Citation: Fang Guannian, You Jun, Yu Yanchao, Jing Junkai, Liu Bo, Wu Wenju. Study on the Reaction of Acetone Cyanohydrin with 3, 5-Dimethyl-N-α, β-unsaturated Acyl Pyrazole[J]. Chinese Journal of Organic Chemistry, ;2020, 40(9): 2871-2878. doi: 10.6023/cjoc202003047 shu

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

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

Corresponding author: You Jun, youjunjun@126.com Wu Wenju, wuwenju1017@163.com
Received Date: 19 March 2020
Revised Date: 22 May 2020
Available Online: 19 June 2020
Fund Project: the National Natural Science Foundation of China 21908034the Natural Science Foundation of Heilongjiang Province LH2019B010Project supported by the National Natural Science Foundation of China (No. 21908034), and the Natural Science Foundation of Heilongjiang Province (No. LH2019B010)

Figures(1)

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