羟基取代乙二胺衍生物与醛反应化学选择性合成取代苯并噁嗪和咪唑啉（英文）  

Chemoselective Synthesis of Substituted Benzoxazines and Imidazolidines by Reactions of Hydroxyl Substituted Ethylenediamine Derivatives with Aldehydes

作　　者：唐子龙 汪明 姚园 谭经照 代宁宁 李新兴 彭丽芬 焦银春 Tang Zilong;Wang Ming;Yao Yuan;Tan Jingzhao;Dai Ningning;Li Xinxing;Peng Lifen;Jiao Yinchun(Key Laboratory of Theoretical Organic Chemistry and Functional Molecular,Ministry of Education,Hunan University of Science and Technology,Xiangtan 411201;Hunan Provincial Key Laboratory of Controllable Preparation and Functional Application of Fine Polymers,School of Chemistry and Chemical Engineering,Hunan University of Science and Technology,Xiangtan 411201)

机构地区：[1]湖南科技大学理论有机化学与功能分子教育部重点实验室,湘潭411201 [2]湖南科技大学化学化工学院精细聚合物可控制备及功能应用湖南省重点实验室,湘潭411201

出　　处：《有机化学》2019年第3期800-810,共11页Chinese Journal of Organic Chemistry

基　　金：Project supported by the National Natural Science Foundation of China(Nos.21877034,21372070);the Scientific Research Fund of Hunan Provincial Education Department(No.17A066)~~

摘　　要：在La(OTf)3的催化作用下,羟基取代乙二胺衍生物与醛通过环化反应,高化学选择性、高效地合成多官能团取代的1,3-咪唑啉和3,1-苯并噁嗪类化合物.脂肪醛和芳香醛都适用于该反应体系.探索了可能的反应机理,O原子和N原子的亲核性对反应的化学选择性起着非常重要的作用.该方法的优点是只需调节羟基取代乙二胺分子中亚甲基的位置,就可以高化学选择性地合成1,3-咪唑啉或3,1-苯并噁嗪类化合物.Lewis acid La(OTf)3-catalyzed chemoselective cyclization of hydroxyl substituted ethylenediamine derivatives with aldehydes has been described for the first time, which provides efficient access to diversely functionalized 1,3-imidazolidines and 3,1-benzoxazines in generally good yields only by adjusting the position of the methylene group within hydroxyl substituted ethylenediamines. The reaction is suitable to aromatic aldehydes and aliphatic ones. Plausible mechanisms are also proposed to explain the observed reaction modes, wherein the nucleophilicity of nitrogen and oxygen atoms plays an important role in controlling the chemoselectivity.

关 键 词：羟基取代乙二胺 1 3-咪唑啉 3 1-苯并噁嗪 化学选择性 合成 

分 类 号：O621.251[理学—有机化学]