Brønsted Acid Mediated Nucleophilic Functionalization of Amides through Stable Amide C−N Bond Cleavage; One-Step Synthesis of 2-Substituted Benzothiazoles

Abstract

We have developed a Brønsted acid mediated synthetic method to directly cleave stable amide C−N bonds by a variety of alcohol and amine nucleophiles. Reverse reactivity was observed and alcoholysis of amides by activated primary and secondary benzylic, and propargylic alcohols have been achieved instead of the expected nucleophilic substitution of alcohols. As an application, 2-substituted benzothiazole derivatives have been synthesized in one pot employing 2-aminothiophenol as nucleophile.