烯胺调控下和对甲苯磺酰叠氮在纯水介质中的无金属环化反应合成1,2,3-三氮唑  

Metal-Free Synthesis of 1,2,3-Triazoles in Pure Water via the Enamine Modified Annulation Reactions with Tosyl Azide

作　　者：郑茜茜 刘云云[1] 万结平[1] Zheng Xixi;Liu Yunyun;Wan Jie-Ping(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》2021年第7期2700-2706,共7页Chinese Journal of Organic Chemistry

基　　金：国家自然科学基金(No.21861019);江西省自然科学基金(No.20202ACBL203006)资助项目.

摘　　要：通过使用简单的Et3N催化容易获得的β-取代NH-烯胺酯和对甲苯磺酰叠氮的反应,高效实现了全取代的1,2,3-三氮唑的合成.在该方法中,水用作反应的唯一介质,以高底物适用性和中等至优秀的产率合成了1,2,3-三氮唑产物.对照实验表明,使用稳定的NH-烯胺作为底物,可能是通过NH基团与水之间的氢键作用实现水介导反应的关键因素.研究还发现,在相同条件下经由相应的N-烷基烯胺酯和对甲苯磺酰叠氮的反应,选择性地生成N-烷基磺酰胺.The synthesis of full substituted 1,2,3-triazoles has been accomplished with high efficiency through the reactions of readily availableβ-substituted NH-enaminoesters and tosyl azide with Et3N catalysis.In this method,water was used as the sole medium for the reactions which provide 1,2,3-triazole products with broad scope and moderate to excellent yield.Control experiments disclose that the employment of stable NH-enamines as substrates is the key factor enabling the water mediated synthesis probably via the hydrogen bonding effect between NH group and water.In addition,the novel and selective production of N-alkyl sulfonamides via the reactions of corresponding N-alkyl enaminoesters and tosyl azide has been observed under identical conditions.

关 键 词：烯胺 环化反应 无金属 纯水介质 1 2 3-三氮唑 

分 类 号：O626[理学—有机化学]