Chinese Journal of Organic Chemistry ›› 2020, Vol. 40 ›› Issue (12): 4298-4304.DOI: 10.6023/cjoc202005087 Previous Articles     Next Articles


刘新明a, 李路a, 晋李成a, 赵金灿b, 华远照c, 王敏灿c, 刘澜涛a,c   

  1. a 商丘师范学院化学化工学院 河南商丘 476000;
    b 河北大学化学与环境科学学院 河北保定 071002;
    c 郑州大学化学学院 郑州 450001
  • 收稿日期:2020-05-29 修回日期:2020-07-02 发布日期:2020-07-23
  • 通讯作者: 刘澜涛, 赵金灿;
  • 基金资助:

Oxidative Halocyclization of N-Allylarylamides with KX/Oxone System: Green Synthesis of 5-Halomethyl-2-Oxazolines

Liu Xinminga, Li Lua, Jin Lichenga, Zhao Jincanb, Hua Yuanzhaoc, Wang Mincanc, Liu Lantaoa,c   

  1. a College of Chemistry and Chemical Engineering, Shangqiu Normal University, Shangqiu, Henan 476000;
    b College of Chemistry & Environmental Science, Hebei University, Baoding, Hebei 071002;
    c College of Chemistry, Zhengzhou University, Zhengzhou 450001
  • Received:2020-05-29 Revised:2020-07-02 Published:2020-07-23
  • Supported by:
    Project supported by the National Natural Science Foundation of China (No. 21572126), the Program of Science and Technology Innovation Talents of Henan Province (No. 2018JQ0011), the Natural Science Foundation of Hebei Province (No. B2019201415), and the Fundamental Research Funds for the Midwest Universities Comprehensive Strength Promotion Project (No. 521000981026).

With inexpensive potassium halide (KX) as halogen source, and oxone as oxidant, a series of allylamides underwent halocyclization reaction and generated 5-halomethyl-2-oxazolines in good to excellent isolated yields under mild conditions. The protocol showed attractive advanced features including low cost of halogen source, absence of organic byproduct, and resultant environmental-friendly nature. In addition, various useful derivatives could be expected by proper nucleophilic substitution reactions.

Key words: oxone, halocyclization, oxazolines