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2021 , Vol. 41 >Issue 7: 2700 - 2706

DOI: https://doi.org/10.6023/cjoc202104053

研究论文

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

  • 郑茜茜 ,
  • 刘云云 ,
  • 万结平
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  • 江西师范大学 化学化工学院 南昌 330022

收稿日期: 2021-04-26

  修回日期: 2021-05-10

  网络出版日期: 2021-05-25

基金资助

国家自然科学基金(21861019); 江西省自然科学基金(20202ACBL203006)

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

  • Xixi Zheng ,
  • Yunyun Liu ,
  • Jie-Ping Wan
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  • College of Chemistry and Chemical Engineering, Jiangxi Normal University, Nanchang 330022
* Corresponding author. E-mail:

Received date: 2021-04-26

  Revised date: 2021-05-10

  Online published: 2021-05-25

Supported by

National Natural Science Foundation of China(21861019); Natural Science Foundation of Jiangxi Province(20202ACBL203006)

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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.

关键词： 烯胺; 环化反应; 无金属; 纯水介质; 1,2,3-三氮唑

本文引用格式

郑茜茜 , 刘云云 , 万结平 . 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[J]. 有机化学, 2021 , 41(7) : 2700 -2706 . DOI: 10.6023/cjoc202104053

Abstract

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 ofN-alkyl sulfonamides via the reactions of correspondingN-alkyl enaminoesters and tosyl azide has been observed under identical conditions.

Key words： enamine; annulation; metal-free; pure water medium; 1,2,3-triazole

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