Journal of the Iranian Chemical Society

, Volume 7, Issue 4, pp 834–839 | Cite as

Metal-free catalytic oxidation of urazoles under mild and heterogeneous conditions via combination of ammonium nitrate and catalytic amounts of silica sulfuric acid

  • A. Ghorbani-Choghamarani
  • M. A. Zolfigol
  • M. Hajjami
  • S. Mallakpour
Article
Received:
Accepted:

Abstract

Highly efficient production of 4-substituted-1,2,4-triazole-3,5-diones from urazole derivatives using ammonium nitrate and silica sulfuric acid (SiO2-OSO3H), as a cheap and nontoxic catalyst, in the presence of wet SiO2 (50% w/w) under mild and heterogeneous conditions is reported. The process presented here is operationally simple, environmentally benign and produces high yield.

Keywords

Urazole Bis-urazole Triazolinedione Ammonium nitrate Silica sulfuric acid 
This is a preview of subscription content, log in to check access.

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

References

  1. [1]a)
    Z.-J. Quan, Y.-X. Da, Z. Zhang, X.-C. Wang, Catal. Commun. 10 (2009) 1146Google Scholar
  2. b).
    S. Tangestaninejad, M. Moghadam, V. Mirkhani, I. Mohammadpoor-Baltork, K. Ghani, J. Iran. Chem. Soc. 5 (2008) S71.Google Scholar
  3. [2]
    M.A. Zolfigol, Tetrahedron 57 (2001) 9509.Google Scholar
  4. [3]
    A.P. Amrute, S. Sahoo, A. Bordoloi, Y.K. Hwang, J.-S. Hwang, S.B. Halligudi, Catal. Commun. 10 (2009) 1404.Google Scholar
  5. [4]a)
    P.R. Likhar, S. Roy, M. Roy, M.S. Subhas, M.L. Kantam, R.L. De, Synlett (2007) 2301Google Scholar
  6. b).
    B. Sadeghi, B.F. Mirjalili, M.M. Hashemi, J. Iran. Chem. Soc. (5 (2008) 694Google Scholar
  7. c).
    A.R. Massah, M. Dabagh, S. Shahidi, H. Javaherian Naghash, A.R. Momeni, H. Aliyan, J. Iran. Chem. Soc. 6 (2009) 405Google Scholar
  8. d).
    H. Firouzabadi, M. Jafarpour, J. Iran. Chem. Soc. 5 (2008) 159Google Scholar
  9. e).
    F. Shirini, M.A. Zolfigol, A.-R. Abri, J. Iran. Chem. Soc. 5 (2008) 96Google Scholar
  10. f).
    A. Hasaninejad, A. Zare, M.R. Mohammadizadeh, Z. Karami, J. Iran. Chem. Soc. 6 (2009) 153Google Scholar
  11. g).
    S.R. Sarda, W.N. Jadhav, N.B. Kolhe, M.G. Landge, R.P. Pawar, J. Iran. Chem. Soc. 6 (2009) 477.Google Scholar
  12. [5]
    M.M. Heravi, K. Bakhtiari, H.A. Oskooie, S. Taheri, J. Mol. Catal. A-Chem. 263 (2007) 279.Google Scholar
  13. [6]
    Y. Wei, D.M. Lemal, Org. Lett. 6 (2004) 3837.Google Scholar
  14. [7]
    G.C. Vougioukalakis, M.M. Roubelakis, M.N. Alberti, M. Orfanopoulos, Chem. Eur. J. 14 (2008) 9697.Google Scholar
  15. [8]
    Z. Syrgiannis, F. Koutsianopoulos, K.W. Muir, Y. Elemes, Tetrahedron Lett. 50 (2009) 277.Google Scholar
  16. [9]
    C. Menard-Moyon, M. Gross, M. Bernard, P. Turek, E. Doris, C. Mioskowski, Eur. J. Org. Chem. (2007) 4817.Google Scholar
  17. [10]
    M.A. Zolfigol, A. Ghorbani-Choghamarani, M. Shahamirian, M. Safaiee, I. Mohammadpoor-Baltork, S.E. Mallakpour, M. Abdollahi-Alibeik, Tetrahedron Lett. 46 (2005) 5581.Google Scholar
  18. [11]
    R.C. Cookson, I.D.R. Stevens, C.T. Watts, Chem. Commun. (1966) 744.Google Scholar
  19. [12]
    A. Christoforou, G. Nicolaou, Y. Elemes, Tetrahedron Lett. 47 (2006) 9211.Google Scholar
  20. [13]
    A. Ghorbani-Choghamarani, M.A. Zolfigol, T. Rastegar, Chin. J. Catal. 30 (2009) 273.Google Scholar
  21. [14]
    A. Ghorbani-Choghamarani, H. Goudarziafshar, M. Nikoorazm, S. Yousefi, Lett. Org. Chem. 6 (2009) 335.Google Scholar
  22. [15]
    A. Ghorbani-Choghamarani, M. Hajjami, H. Goudarziafshar, M. Nikoorazm, S. Mallakpour, F. Sadeghizadeh, G. Azadi, Monatsh. Chem. 140 (2009) 607.Google Scholar
  23. [16]
    A. Ghorbani-Choghamarani, S. Rezaei, J. Chin. Chem. Soc. 56 (2009) 251.Google Scholar
  24. [17]
    A. Ghorbani-Choghamarani, M. Nikoorazm, H. Goudarziafshar, L. Shiri, Z. Chenani, Bull. Korean Chem. Soc. 30 (2009) 972.Google Scholar
  25. [18]
    A. Ghorbani-Choghamarani, H. Goudarziafshar, S. Rezaei, S.S. Mortazavi, Chin. Chem. Lett. 20 (2009) 415.Google Scholar
  26. [19]
    D. Habibi, M.A. Zolfigol, M. Safaiee, A. Shamsian, A. Ghorbani-Choghamarani, Catal. Commun. 10 (2009) 1257.Google Scholar
  27. [20]
    A. Ghorbani-Choghamarani, M. Nikoorazm, H. Goudarziafshar, B. Tahmasbi, Bull. Korean Chem. Soc. 30 (2009) 1388.Google Scholar

Copyright information

© Iranian Chemical Society 2010

Authors and Affiliations

  • A. Ghorbani-Choghamarani
    • 1
  • M. A. Zolfigol
    • 2
  • M. Hajjami
    • 2
  • S. Mallakpour
    • 3
  1. 1.Department of Chemistry, Faculty of ScienceIlam UniversityIlamIran
  2. 2.Faculty of ChemistryBu-Ali Sina UniversityHamadanIran
  3. 3.Organic Polymer Chemistry Research Laboratory, Department of ChemistryIsfahan University of TechnologyIsfahanIran

Personalised recommendations