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Paper | Special issue | Vol 37, No. 3, 1994, pp.1541-1548
Published online, 1st January, 1970
DOI: 10.3987/COM-93-S86
Oxidation of N-Acyl Hydrazones of o-Aminoaryl Ketones: Synthesis of 2-Acylaminoindazoles

Antigoni Kotali* and Philip A. Harris

*Laboratory of Organic Chemistry, College of Engineering, University of Thessaloniki, Thessaloniki 54006, Greece


Synthesis of 3-shstituted-2-acylminoindazoles via the lead tetraacetate oxidative cyclization of N-carbonylhydrazones of o-aminoarylketones is reported. A mechanism involving formation of organolead, azoacetate and o-quinonemethide imine intermediates isproposed. The formation of the indazole heterocycle was confirmed by an independent synthesis of 2-benzoylamino-3-phenylindazole.