Synthesis 2013; 45(6): 830-836
DOI: 10.1055/s-0032-1316856
paper
© Georg Thieme Verlag Stuttgart · New York

Facile One-Pot Synthesis of 3,5-Disubstituted 1H-Pyrazoles from Propargylic Alcohols via Propargyl Hydrazides

Authors

  • Chada Raji Reddy*

    a   Division of Natural Products Chemistry, CSIR-Indian Institute of Chemical Technology, Hyderabad 500007, India
  • Jonnalagadda Vijaykumar

    a   Division of Natural Products Chemistry, CSIR-Indian Institute of Chemical Technology, Hyderabad 500007, India
  • René Grée

    b   Université de Rennes 1, Institut des Sciences Chimiques de Rennes, CNRS UMR 6226, Avenue du Général Leclerc, 35042 Rennes Cedex, France   Fax: +91(40)27160512   eMail: rajireddy@iict.res.in
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Publikationsverlauf

Received: 17. Dezember 2012

Accepted after revision: 25. Januar 2013

Publikationsdatum:
08. Februar 2013 (online)


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Abstract

A new and efficient metal-free, two-component, one-pot approach to a variety of 3,5-disubstituted 1H-pyrazoles has been developed from propargylic alcohols. This transformation proceeds via an acid-catalyzed propargylation of N,N-diprotected hydrazines followed by base-mediated 5-endo-dig cyclization leading to 3,5-disubstituted 1H-pyrazoles in good overall yields.

Supporting Information