Elsevier

Tetrahedron Letters

Volume 47, Issue 5, 30 January 2006, Pages 833-836
Tetrahedron Letters

4-(p-Chloro)phenyl-1,2,4-triazole-3,5-dione as a novel and reusable reagent for the oxidation of 1,3,5-trisubstituted pyrazolines under mild conditions

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Abstract

4-(p-Chloro)phenyl-1,3,4-triazole-3,5-dione is used as an effective oxidizing agent for the oxidation of 1,3,5-trisubstituted pyrazolines to their corresponding pyrazoles under mild conditions with moderate to good yields at room temperature.

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Acknowledgement

Financial support for this work by the Research Council of Bu-Ali Sina University, Hamadan, Iran, is gratefully acknowledged.

References and notes (22)

  • S.E. Mallakpour et al.

    Indian J. Chem.

    (1995)
    S.E. Mallakpour et al.

    Indian J. Chem.

    (1995)
    S.E. Mallakpour et al.

    Indian J. Chem.

    (1998)
    S.E. Mallakpour et al.

    Indian J. Chem.

    (1999)
    M.A. Zolfigol et al.

    Synth. Commun.

    (2003)
    M.A. Zolfigol et al.

    Synlett

    (2005)
  • N. Nakamichi et al.

    Synthesis

    (2004)
  • T.L. Gilchrist

    Heterocyclic Chemistry

    (1992)
    X.C. Gao et al.

    J. Mater. Chem.

    (1999)
    R.M. Claramunt et al.

    J. Chem. Soc., Perkin Trans. 2

    (2000)
    J.A. Froggett et al.

    J. Chem. Res. (S)

    (1997)
    J.E. Baldwin et al.

    J. Chem. Soc., Perkin Trans. 1

    (2001)
    S.A. Voznesenskii et al.

    Mendeleev Commun.

    (1998)
    A.C. Donohue et al.

    J. Chem. Soc., Perkin Trans. 1

    (2001)
    G.H. Elgemeie et al.

    J. Chem. Res. (S)

    (1999)
    K.T. Chang et al.

    J. Chem. Soc., Perkin Trans. 1

    (2002)
  • N. Nakamichi et al.

    Org. Lett.

    (2002)
  • J.N. Shah et al.

    J. Org. Chem.

    (1978)
  • W.A.F. Goldstone et al.

    J. Chem. Soc., Chem. Commun.

    (1966)
  • K. Auwers et al.

    Liebigs Ann.

    (1927)
  • I.G. Bhatnagar et al.

    Tetrahedron

    (1968)
  • L.I. Smith et al.

    J. Am. Chem. Soc.

    (1943)
  • R.P. Dodwadmath et al.

    Proc. Ind. Acad. Sci.

    (1935)
  • S.P. Singh et al.

    Synth. Commun.

    (1997)
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