碱催化下单-1-取代-1,2,3-三唑选择性氢-氘交换反应研究  

Research for the Reaction of Base-Catalyzed Selective Hydrogen-Deuterium Exchange in Mono-1-substituted 1,2,3-Triazoles

作　　者：李冬英 邱闪光 陈昱学[1] 赵艳梅 魏云龙 吴禄勇[1] 陈文豪[1] Dongying Li;Shanguang Qiu;Yuxue Chen;Yanmei Zhao;Yunlong Wei;Luyong Wu;Wenhao Chen(Key Laboratory of Tropical Medicinal Resources Chemistry of Ministry of Education,College of Chemistry and Chemical Engineering,Hainan Normal University,Haikou 571158)

机构地区：[1]海南师范大学化学与化工学院热带药用资源化学教育部重点实验室,海口571158

出　　处：《有机化学》2022年第9期2898-2905,共8页Chinese Journal of Organic Chemistry

基　　金：海南省自然科学基金(No.219MS044);国家自然科学基金(No.22167013);海南师范大学化学与化工学院研究生创新基金(No.Hgs202006)资助项目。

摘　　要：探索了一种碱催化下单-1-取代的1,2,3-三唑的选择性氢-氘交换反应.以t-Bu OK,t-Bu ONa或Cs_(2)CO_(3)作为碱,单-1-取代的1,2,3-三唑在二甲基亚砜(DMSO)-d6溶液中可以选择性地实现C5位置的氘代.在相应的反应条件下, 4,5-双氘代1,2,3-三唑在相应的反应条件下进行氘-氢交换,可以选择性地实现C5位置的去氘代过程,从而实现C4氘代的1,2,3-三唑化合物的合成.同时,三唑环辅助下的苯环上的氢-氘交换过程也被观察到.An effective and selective deuteration of mono-1-substituted 1,2,3-triazoles using base-catalyzed hydrogen-deuterium exchange is proposed. The H/D exchange was selectively conducted at C5 position of 1,2,3-triazoles with catalytic amount of t-Bu OK, t-Bu ONa or CsCOin dimethyl sulfoxide DMSO-d6. From corresponding 1,2,3-triazoles via H/D exchange process, 5-deutero and 4-deutero mono-1-substituted 1,2,3-triazoles were given from corresponding 1,2,3-triazoles respectively. In addition, the triazole-induced deuteration on phenyl ring was observed.

关 键 词：氢-氘交换 标记化合物 单-1-取代-1 2 3-三唑 碱催化 

分 类 号：O621.251[理学—有机化学]