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Direct Alkenylation of 2‐Methylquinolines with Aldehydes through Synergistic Catalysis of 1,3‐Dimethylbarbituric Acid and HOAc
Author(s) -
Liang En,
Wang Junqi,
Wu Yinrong,
Huang Liangbin,
Yao Xingang,
Tang Xiaodong
Publication year - 2019
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201900351
Subject(s) - chemistry , catalysis , functional group , atom economy , transformation (genetics) , reaction conditions , organic chemistry , organocatalysis , combinatorial chemistry , medicinal chemistry , computational chemistry , polymer , biochemistry , gene , enantioselective synthesis
An efficient and practical direct alkenylation of 2‐methylquinolines with aldehydes has been achieved through a novel synergistic organocatalysis. The HOAc‐ activated 2‐methylquiolines undergo a Michael addition to 1,3‐dimethylbarbituric acid‐activated aldehydes, followed by a retro‐Michael addition to release 1,3‐dimethylbarbituric acid and the target products. The transformation produced various 2‐alkenylquinolines with good to excellent yields and featured mild reaction conditions, atom‐ and step‐economy, good functional group tolerance, and operational simplicity.