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

Chada Raji Reddy; Jonnalagadda Vijaykumar; René Grée

doi:10.1055/s-0032-1316856

Synthesis, Inhaltsverzeichnis

Synthesis 2013; 45(6): 830-836
DOI: 10.1055/s-0032-1316856

paper

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

Chada Raji Reddy*

^aDivision of Natural Products Chemistry, CSIR-Indian Institute of Chemical Technology, Hyderabad 500007, India

,

Jonnalagadda Vijaykumar

^aDivision of Natural Products Chemistry, CSIR-Indian Institute of Chemical Technology, Hyderabad 500007, India

,

René Grée

^bUniversité 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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Abstract

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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.

Key words

pyrazole - propargylic alcohol - one-pot reaction - acid catalysis - hydrazines

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Referenzen

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