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Updated: Jul 18, 2026

Microwave-Assisted Preparation of 1-Aryl-1H-pyrazole-5-amines
Published on: June 23, 2019
Reduction of different electron-poor N-heteroarylhydrazines in strong basic conditions
Asier Unciti-Broceta1, María J Pineda de las Infantas, Miguel A Gallo
1School of Chemistry, University of Edinburgh, The King's Buildings, West Mains Road, Edinburgh, UK. asier.ub@ed.ac.uk
Abstract:
The first application of the Wolff-Kishner reduction methodology to electron-poor heteroaromatic compounds is reported. Hydrazino-containing heterocycles with hydrazone-type tautomery have been reduced under basic conditions. This novel chemistry was successfully applied to mono-dehalogenate a number of electron-poor heterocycles in a regioselective manner. According to the experimental results, this reductive process is a base-catalyzed reaction that takes only place in the presence of air, probably through an oxygen-assisted mechanism. As consequence of the specific features of this kind of hydrazone/enehydrazine tautomers, the overall outcome of the process is the synthesis of a Shapiro-type reduction product by simply using a milder version of the Huang-Minlon methodology.
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