Chin. J. Org. Chem. ›› 2017, Vol. 37 ›› Issue (4): 881-888.DOI: 10.6023/cjoc201611003 Previous Articles     Next Articles



陈雪冰a, 白海瑞b, 黄超b   

  1. a. 红河学院理学院 云南省天然药物与化学生物学重点实验室 蒙自 661100;
    b. 云南民族大学化学与环境学院 云南省生物高分子功能材料工程技术研究中心 昆明 650503
  • 收稿日期:2016-11-01 修回日期:2016-12-27 发布日期:2017-01-17
  • 通讯作者: 陈雪冰, 黄超;
  • 基金资助:


Concise Synthesis of Quinolinone Derivatives

Chen Xuebinga, Bai Hairuib, Huang Chaob   

  1. a. Key Laboratory of Natural Pharmaceutical and Chemical Biology of Yunnan Province, School of Science, Honghe University, Mengzi 661100;
    b. Engineering Research Center of Biopolymer Functional Materials of Yunnan Province, School of Chemistry and Environment, Yunnan Minzu University, Kunming 650503
  • Received:2016-11-01 Revised:2016-12-27 Published:2017-01-17
  • Contact: 10.6023/cjoc201611003;
  • Supported by:

    Project supported by the National Natural Science Foundation of China (Nos. 21202142, 21662046), the Yunnan Provincal Department of Education Fund (No. 2016ZZX217).

A concise and efficient protocol for the synthesis of novel quinolinone derivatives 4 has been established from a intramolecular cyclization of cyanoacetylenaminones 3, which were synthesized by the regio-selective cyanoacylation reaction of β-enaminones 1 with cyanoacetic acid 2. The reaction was performed in acetonitrile media at 40 ℃, and piperidine as catalyst. As a result, a novel series of quinolinones 4a~4t were obtained with the yields of 82%~95%. The reaction is particularly attractive due to the following advantages of operational simplicity, atom economy, simple starting materials, and easy purification.

Key words: β-enaminones, regionselectivity acylation, intramolecular cyclization, quinolinones