串联型氮杂-迈克尔加成/分子内亲核取代反应构建1,3-硅杂四氢吡啶环  

Synthesis of 1,3-Sila-tetrahydropyridine By Using A Tandem aza-Michael Reaction Intramolecular Nucleophilic Substitution

作　　者：李林洁[1] 范昱 马昌 高璐[1] 宋振雷[1] LI Lin-jie;FAN Yu;MA Chang;GAO Lu;SONG Zhen-lei(West China School of Pharmacy, Sichuan University, Chengdu 610041, China)

机构地区：[1]四川大学华西药学院,四川成都610041

出　　处：《合成化学》2022年第2期77-83,共7页Chinese Journal of Synthetic Chemistry

基　　金：国家自然科学基金优青项目(21622202)。

摘　　要：开发了2-硅-1,3-碘代对甲苯磺酰胺试剂。该试剂在碳酸钾促进下,可与炔酯以及烷基、芳基和杂环取代的炔酮发生串联型氮杂-迈克尔加成/分子内亲核取代反应,以中等至优秀的收率(40%~90%)得到相应的1,3-硅杂四氢吡啶产物。通过该方法,合成了16个结构新颖的1,3-硅杂四氢吡啶,其结构经^(1)H NMR,^(13)C NMR和HR-MS(ESI)表征。We have developed 2-sila-1,3-iodo-p-toluenesulfonamide as a useful reagent for the synthesis of 1,3-sila-tetrahydropyridines.The reaction proceeds via a potassium carbonate-promoted tandem aza-Michael reaction/intramolecular nucleophilic substitution process,and tolerates with alkynyl esters,alkyl-aryl-heteroaryl-substituted ynones.We have synthesized sixteen structurally diverse 1,3-sila-tetrahydropyridines in moderate to excellent yield(40%-90%),all of which were confirmed by ^(1)H NMR,^(13)C NMR and HR-MS(ESI).

关 键 词：硅杂四氢吡啶 炔酮 氮杂-迈克尔加成 分子内亲核取代 串联反应 合成 

分 类 号：O621.25[理学—有机化学]