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

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

Cite this article

Xixi Zheng, Yunyun Liu, Jie-Ping Wan. Metal-Free Synthesis of 1,2,3-Triazoles in Pure Water via the Enamine Modified Annulation Reactions with Tosyl Azide[J]. Chinese Journal of Organic Chemistry, 2021, 41(7): 2700-2706.

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