Chemical Research in Chinese Universities ›› 2015, Vol. 31 ›› Issue (4): 543-548.doi: 10.1007/s40242-015-4480-0

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Solvent-free 1,3-Dipolar Cycloaddition of Azomethine Imines with Terminal Alkynes Promoted by Calcium Fluoride Under the Ball Milling Condition

CHEN Xianglong1, JIA Chunman1,2, CAO Li1, ZHANG Dela1, LIU Shuixiang2, ZHANG Qi1   

  1. 1. Hainan Provincial Key Lab of Fine Chem., Hainan University, Haikou 570228, P. R. China;
    2. Key Study Center of Ministry of Education for Tropical Resources Utilization, Hainan University, Haikou 570228, P. R. China
  • Received:2014-12-12 Revised:2015-05-08 Online:2015-08-01 Published:2015-06-08
  • Contact: JIA Chunman, ZHANG Qi E-mail:jiachunman@hainu.edu.cn;hnfinechem@163.com
  • Supported by:

    Supported by the National Natural Science Foundation of China(Nos.21261008, 21471069), the Special Integration Fund of Industry and Research of Hainan Province, China(No.CXY20130010), the Natural Science Foundation of Hainan Province, China(No.213014) and the International Science and Technology Cooperation Projects of Hainan Province, China(No. KJHZ2014-05).

Abstract:

A convenient and efficient procedure for the synthesis of N,N-bicyclic pyrazolidinone derivatives has been developed via the reaction of azomethine imines with terminal alkynes under the ball milling condition without solvent, which was promoted by calcium fluoride with a catalyst of copper(I) salt. The cyclization reactions exhibited moderate to high yields.

Key words: Ball-milling, 1,3-Dipolar cycloaddition, Click chemistry, Solvent-free reaction