Chinese Journal of Organic Chemistry ›› 2021, Vol. 41 ›› Issue (7): 2700-2706.DOI: 10.6023/cjoc202104053 Previous Articles     Next Articles

ARTICLES

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*()   

  1. 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 发布日期:2021-05-25
  • 通讯作者: 万结平
  • 基金资助:
    国家自然科学基金(21861019); 江西省自然科学基金(20202ACBL203006)

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()   

  1. College of Chemistry and Chemical Engineering, Jiangxi Normal University, Nanchang 330022
  • Received:2021-04-26 Revised:2021-05-10 Published:2021-05-25
  • Contact: Jie-Ping Wan
  • Supported by:
    National Natural Science Foundation of China(21861019); Natural Science Foundation of Jiangxi Province(20202ACBL203006)

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