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p ‐Toluenesulfonic Acid Promoted Annulation of 2‐Alkynylanilines with Activated Ketones: Efficient Synthesis of 4‐Alkyl‐2,3‐Disubstituted Quinolines
Author(s) -
Peng Changlan,
Wang Yong,
Liu Lanying,
Wang Honggen,
Zhao Jiaji,
Zhu Qiang
Publication year - 2010
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.200901257
Subject(s) - chemistry , p toluenesulfonic acid , alkyl , aminoquinolines , quinoline , aryl , annulation , combinatorial chemistry , organic chemistry , medicinal chemistry , catalysis
Reactions between readily available 2‐alkynylanilines and activated ketones such as β‐keto esters promoted by p ‐toluenesulfonic acid afford 4‐alkyl‐2,3‐disubstituted quinolines in good to excellent yields. The generality of substituents at the other end of the triple bond of 2‐alkynylanilines makes the method a valuable approach to diversified 4‐alkylquinolines, which are difficult to obtain by classical methods such as the Friedländer reaction. Quinoline dimers can be prepared efficiently with alkyl or aryl linkers at C‐4.