Acid‐Catalyzed Synthesis of Quinoline Derivatives from 2‐Methylquinolines and 2‐Aryloxy/Alkoxybenzaldehyde in Aqueous Medium | Zendy

Wu Yinrong | Zendy; Lu Xianchen | Zendy; Wang Hang | Zendy; Liang En | Zendy; Yuan Yingying | Zendy; Zhao Qiaorun | Zendy; Zhu Zhongzhi | Zendy; Huang Jiaping | Zendy; Tang Xiaodong | Zendy

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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.

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