Copper-Catalyzed Aerobic Oxidative Carbocyclization Reactions of N-[(E)-Stilben-2-yl]amine Derivatives

Abstract

A synthetic method for highly functionalized 2-quinolinones and quinolines has been developed. The copper(II)-catalyzed aerobic oxidative carbocyclization reactions of α-substituted N-[(E)-stilben-2-yl]acetamides, via the intramolecular carbocupration onto the alkenyl moiety, produced 3-substituted 2-quinolinones. Several useful functional groups including benzoyl, acetyl, cyano, and ethoxycarbonyl groups are compatible with the reaction conditions. This strategy was further applied to N-[(E)-stilben-2-yl]enamines to prepare 2,3-disubstituted quinolines in good yields.

Key words

copper salts - oxidative - cyclization - N-[(E)-stilben-2-yl]amines - quinolines

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