Chinese Journal of Organic Chemistry ›› 2020, Vol. 40 ›› Issue (9): 2871-2878.DOI: 10.6023/cjoc202003047 Previous Articles     Next Articles


房观念, 由君, 喻艳超, 荆军凯, 刘波, 武文菊   

  1. 哈尔滨理工大学化学与环境工程学院 黑龙江省绿色化工技术重点实验室 哈尔滨 150040
  • 收稿日期:2020-03-19 修回日期:2020-05-22 发布日期:2020-06-20
  • 通讯作者: 由君, 武文菊;
  • 基金资助:

Study on the Reaction of Acetone Cyanohydrin with 3,5-Dimethyl-N-α,β-unsaturated Acyl Pyrazole

Fang Guannian, You Jun, Yu Yanchao, Jing Junkai, Liu Bo, Wu Wenju   

  1. Key Laboratory of Green Chemical Engineering and Technology of Heilongjiang Province, College of Chemical and Environmental Engineering, Harbin University of Science and Technology, Harbin 150040
  • Received:2020-03-19 Revised:2020-05-22 Published:2020-06-20
  • Supported by:
    Project supported by the National Natural Science Foundation of China (No. 21908034), and the Natural Science Foundation of Heilongjiang Province (No. LH2019B010).

Cyano compounds are a class of organic compounds with great value. Two different kinds of reactions have been reported using acetone cyanohydrin as reagent and substituted 3,5-dimethyl-N-α,β-unsaturated acyl pyrazole as substrate. The reaction pathway depends on the basic catalysts used when aromatic substituted 3,5-dimethyl-N-α,β-unsaturated acyl pyrazole was used as the substrate. Michael addition reaction occurred in the presence of MgBu2 with the product yield up to 95%, while alcoholysis reaction of amide occurred in the presence of 1,1,3,3-tetramethylguanidine (TMG), producing β-substituted phenyl cyanoacrylates with 84% yield. However, fatty substituted 3, 5-dimethyl-N-α,β-unsaturated acyl pyrazole and acetone cyanohydrin underwent Michael addition reaction in the presence of MgBu2 or TMG, the product yield was up to 99%. The possible reaction mechanism when using different basic catalysts was discussed.

Key words: acetone cyanohydrin, 3,5-dimethyl-N-α,β-unsaturated acyl pyrazole, Michael addition, β-substituted phenyl cyanoacrylate