Synthesis of 2-Substitued Benzimidazoles Using P2O5-SiO2

Iranian Journal of Catalysis

مقاله 6، دوره 2، شماره 1، فروردین 2012، صفحه 31-35   

نویسندگان

Ahmad Reza Momeni^{* 1}؛ Somayeh Bagheri²

¹Faculty of Science, Shahrekord University, Shahrekord 115-381, Iran

²Faculty of Science, Shahreza Branch Islamic Azad University, 86145-311, Iran

چکیده

P₂O₅-SiO₂ (30% w/w) was found to be a useful catalyst for the synthesis of various 2-substituted aryl benzimidazoles under solvent-less and in solvent conditions from o-phenylenediamine and aldehydes. The products were directly recrystallized from methanol.

کلیدواژه‌ها

P2O5/SiO2؛ Solvent-free؛ Benzimidazole؛ o-Phenylenediamine؛ Supported catalyst

مراجع

1. C.A. Mathis, Y. Wang, D.P. Holt, G.F Huang, M.L. Debnath, W.E. Klunk, J. Med. Chem. 46 (2003) 2740-2754.

2. S.A. Hutchinson, B.R. Jennings, A.D. Vishnuvajjala, M.F.G. Westwell, J. Stevens, J. Med. Chem. 45 (2002) 744-747.

3. G.L. Gravatt, B.C. Baguley, W.R. Wilson, W.A Denny. J. Med. Chem. 37 (1994) 4338-4345.

 

 

 

4. J.S. Kim, B. Gatto, C. Yu, A. Liu, L.F. Liu, E.J. La Voie, J. Med. Chem. 39 (1996) 992-998.

5. T. Roth, M.L. Morningstar, P.L. Boyer, S.H. Hughes, R.W. Buckheit, C.J. Michejda, J. Med. Chem. 40 (1997) 4199-4207.

6. D.A. Horton, G.T. Bourne, M.L. Smythe, Chem. Rev. 103 (2003) 893-930.

7. S. Heuser, M. Keenan, A.G. Weichert, Tetrahedron Lett. 46 (2005) 9001-9004.

8. R.N. Nadaf, S.A. Siddiqui, T. Daniel, R.J. Lahoti, K.V. Srinivasan, J. Mol. Catal. A 214 (2004) 155-160.

9. B. Das, H. Holla, Y. Srinivas, Tetrahedron Lett. 48 (2007) 61–64.

10. M.A. Chari, D. Shobha, El-R. Kenawy, S.S. Al-Deyab, B.V. Subba Reddy, A. Vinu , Tetrahedron Lett. 51 (2010) 5195–5199.

11. R. Fazaeli, H. Aliyan, Appl. Catal. A 353 (2009) 74–79.

12. H. Aliyan R. Fazaeli, N. Fazaeli, A.R. Mssah, H.J. Naghash, M. Alizadeh, G. Emami, Heteroatom Chem. 20 (2009) 202-207.

13. M-G. Shen, C. Cai, J. Fluorine Chem. 128 (2007) 232–235.

14. R. Varala, A. Nasreen, R. Enugala, S.R. Adapa, Tetrahedron Lett. 50 (2009) 1495–1497.

15. R.G. Jacob, L.G Dutra, C.S. Radatz, S.R. Mendes, G. Perin, E.J. Lenardão, Tetrahedron Lett. 50 (2009), 1495–1497.

16. K.D. Parghi, R.V. Jayaram, Catal. Commun. 11 (2010) 1205–1210.

17. P. Ghosh, A. Mandal, Catal. Commun. 12 (2011) 744–747.

18. P. K. Ranjith, M. Siji, N. Divia, R.H. Karickal, J. Korean Chem. Soc. 54 (2010) 589- 593.

19. R. Varala, A. Nasreen, R. Enugala, S.R. Adapa, Tetrahedron Lett. 48 (2007) 69–72.

20. D.S. VanVliet, P. Gillespieb, J.J. Scicinskia, Tetrahedron Lett. 46 (2005) 6741–6743.

21. G. Navarrete-Vazquez, H. Moreno-Diaz, F. Aguirre-Crespo, I. Leon-Rivera, R. Villalobs-Molina, O. Munoz-Munizd, S. Estrada-Soto, Bioorg. Med. Chem. Lett. 16 (2006) 4169-4173.

22. Z.H. Zhang, L. Yin, Y.M. Wang, Catal. Commun. 8 (2007) 1126–1131.

23. A.R. Hajipour, B. Kooshki, A.E. Ruoho, Tetrahedron Lett. 46 (2005) 5503-5506.

24. H. Eshghi, A. Hassankhani, Synth. Commun. 36 (2006) 2211-2216.

25. M. Mirjalili, M.A. Zolfigol, A. Bamoniri, Phosphorus, Sulfur, and Silicon 179 (2004) 19-24.

26. A.R. Massah, M, Dabagh, S. Shahidi, H.J. Naghash, A.R. Momeni, H. Aliyan, J. Iran. Chem. Soc., 6 (2009) 405-411.

27. A.R. Momeni, M.  Sadeghi, Appl. Catal. A 357 (2009) 100–105.

28. A.R Momeni,. M. Sadeghi, M. Hadizadeh, Turk. J. Chem. 33 (2009) 751– 758.

29. A.R. Massah, F. Kazemi, D. Azadi, S. Farzaneh, H. Aliyan, H.J. Naghash,  A.R. Momeni, Lett. Org. Chem. 3 (2006) 235–241.

30. A.R. Massah, M. Dabagh, M. Afshar, A.R. Momeni, H. Aliyan, H.J. Naghash, Turk. J. Chem. 31 (2007) 611– 616.

31. A.R. Massah, M. Mosharafian, A.R. Momeni,  H. Aliyan,  H. J. Naghash,  M. Adibnejad, Synth. Commun. 37 (2007) 1807-1815.

32. A.R. Massah, A.R. Momeni, M. Dabagh, H. Aliyan, H.J. Naghash, Synth. Commun. 38 (2008) 265-273.

33. R.R. Nagawade, D. B. Shinde, Chinese Chem. Lett. 17 (2006) 453-456.

34. V.K. Tandon, M. Kumar, Tetrahedron Lett. 45 (2004)
4185–4187.

35. S.D. Sharmaa, D. Konwara, Synth. Commun. 1 (2009)
980–991.