Chinese Journal of Organic Chemistry ›› 2020, Vol. 40 ›› Issue (3): 645-650.DOI: 10.6023/cjoc201912018 Previous Articles     Next Articles


王国栋, 郭艳辉, 万结平   

  1. 江西师范大学化学化工学院 南昌 330022
  • 收稿日期:2019-12-12 修回日期:2019-12-16 发布日期:2019-12-19
  • 通讯作者: 万结平
  • 基金资助:

Base-Promoted, Metal- and Oxidant-Free C=C Bond Cleavage in Enaminones for Ambient Synthesis of NH2-Amidines

Wang Guodong, Guo Yanhui, Wan Jieping   

  1. College of Chemistry and Chemical Engineering, Jiangxi Normal University, Nanchang 330022
  • Received:2019-12-12 Revised:2019-12-16 Published:2019-12-19
  • Supported by:
    Project supported by the National Natural Science Foundation of China (No. 21562025).

The C=C double bond cleavage of NH2-functionalized enaminones has been realized at room temperature to provide various N-sulfonyl amidines by reacting with sulfonyl azides. The reactions take place with good substrate tolerance in the presence of 1,8-Diazabicyclo[5.4.0]undec-7-ene (DBU) without any metal or oxidant reagent. The 15N-labelling experiment on enaminone indicates that the sulfonyl azide component donates solely the sulfonamide fragment, and the reaction mechanism involving a key decomposition of the in situ generated 1,2,3-triazoline intermediate is convictively supported.

Key words: Enaminone, C=C bond cleavage, Metal-free, Oxidant-free, Amidines