Synthesis 2015; 47(23): 3687-3700
DOI: 10.1055/s-0034-1378870
paper
© Georg Thieme Verlag Stuttgart · New York

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

Cheng-Yen Lu
Department of Chemistry, National Cheng Kung University, Tainan, Taiwan 70101, Taiwan   eMail: cpchuang@mail.ncku.edu.tw
,
Che-Ping Chuang*
Department of Chemistry, National Cheng Kung University, Tainan, Taiwan 70101, Taiwan   eMail: cpchuang@mail.ncku.edu.tw
› Institutsangaben
Weitere Informationen

Publikationsverlauf

Received: 25. Mai 2015

Accepted after revision: 29. Juni 2015

Publikationsdatum:
14. August 2015 (online)


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.

Supporting Information