Chemoselective Condensation of 3-Amino-2-cyclohexenones with Cinnamaldehydes: Switchable Synthesis of Dihydroquinolinones and Hexahydroacridinediones

By:Jiang, Ling; He, Kun; Zeng, Weikun; Qiao, Zhi; Song, Xizhong; Luo, Kaixiu; Chen, Jingbo; Lin, Jun*; Jin, Yi*

The Journal of Organic Chemistry

DOI：10.1021/acs.joc.3c00011

Published：2023-May-05

Abstract

Herein, a chemoselective condensation of 3-amino-2-cyclohexenones and cinnamaldehydes for switchable synthesis of dihydroquinolinones and hexahydroacridinediones was developed. Mechanism analysis showed that the formation of dihydroquinolinones involved trimolecular condensation and oxidative aromatization, while the formation of hexahydroacridinediones involved acid hydrolysis of enaminone and dehydration-aromatization. This strategy provides a convenient way to switch from the same substrates to produce two different quinolinone derivatives.

全文链接：https://pubs.acs.org/doi/10.1021/acs.joc.3c00011