关键词: 丙酮氰醇, 3,5-二甲基-N-α,β-不饱和酰基吡唑, Michael加成反应, β-取代苯基丙烯酸氰醇酯

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