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

• DOI: 10.1002/ejoc.201901331
• Publication Date: 2019-11-18T03:00:21Z
• Authors: Yinrong Wu; Xianchen Lu; Hang Wang; En Liang; Yingying Yuan; Qiaorun Zhao; Zhongzhi Zhu; Jiaping Huang; Xiaodong Tang
• Keywords: Knoevenagel condensation; Quinoline; Nucleophilic Addition

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 hydroxyquinolines were efficiently prepared moderate good yields. In addition, HOAc/1,3‐DMBBA (1,3‐dimethylbarbituric acid) synergistic organocatalysis system was also developed for the synthesis alkenylquinolines which involved sequence Knoevenagel condensation, Micheal and retro‐Micheal steps.