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Synthesis of Quinoline and 1,2,3,4‐Tetrahydroquinoline Derivatives from Substituted o ‐Nitrotoluenes via Cesium‐promoted [2 + 4] Cycloaddition
Author(s) -
Guo Weijie,
Yi Maocong,
Wang Jianhui,
Liu Guiyan
Publication year - 2017
Publication title -
chinese journal of chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.28
H-Index - 41
eISSN - 1614-7065
pISSN - 1001-604X
DOI - 10.1002/cjoc.201700150
Subject(s) - chemistry , quinoline , cycloaddition , caesium , combinatorial chemistry , organic chemistry , catalysis
An atom economical highly efficient method has been developed for the synthesis of quinoline and 1,2,3,4‐tetrahydroquinoline derivatives from o ‐nitrotoluenes bearing electron‐withdrawing groups and olefins (acrylic esters, acrylonitriles, and methyl acrylates) via a base‐catalyzed [2 + 4] cycloaddition. This simple, rapid, and environment‐ friendly method provides a practical pathway for the synthesis of quinoline and 1,2,3,4‐tetrahydroquinoline derivatives. The starting materials are readily available and 37 products were obtained in good to excellent yields.