无金属和氧化剂温和条件下碱促进的烯胺酮碳-碳双键断裂合成NH2-结构脒类化合物  

Base-Promoted,Metal-and Oxidant-Free C=C Bond Cleavage in Enaminones for Ambient Synthesis of NH2-Amidines

作　　者：王国栋 郭艳辉 万结平[1] Wang Guodong;Guo Yanhui;Wan Jieping(College of Chemistry and Chemical Engineering Jiangxi Normal University,Nanchang 330022)

机构地区：[1]江西师范大学化学化工学院,南昌330022

出　　处：《有机化学》2020年第3期645-650,共6页Chinese Journal of Organic Chemistry

基　　金：国家自然科学基金(No.21562025)资助项目。

摘　　要：报道了室温条件下烯胺酮和磺酰叠氮通过碳-碳双键断裂合成N-磺酰基醚类化合物的方法.反应在1,8-二.氮杂双环[5.4.0]十一碳-7-烯(DBU)存在下进行,无需使用任何金属和氧化剂,具有良好的底物适用性.烯胺酮上的15N同位素标记实验证实,磺酰叠氮仅作为产物中的磺酰胺片段供体,同时,该实验也有力地支持反应机理涉及关键的1,2,3-三唑啉中间体的原位形成以及环分解.The C=C double bond cleavage of NH2-functionalized enaminones has been realized at room temperature to provide various N-sulfbnyl amidines by reacting with sulfonyl azides.The reactions take place with good substrate tolerance in the presence of 1,8-Diazabicyclo[5.4.0]undec-7-ene(DBU)without any metal or oxidant reagent.The,5N-labelling experiment on enaminone indicates that the sulfonyl azide component donates solely the sulfonamide fragment,and the reaction mechanism involving a key decomposition of the in situ generated 1,2,3-triazoline intermediate is convictively supported.

关 键 词：烯胺酮 碳-碳双键断裂 无金属 无氧化剂 脒 

分 类 号：O621.25[理学—有机化学]