Oxidations With Lead-Tetraacetate. VI. Oxidations of Benzimidazoles, Benzoxazoles and Benzothiazoles

Abstract

Benzimidazole is slowly oxidized in the imidazole ring by lead tetraacetate to benzimidazol-2(3H)-one, 1-acetylbenzimidazol-2(3H)-one and N,N′-(o- phenylene ) bisacetamide . With excess oxidant, oxidation also occurs in the benzene ring at C5. Benzoxazole is much more reactive and gives a variety of products formed by oxidation of both rings. Benzothiazole is the least reactive system and suffers only minimal oxidation at C2 of the thiazole ring.