串联式三组分反应构建取代吡唑杂环  

Sequential Three-Component Reactions for the Assembly of Functionalized Pyrazoles

作　　者：李玉峰[1] 黄佳维 顾嘉超 黄浩[1] 钮长盛 马鸿飞[1] 

机构地区：[1]南京工业大学化学与分子工程学院,南京211816

出　　处：《有机化学》2016年第3期520-526,共7页Chinese Journal of Organic Chemistry

摘　　要：建立一种串联三组分反应构建取代吡唑杂环的方法.以肼和醛为原料在二氯乙烷中反应先生成腙3,直接加入丙炔酸甲酯(4),在氯化亚铜催化下快速生成Michael加成产物5.该中间体以化学量的三氯化铁氧化发生环合反应,获得高收率的吡唑环衍生物6.各步反应中间体不必分离,脂肪肼、芳香肼以及芳香醛对该反应具有良好适应性.A sequential three-component reaction for the assembly of functionalized pyrazoles is described. Aldehydes are treated with hydrazines in dichloroethane to generate hydrazones（3）, which in situ take place aza-Michael reaction quickly with methyl propiolate（4） catalyzed by Cu Cl to give Michael adducts（5）. Subsequent oxidation of 5 with stoichiometric Fe Cl3 provides substituted pyrazoles with high to excellent yields. The intermediates of the synthetic method are not necessary to isolate. Aliphatic hydrazines, aromatic hydrazines as well as aromatic aldehydes are well adaptable to the reaction.

关 键 词：肼 醛 丙炔酸甲酯 吡唑 三组分反应 

分 类 号：O626[理学—有机化学]