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

A synthetic method for highly functionalized 2-quinolinones and quinolines has been developed. The copper(II)-catalyzed aerobic oxidative carbocyclization reactions of -substituted N-[(E)-stilben-2-yl]acetamides, via the intramolecular carbocupration onto the alkenyl moiety, produced 3-substituted 2...

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Published inSynthesis (Stuttgart) Vol. 47; no. 23; pp. 3687 - 3700
Main Authors Lu, Cheng-Yen, Chuang, Che-Ping
Format Journal Article
LanguageEnglish
Published STUTTGART Thieme Medical Publishers 01.12.2015
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
N-ARYL ENAMINES
C BOND FORMATION
COUPLING-CYCLIZATION
TRIFLUOROACETIC-ACID
ALKYNES
cyclization
N-[(E)-stilben-2-yl]amines
POLYSUBSTITUTED PYRROLES
METHYL PERFLUOROALK-2-YNOATES
QUINOLINE
CYCLIZATION REACTIONS
oxidative
FREE-RADICAL REACTIONS
copper salts
quinolines
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Summary:A synthetic method for highly functionalized 2-quinolinones and quinolines has been developed. The copper(II)-catalyzed aerobic oxidative carbocyclization reactions of -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.
ISSN:0039-7881
1437-210X
DOI:10.1055/s-0034-1378870