Reduction of Different Electron-Poor N-Heteroarylhydrazines in Strong Basic Conditions

Asier Unciti-Broceta, Maria Jose Pineda-de-las-Infantas, Miguel Angel Gallo, Antonio Espinosa

Research output: Contribution to journalArticlepeer-review


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.
Original languageEnglish
Pages (from-to)1754–1762
JournalChemistry - A European Journal
Issue number6
Early online date5 Dec 2006
Publication statusPublished - 2007


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