title: New practical synthesis of indazoles via condensation of o-fluorobenzaldehydes and their O-methyloximes with hydrazine.
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 methyloximes with hydrazine resulted in the formation of 3-aminoindazoles via a benzonitrile intermediate.
authors.affiliation: GPRD Process Research and Development, Abbott Laboratories, North Chicago, Illinois 60064, USA. kirill.lukin@abbott.com
authors.forename: Kirill
authors.initials: K
authors.lastname: Lukin
authors.forename: Margaret C
authors.initials: MC
authors.lastname: Hsu
authors.forename: Dilinie
authors.initials: D
authors.lastname: Fernando
authors.forename: M Robert
authors.initials: MR
authors.lastname: Leanna
mesh_terms: D007191:Indazoles / Q000138:chemical synthesis*
chemical_list: D007191:Indazoles