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Two-Step Synthesis of Substituted 3-Aminoindazoles from 2-Bromobenzonitriles

Valerie Lefebvre, Thomas Cailly, Frederic Fabis* and Sylvain Rault

*Centre d'Etudes et de Recherche sur le Médicament de Normandie, UPRES EA 4258, INC3M FR-CNRS 3038, UFR des Sciences Pharmaceutiques, Universit de Caen Basse-Normandie, Boulevard Becquerel 14032 Caen Cedex, France, Email: frederic.fabisunicaen.fr

V. Lefebvre, T. Cailly, F. Fabis, S. Rault, J. Org. Chem., 2010, 75, 2730-2732.

DOI: 10.1021/jo100243c


Abstract

A general two-step synthesis of substituted 3-aminoindazoles from 2-bromobenzonitriles involves a palladium-catalyzed arylation of benzophenone hydrazone followed by an acidic deprotection/cyclization sequence. This procedure offers a general and efficient alternative to the typical SNAr reaction of hydrazine with o-fluorobenzonitriles.

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Key Words

Hydrazones, Indazoles


ID: J42-Y2010-1030