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Synthesis of 2-arylbenzimidazoles catalyzed by transition metal nitrates

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Abstract

A simple and practical procedure for synthesis of 2-arylbenzimidazoles by a one-pot condensation of o-phenylenediamine with aromatic aldehydes in the presence of a catalytic amount of M(NO3)2·6H2O (M = Mn, Fe, Co, Ni, Cu) in ethanol at room temperature is described. Major advantages of this practical procedure are use of a readily available catalyst, high yields, short reaction times, and simplicity of the reaction and workup.

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References

  1. G.L. Gravatt, B.C. Baguley, W.R. Denny, J. Med. Chem. 37, 4338 (1994)

    Article  CAS  Google Scholar 

  2. S.M. Abu-Bakr, F.A. Bassyouni, M.A. Rehim, Res. Chem. Intermed. (2012). doi: 10.1007/s11164-012-0569-y

  3. J.S. Kim, B. Gatto, C. Yu, A. Liu, L.F. Liu, V. La, J. Med. Chem. 39, 992 (1996)

    Article  CAS  Google Scholar 

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

    Article  CAS  Google Scholar 

  5. A.R. Porcari, R.V. Devivar, L.S. Kucera, J.C. Drach, B.L. Townsend, J. Med. Chem. 41, 1252 (1998)

    Article  CAS  Google Scholar 

  6. A. Mobinikhaledi, N. Foroughifar, M. Kalhor, M. Mirabolfathy, J. Heterocycl. Chem. 47, 77 (2010)

    CAS  Google Scholar 

  7. J.S. Mason, I. Morize, P.R. Menard, D.L. Cheney, C. Hume, R.F. Labaudiniere, J. Med. Chem. 42, 3251 (1999)

    Article  CAS  Google Scholar 

  8. R. Iemura, T. Kawashima, T. Fukuda, K. Ito, G.J. Tsukamoto, J. Heterocycl. Chem. 24, 31 (2009)

    Article  Google Scholar 

  9. Y. Bai, J. Lu, Z. Shi, B. Yang, Synlett. 544 (2001)

  10. E. Hasegawa, A. Yoneoka, K. Suzuki, T. Kato, T. Kitazume, K. Yangi, Tetrahedron 55, 12957 (2001)

    Article  Google Scholar 

  11. P. Salehi, M. Dabiri, M.A. Zolfigol, S. Otokesh, M. Baghbanzadeh, Tetrahedron Lett. 47, 2557 (2006)

    Article  CAS  Google Scholar 

  12. R.R. Nagawade, D.B. Shinde, Chin. Chem. Lett. 17, 453 (2006)

    CAS  Google Scholar 

  13. G.R. Jadhav, M.U. Shaikh, R.P. Kale, C.H. Gill, Chin. Chem. Lett. 20, 292 (2009)

    Article  CAS  Google Scholar 

  14. M. Shen, C.J. Cai, Fluorine Chem. 128, 232 (2007)

    Article  CAS  Google Scholar 

  15. A. Mobinikhaledi, N. Foroughifar, M. Zendehdel, M. Jabbarpour, Syn. React. Inorg. Met-org. Chem. 38, 390 (2008)

    CAS  Google Scholar 

  16. X. Han, H. Ma, Y. Wang, Russ. J. Org. Chem. 863 (2008)

  17. K.H. Bûchel, Z. Naturforsch. 25B, 934 (1970)

    Google Scholar 

  18. A. Mobinikhaledi, A. Khajeh-Amiri, Res. Chem. Intermed. (2012). doi 10.1007/s11164-012-0707-6

  19. A. Mobinikhaledi, M. Zendehdel, J.F. Hasanvand, Syn. React. Inorg. Met-org. Chem. 37, 175 (2007)

    Article  CAS  Google Scholar 

  20. A. Mobinikhaledi, N. Foroughifar, M.A. Amrollahi, Asian J. Chem. 17, 1301 (2005)

    CAS  Google Scholar 

  21. M. Zendehdel, A. Mobinikhaledi, J.F. Hasanvand, J. Incl. Phenom. Macro 59, 41 (2007)

    Article  CAS  Google Scholar 

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Correspondence to Mehdi Kalhor.

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Kalhor, M., Mobinikhaledi, A. & Jamshidi, J. Synthesis of 2-arylbenzimidazoles catalyzed by transition metal nitrates. Res Chem Intermed 39, 3127–3133 (2013). https://doi.org/10.1007/s11164-012-0825-1

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  • DOI: https://doi.org/10.1007/s11164-012-0825-1

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