Journal of the Iranian Chemical Society

, Volume 8, Issue 3, pp 648–652 | Cite as

SbCl5.SiO2: an efficient alternative for one-pot synthesis of 1,2,4,5-tetrasubstituted imidazoles in solvent or under solvent-free condition

  • B. Sadeghi
  • B. B. F. Mirjalili
  • S. Bidaki
  • M. Ghasemkhani
Article
First Online:
Revised:
Accepted:

Abstract

In a one-pot four-component reaction, an aldehyde, an amine, benzil and ammonium acetate were condensed for the synthesis of 1,2,4,5-tetrasubstituted imidazoles in the presence of silica supported antimony pentachloride (SbCl5.SiO2) in improved yields. The catalyst is recoverable by simple filtration and can be used in the subsequent reactions.

Keywords

1,2,4,5-Tetrasubstituted imidazoles SbCl5.SiO2 Benzil One-pot synthesis Aldehyde 
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References

  1. [1]
    S.E. Wolkenberg, D.D. Wisnoski, W.H. Leister, Y. Wang, Z. Zhao, C.W. Lindsley, Org. Lett. 6 (2004) 1453.Google Scholar
  2. [2]
    S. Balalaei, A. Arabanian, Green Chem. 2 (2000) 274.Google Scholar
  3. [3]
    A.R. Karimi, Z. Alimohammadi, J. Azizian, A.A. Mohammadi, M.R. Mohmmadizadeh, Catal. Commun. 7 (2006) 728.Google Scholar
  4. [4]
    M. Kidwai, P. Mothsra, V. Bansal, R.K. Somvanshi, A.S. Ethayathulla, S. Dey, T.P. Singh, J. Mol. Catal. A: Chem. 265 (2007) 177.Google Scholar
  5. [5]
    L. Nagarapu, S. Apuri, S. Kantevari, J. Mol. Catal. A: Chem. 266 (2007) 104.Google Scholar
  6. [6]
    M.M. Heravi, F. Derikvand, F.F. Bamoharram, J. Mol. Catal. A: Chem. 263 (2007) 112.Google Scholar
  7. [7]
    S. Kantevari, S.V.N. Vuppalapati, D.O. Biradar, L. Nagarapu, J. Mol. Catal. A: Chem. 266 (2007) 109.Google Scholar
  8. [8]
    S. Das Sharma, P. Hazarika, D. Konwar, Tetrahedron Lett. 49 (2008) 2216.Google Scholar
  9. [9]
    B. Sadeghi, B.B.F. Mirjalili, M.M. Hashemi, Tetrahedron Lett. 49 (2008) 2575.Google Scholar
  10. [10]
    S. Samai, G.C. Nandi, P. Singh, M.S. Singh, Tetrahedron 65 (2009) 10155.Google Scholar
  11. [11]
    A. Corma, H. Garcia, Adv. Synth. Catal. 348 (2006) 1391.Google Scholar
  12. [12]
    G. Srinivas, M. Periasamy, Tetrahedron Lett. 43 (2002) 2785.Google Scholar
  13. [13]
    M.A. Walker, C.H. Heathcock, J. Org. Chem. 56 (1991) 5747.Google Scholar
  14. [14]
    M.A. Bigdeli, A. Rahmati, H. Abbasi-Ghadim, G.H. Mahdavinia, Tetrahedron Lett. 48 (2007) 4575.Google Scholar
  15. [15]
    B. Sadeghi, B.B.F. Mirjalili, M.M. Hashemi, J. Iran. Chem. Soc. 5 (2008) 694.CrossRefGoogle Scholar
  16. [16]
    R.M. Silverstein, G.C. Bassler, T.C. Morrill, Spectrometric Identification of Organic Compounds, 5th ed., Wiley, New York, 1963, p. 162.Google Scholar
  17. [17]
    Y. Kawasaki, Y. Yamamoto, M. Wada, Bull. Chem. Soc. Jpn. 56 (1983) 145.Google Scholar

Copyright information

© Iranian Chemical Society 2011

Authors and Affiliations

  • B. Sadeghi
    • 1
  • B. B. F. Mirjalili
    • 2
  • S. Bidaki
    • 1
  • M. Ghasemkhani
    • 1
  1. 1.Department of ChemistryIslamic Azad University, Yazd BranchYazdIran
  2. 2.Department of Chemistry, College of ScienceYazd UniversityYazdIran

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