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Acid‐Catalyzed Synthesis of Quinoline Derivatives from 2‐Methylquinolines and 2‐Aryloxy/Alkoxybenzaldehyde in Aqueous Medium
Author(s) -
Wu Yinrong,
Lu Xianchen,
Wang Hang,
Liang En,
Yuan Yingying,
Zhao Qiaorun,
Zhu Zhongzhi,
Huang Jiaping,
Tang Xiaodong
Publication year - 2019
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.201901331
Subject(s) - chemistry , knoevenagel condensation , quinoline , catalysis , nucleophile , organocatalysis , combinatorial chemistry , organic chemistry , nucleophilic addition , aqueous solution , alkoxy group , alkyl , enantioselective synthesis
A HOAc‐catalyzed aryloxy/alkoxy‐assisted nucleophilic addition of 2‐methylquinolines to aldehydes in water has been described. With this highly environmentally benign protocol, a series of hydroxyquinolines were efficiently prepared in moderate to good yields. In addition, a HOAc/1,3‐DMBBA (1,3‐dimethylbarbituric acid) synergistic organocatalysis system was also developed for the synthesis of alkenylquinolines which involved a sequence of Knoevenagel condensation, Micheal addition, and retro‐Micheal addition steps.