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

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
› Author Affiliations
Further Information

Publication History

Received: 17 December 2012

Accepted after revision: 25 January 2013

Publication Date:
08 February 2013 (online)


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

 
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