. G.,;, Dipardo, R. M.,;, Freidinger, R. M.,;, Whitter, W. L.,;, Lundell, G. F.,;, Veber, D. F.,;, Ander-son, P. S.,;, Chang, R. S.,;, Chang, R. S. L.,;, Lotti, V. J.,;, Gerino, D. J.,;, Chen, T. B.,;, Kling, P. J.,;, Kunkel, K. A.,;, Springer, J. P.,;, Hirshfield, J.,. J. Med. Chem., 1988, 31, 2235.
12. Mason, J. S.,;, Morize, L.,;, Menard, P. R.,;, Cheney, D. L.,;, Hume, C.,;, Labaudiniere, R. F.,. J. Med. Chem., 1999, 42, 3251.
13. Wu, Z.,;, Rea, P.,;, Wickam, G.,. Tetrahedron Lett., 2000, 41, 9871.
14. Mazurov, A.,. Bioorg. Med. Chem. Lett., 2000, 10, 67.
15. Chi, Y. C.,;, Sun, C. M.,. Synlett, 2000, 591.
16. Huang, W.,;, Scarborough, R. M.,. Tetrahedron Lett., 1999, 40, 2665.
17. Dudd, L. M.,;, Venardou, E.,;, Verdugo, E. G.,;, Licence, P.,;, Blake, A. J.,;, Wilson, C.,;, Poliakoff, M.,. Green Chem., 2003, 5, 187.
18. Kim, B. H.,;, Han, R.,;, Kim, J. S.,;, Jun, Y. M.,;, Baik, W.,;, Lee, B. M.,. Heterocycles, 2004, 63, 41.
19. Itoh, T.,;, Nagata, K.,;, Ishikawa, H.,;, Ohsawa, A.,. Heterocycles, 2004, 63, 2769.
20. Salehi, P.,;, Dabiri, M.,;, Zolfigol, M. A.,;, Otokesh, S.,;, Baghbanzadeh, M.,. Tetrahedron Lett., 2006, 47, 2557.
21. Oskooie, H. A.,;, Heravi, M. M.,;, Sadnia, A.,;, Behbahani, F. K.,;, Jannati, F.,. Chin. Chem. Lett., 2007, 18, 1357.
22. Jadhav, G. R.,;, Shaikh, M. U.,;, Kale, R. P.,;, Gill, C. H.,. Chin. Chem. Lett., 2009, 20, 535.
23. Beheshtiha, Y. S.,;, Heravi, M. M.,;, Saeedi, M.,;, Karimi, N.,;, Zakeri, M.,;, Tavakoli-Hossieni, N.,. Synth. Commun., 2010, 40, 1216.
24. Bahrami, K.,;, Khodaei, M. M.,;, Nejati, A.,. Green Chem., 2010, 12, 1237.
25. Bailar, J. C.,;, Emeleus, H. E.,;, Nyholm, R.,;, Trotman-Dickenson, A. F.,. In Comprehensive Inorganic Chemistry, Vol. 3, Pergamon Press, Oxford, 1979, p. 1042.
26. TAP report for Iron(III) phosphate, July, 2004.
27. Otsuka, K.,;, Wang, Y.,. Appl. Catal. A: Gen., 2001, 222, 145.
28. Ren, T.,;, Yan, L.,;, Zhang, X.,;, Suo, J.,. Appl. Catal. A: Gen., 2003, 244, 11.
29. Heravi, M. M.,;, Behbahani, F. K.,;, Zadsirjan, V.,;, Oskooie, H. A.,. Heterocyclic Commun., 2006, 12, 369.
30. Behbahani, F. K.,;, Yektanezhad, T.,;, Khorrami, A. R.,. Heterocycles, 2010, 81, 2313.
31. Heravi, M. M.,;, Zadsirjan, V.,;, Behbahani, F. K.,;, Oskooie, H. A.,. J. Mol. Catal. A: Chem., 2006, 259, 201.
32. Heravi, M. M.,;, Behbahani, F. K.,;, Oskooie, H. A.,. Chin. J. Chem., 2008, 26, 2203.
33. Oskooie, H. A.,;, Heravi, M. M.,;, Behbahani, F. K.,. Molecules, 2007, 12, 1438.
34. Varala, R.,;, Nasreen, A.,;, Enugala, R.,;, Adapa, S. R.,. Tetrahedron Lett., 2007, 48, 69.
35. Perumal, S.,;, Mariappan, S.,;, Selvaraj, S. A.,. Arkivoc, 2004, 8, 46.
36. Sharma, S. D.,;, Konwar, D., Synth. Commun., 2009, 39, 980.
37. Sharghi, H.,;, Asenani, O.,;, Tabaei, S. M. H., J. Hetrocycl. Chem., 2008, 45, 1293.
38. Yadav, J. S.,;, Reddy, B. V. S.,;, Premalatha, K.,;, Shankar, K. S.,. Can. J. Chem., 2008, 86, 124.
39. Kim, B. H.,;, Han, R.,;, Han, T. H.,;, Jun, Y. M.,;, Baik, W.,;, Lee, B. M.,. Heterocycles, 2002, 57, 5.
40. Azarifar, D.,;, Khosravi, K.,;, Najminejad, Z.,;, Soleimani, K.,. Heterocycles, 2010, 81, 2855.
41. Jacob, R. G.,;, Dutra, L. G.,;, Radatz, C. S.,;, Mendes, S. R.,;, Perin, G.,;, Lenard?o, E. J.,. Tetrahedron Lett., 2009, 50, 1495.