一种结构新颖的中氮茚衍生物的合成新方法  

A New and Efficient Methodology for the Synthesis of Novel Indolizine Derivatives

作　　者：叶青青[1] YE Qing-qing(Department of Medicine,Chuzhou City Vocation College,Chuzhou 239000,China)

机构地区：[1]滁州城市职业学院医学系,安徽滁州239000

出　　处：《安徽师范大学学报（自然科学版）》2021年第6期545-550,共6页Journal of Anhui Normal University(Natural Science)

基　　金：安徽省教育厅自然科学基金重点项目(KJ2020A1003,KJ2020A1004);滁州城市职业学院自然科学研究项目(2020zk03).

摘　　要：以吡啶作为碱和反应底物,利用其与溴代苯乙酮和叠氮基肉桂酸酯的三组分串联反应发展了一种合成结构新颖的1,2,3-三取代中氮茚衍生物的新方法。利用溴代苯乙酮与吡啶形成的氮叶立德作为亲核试剂和1,3-偶极子前体,经由1,3-偶极环加成反应构建中氮茚骨架。各种叠氮基肉桂酸烷基酯和苄基酯均能很好的适用于该反应,产率为54%~79%,吡啶上连有取代基时该反应不能发生,所有产物结构均经^(1)H NMR,^(13)C NMR和HR-MS表征。最后根据实验结果提出了一种可能的反应机理。A novel and efficient base-promoted three-component reactions of pyridine with azido cinnamic esters and 2-bromoacetophenones for the synthesis of novel 1,2,3-trisubstituted indolizine derivatives in good to high yields has been developed.Construction of indolizine skeleton via 1,3-dipolar cycloaddition using pyridine and 2-bromoacetophenones derived N-ylides as nucleophiles and 1,3-dipole precursors.Various alkyl and benzyl azido cinnamic esters were applied to this reaction well and generated the corresponding indolizine derivatives in 54%-79%yields.The structures of all compounds were characterized by ^(1)H NMR,^(13)C NMR and HR-MS.A proposed mechanism was described.

关 键 词：1 3-偶极环加成 叠氮基肉桂酸酯 中氮茚 三组分反应 溴代苯乙酮 

分 类 号：O626[理学—有机化学]