Hypervalent Iodiine Oxidative Rearrangement of Anthranilamides, Salicylamides and Some #beta#-Substituted Amides:A New and Convenient Synthesis of 2-Benzimidazolones, 2-Benzoxazolones and Related Compounds

摘要

Oxidation of anthranilamides, salicylamides and some #beta#-substituted amides with iodobenzene diacetate in methanolic ptassium hydroxide led to a new and convenient synthesis of 2-benzimidazolones, 2-benzoxazolones and related compounds, respectively. The reaction probably occurs via initial Hofmann-type rearrangement followed by intramolecular cyclization of intermediate isocyanate.