New practical synthesis of indazoles via condensation of o-fluorobenzaldehydes and their o-methyloximes with hydrazine

…, MC Hsu, D Fernando, MR Leanna

Index: Lukin, Kirill; Hsu, Margaret C.; Fernando, Dilinie; Leanna, M. Robert Journal of Organic Chemistry, 2006 , vol. 71, # 21 p. 8166 - 8172

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Citation Number: 74

Abstract

The reaction of o-fluorobenzaldehydes and their O-methyloximes with hydrazine has been developed as a new practical synthesis of indazoles. Utilization of the methyloxime derivatives of benzaldehydes (in the form of the major E-isomers) in this condensation effectively eliminated a competitive Wolf-Kishner reduction to fluorotoluenes, which was observed in the direct preparations of indazoles from aldehydes. Reaction of Z-isomers of ...