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    【J.Org.Chem.】Chemoselective Condensation of 3-Amino-2-cyclohexenones with Cinnamaldehydes: Switchable Synthesis of Dihydroquinolinones and Hexahydroacridinediones

    来源: 日期:2023年05月09日 17:18点击:

    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


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