碳酸铯催化吡唑与α,β-不饱和酮的氮杂Michael反应有机化学.pdfVIP

DOI: 10.6023/cjoc201406051 研究论文 有机化学 Chinese Journal of Organic Chemistry ARTICLE 碳酸铯催化吡唑与α,β-不饱和酮的氮杂Michael 反应 杨靖亚*,a 马 奔a 周红艳b 占宝华a 李 政a (a 西北师范大学化学化工学院 兰州 730070) (b 甘肃农业大学理学院 兰州 730070) 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% Cs CO 存在下, 于 1,4-二氧 2 3 六环中回流反应 7～12 h, 以 86%～95%的产率得到 21 种 β-(N 1-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. 关键词 Michael 加成; 含氮杂环; α,β-不饱和酮; 催化; 碳酸铯 Cesium Carbonate Catalyzed Aza-Michael Addition of Pyrazole to α,β-Unsaturated Ketones Yang, Jingya*,a Ma, Bena Zhou, Hongyanb Zhan, Baohuaa Li, Zhenga (a College of Chemistry and Chemical Engineering, Northwest Normal University, Lanzhou 730070) (b College of Science, Gansu Agricultural University, Lanzhou 730070) Abstract A Cs CO -catalyzed aza-Michael reaction of pyrazole to α,β-unsaturated ketones has been developed. With 5 2 3 mol% Cs CO as catalyst, a series of β-N 1-pyrazoly ketones were achieved in 86%～95% yields after 7～12 h in refluxing 2 3 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 fa