Manganese(III) Acetate Mediated Oxidative Radical Cyclizations of N-(2-Alkenylaryl)-Substituted Enamines

Abstract

A method has been developed for the synthesis of highly functionalized quinolines from readily available N-(2-alkenylaryl)-substituted enamines via a 6-exo-trig radical cyclization of an imine radical. Several useful functional groups including morpholinocarbonyl, benzoyl, and cyano, are compatible with the reaction conditions. Under the Mn(II)/Co(II)/O₂ redox system, these N-(2-alkenylaryl)enamines were also converted into the corresponding quinolines effectively. This strategy was further applied to related 1,4-naphthoquinone derivatives, and benzo[b]acridine-6,11-diones were formed in good yields.

Key words

manganese(III) acetate - oxidative - free radical - enamines - quinolines

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