碳酸铯催化吡唑与α,β-不饱和酮的氮杂Michael反应  

Cesium Carbonate Catalyzed Aza-Michael Addition of Pyrazole to α,β-Unsaturated Ketones

作　　者：杨靖亚[1] 马奔[1] 周红艳[2] 占宝华[1] 李政[1] 

机构地区：[1]西北师范大学化学化工学院,兰州730070 [2]甘肃农业大学理学院,兰州730070

出　　处：《有机化学》2015年第1期121-128,共8页Chinese Journal of Organic Chemistry

基　　金：国家自然科学基金(Nos.21362034;21162026);高等学校博士学科点专项科研基金(No.20136203120005);甘肃省自然科学基金(No.1107RJZ189);西北师范大学青年教师科研能力提升计划(No.NWNU-LKQN-11-15);甘肃农业大学科技创新基金(No.GAU-CX1115)资助项目~~

摘　　要：发展了一种碳酸铯催化吡唑与α,β-不饱和酮的氮杂Michael反应新方法.在5 mol%Cs2CO3存在下,于1,4-二氧六环中回流反应7~12 h,以86%~95%的产率得到21种β-（N1-吡唑基）酮.此法对芳香类和脂肪类α,β-不饱和酮均适用良好,易实现克级放大.产物可容易地转化为相应的γ-氨基醇.发展的方法同样适用于吡唑与丙烯酸甲酯和硝基苯乙烯的氮杂Michael反应.A Cs2CO3-catalyzed aza-Michael reaction of pyrazole to aft-unsaturated ketones has been developed. With 5 mol% Cs2CO3 as catalyst, a series of β-Nl-pyrazoly ketones were achieved in 86%~95% yields after 7~12 h in refluxing dioxane. Both aromatic and aliphatic α,β-unsaturated ketones as well as methacrylate and nitrostyrene are well tolerated. Broad scope of substrate and easily scale up make this protocol really practical. Furthermore, the product could be facilely trans- formed into corresponding γ-amino alcohol.

关 键 词：MICHAEL加成 含氮杂环 Α Β-不饱和酮 催化 碳酸铯 

分 类 号：O621.25[理学—有机化学]