Chin. J. Org. Chem. ›› 2018, Vol. 38 ›› Issue (12): 3381-3385.DOI: 10.6023/cjoc201807003 Previous Articles     Next Articles



闫溢哲a,b, 李政a, 崔畅a, 刘延奇a   

  1. a 郑州轻工业学院食品与生物工程学院 郑州 450000;
    b 食品生产与安全河南省协同创新中心 郑州 450000
  • 收稿日期:2018-07-01 修回日期:2018-07-12 发布日期:2018-08-22
  • 通讯作者: 闫溢哲, 刘延奇;
  • 基金资助:


Synthesis of 2,3,5,6-Tetrasubstituted Pyridines via Copper-Catalyzed Domino Oxidative Annulation of 1,3-Dicarbonyl Compounds with Methanol and Ammonium Acetate

Yan Yizhea,b, Li Zhenga, Cui Changa, Liu Yanqia   

  1. a School of Food and Biological Engineering, Zhengzhou University of Light Industry, Zhengzhou 450000;
    b Collaborative Innovation Center of Food Production and Safety, Henan 450000
  • Received:2018-07-01 Revised:2018-07-12 Published:2018-08-22
  • Contact: 10.6023/cjoc201807003;
  • Supported by:

    Project supported by the National Natural Science Foundation of China (No. 21502177), the Scientific and Technological Breakthrough Plan of Henan Province (No. 182102310903), the Doctoral Research Foundation of Zhengzhou University of Light Industry (No. 2014BSJJ032), and the Grants Program of Youth Backbone Teachers Training Object of Zhengzhou University of Light Industry.

A copper-catalyzed oxidative formal cycloaddition of 1,3-dicarbonyl compounds, methanol and ammonium acetate was first demonstrated, affording symmetrical 2,3,5,6-tetrasubstituted pyridines in moderate to excellent yields. Methanol was employed as the carbon synthon as well as the reaction solvent. The preliminary mechanistic studies revealed that the reaction underwent a radical pathway and the C(sp3)-H bond cleavage of methanol was the rate-determining step. This method is operationally simple and environmentally friendly.

Key words: copper, oxidative annulation, pyridine, methanol