Chinese Journal of Organic Chemistry ›› 2021, Vol. 41 ›› Issue (2): 677-687.DOI: 10.6023/cjoc202008020 Previous Articles     Next Articles



史鸿燕1, 钟莹1,*(), 赵志刚1,*()   

  1. 1 西南民族大学化学与环境保护工程学院 成都 610041
  • 收稿日期:2020-08-12 修回日期:2020-09-08 发布日期:2020-09-30
  • 通讯作者: 钟莹, 赵志刚
  • 作者简介:
    * Corresponding authors. E-mail: ;
  • 基金资助:

Synthesis of Multi-substituted 1,4-Dihydroquinoline Derivatives from Morita-Baylis-Hillman (MBH) Carbonates

Hongyan Shi1, Ying Zhong1,*(), Zhigang Zhao1,*()   

  1. 1 College of Chemistry & Environment Protection Engineering, Southwest Minzu University, Chengdu 610041
  • Received:2020-08-12 Revised:2020-09-08 Published:2020-09-30
  • Contact: Ying Zhong, Zhigang Zhao
  • Supported by:
    the Fundamental Research Funds for the Central Universities, Southwest Minzu University(2018NQN35)

Using Morita-Baylis-Hillman (MBH) carbonates and active methylene compounds as raw materials, the key azide intermediates were obtained through two nucleophilic substitution reactions catalyzed by tertiary amine. Then, seventeen new multi-substituted 1,4-dihydroquinoline derivatives were obtained by sequential Staudinger/intramolecular aza-Wittig/isomeri- zation reactions of the azide intermediates with triphenylphosphine under mild conditions. The intermediates and target compounds are all new compounds, and their structures have been confirmed by IR, HRMS, 1H NMR and 13C NMR techniques.

Key words: 1,4-dihydroquinolines, aza-Wittig reaction, Morita-Baylis-Hillman (MBH) carbonate, azide