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2022 , Vol. 42 >Issue 9: 2898 - 2905

DOI: https://doi.org/10.6023/cjoc202204024

研究论文

碱催化下单-1-取代-1,2,3-三唑选择性氢-氘交换反应研究

  • 李冬英 ,
  • 邱闪光 ,
  • 陈昱学 ,
  • 赵艳梅 ,
  • 魏云龙 ,
  • 吴禄勇 ,
  • 陈文豪
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  • 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

收稿日期: 2022-04-10

  修回日期: 2022-05-18

  网络出版日期: 2022-06-09

基金资助

海南省自然科学基金(219MS044); 国家自然科学基金(22167013); 海南师范大学化学与化工学院研究生创新基金(Hgs202006)

收起

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

  • Dongying Li ,
  • Shanguang Qiu ,
  • Yuxue Chen ,
  • Yanmei Zhao ,
  • Yunlong Wei ,
  • Luyong Wu ,
  • Wenhao Chen
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  • Key Laboratory of Tropical Medicinal Resources Chemistry of Ministry of Education, College of Chemistry and Chemical Engineering, Hainan Normal University, Haikou 571158
* Corresponding author. E-mail:

Received date: 2022-04-10

  Revised date: 2022-05-18

  Online published: 2022-06-09

Supported by

Hainan Provincial Natural Science Foundation(219MS044); National Natural Science Foundation of China(22167013); Graduate Student Innovation Research Project of College of Chemistry and Chemical Engineering, Hainan Normal University(Hgs202006)

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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-BuOK, t-BuONa或Cs2CO3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.

关键词： 氢-氘交换; 标记化合物; 单-1-取代-1,2,3-三唑; 碱催化

本文引用格式

李冬英 , 邱闪光 , 陈昱学 , 赵艳梅 , 魏云龙 , 吴禄勇 , 陈文豪 . 碱催化下单-1-取代-1,2,3-三唑选择性氢-氘交换反应研究[J]. 有机化学, 2022 , 42(9) : 2898 -2905 . DOI: 10.6023/cjoc202204024

Abstract

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-BuOK, t-BuONa or Cs2CO3 in 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.

Key words： H/D exchange; labeling compounds; mono-1-substituted 1,2,3-triazoles; base-catalysis

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