The Use of Propargylamines to Synthesize Amino-1,2,3-triazoles via Cycloaddition of Azides with Allenamines

Shanguang Qiu; Wenhao Chen; Dongying Li; Yuxue Chen; Yanning Niu; Yi Wu; Yang Lei; Luyong Wu; Wenying He

doi:10.1055/s-0041-1737336

Synthesis, Table of Contents

Synthesis 2022; 54(09): 2175-2184
DOI: 10.1055/s-0041-1737336

paper

The Use of Propargylamines to Synthesize Amino-1,2,3-triazoles via Cycloaddition of Azides with Allenamines

Shanguang Qiu

^aKey Laboratory of Tropical Medicinal Resource Chemistry of Ministry of Education, Hainan Normal University, Haikou, 571158, P. R. of China

,

Wenhao Chen

^aKey Laboratory of Tropical Medicinal Resource Chemistry of Ministry of Education, Hainan Normal University, Haikou, 571158, P. R. of China

,

Dongying Li

^aKey Laboratory of Tropical Medicinal Resource Chemistry of Ministry of Education, Hainan Normal University, Haikou, 571158, P. R. of China

,

Yuxue Chen

^aKey Laboratory of Tropical Medicinal Resource Chemistry of Ministry of Education, Hainan Normal University, Haikou, 571158, P. R. of China

,

Yanning Niu

^bDepartment of Teaching and Research, Nanjing Forestry University, Huaian, 223003, P. R. of China

,

Yi Wu

^aKey Laboratory of Tropical Medicinal Resource Chemistry of Ministry of Education, Hainan Normal University, Haikou, 571158, P. R. of China

,

Yang Lei

^aKey Laboratory of Tropical Medicinal Resource Chemistry of Ministry of Education, Hainan Normal University, Haikou, 571158, P. R. of China

,

Luyong Wu ∗

^aKey Laboratory of Tropical Medicinal Resource Chemistry of Ministry of Education, Hainan Normal University, Haikou, 571158, P. R. of China

,

Wenying He

^aKey Laboratory of Tropical Medicinal Resource Chemistry of Ministry of Education, Hainan Normal University, Haikou, 571158, P. R. of China

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Abstract

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Abstract

A novel reaction of propargylamines with aryl azides is designed for the synthesis of 5-amino-1,2,3-triazoles employing a one-pot strategy. In this process, base-mediated isomerization of propargylamines generates allenamine intermediates, which participate in a cyclization reaction with azides. Optimization of the reaction conditions revealed that t-BuOK as the base and DMF as the solvent gave the best yields. This protocol is expanded to different propargylamines and azides, with the results showing that 3-aryl propargylamines and aryl azides are tolerated to produce the corresponding 1,2,3-triazoles. This procedure provides a simple and efficient method to access a series of 5-amino-1,2,3-triazoles possessing a wide spectrum of functional groups.

Key words

amino-1,2,3-triazoles - propargylamines - allenamines - azides - cycloaddition

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References

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