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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
a   Key Laboratory of Tropical Medicinal Resource Chemistry of Ministry of Education, Hainan Normal University, Haikou, 571158, P. R. of China
,
Wenhao Chen
a   Key Laboratory of Tropical Medicinal Resource Chemistry of Ministry of Education, Hainan Normal University, Haikou, 571158, P. R. of China
,
Dongying Li
a   Key Laboratory of Tropical Medicinal Resource Chemistry of Ministry of Education, Hainan Normal University, Haikou, 571158, P. R. of China
,
Yuxue Chen
a   Key Laboratory of Tropical Medicinal Resource Chemistry of Ministry of Education, Hainan Normal University, Haikou, 571158, P. R. of China
,
Yanning Niu
b   Department of Teaching and Research, Nanjing Forestry University, Huaian, 223003, P. R. of China
,
Yi Wu
a   Key Laboratory of Tropical Medicinal Resource Chemistry of Ministry of Education, Hainan Normal University, Haikou, 571158, P. R. of China
,
Yang Lei
a   Key Laboratory of Tropical Medicinal Resource Chemistry of Ministry of Education, Hainan Normal University, Haikou, 571158, P. R. of China
,
Luyong Wu  ∗
a   Key Laboratory of Tropical Medicinal Resource Chemistry of Ministry of Education, Hainan Normal University, Haikou, 571158, P. R. of China
,
Wenying He
a   Key Laboratory of Tropical Medicinal Resource Chemistry of Ministry of Education, Hainan Normal University, Haikou, 571158, P. R. of China
› InstitutsangabenThis work was supported by the Natural Science Foundation of Hainan Province, China (219MS044) and the National Natural Science Foundation of China (NSFC-21562019).
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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

Supporting Information

    Supporting information for this article is available online at https://doi.org/10.1055/s-0041-1737336.
  • Supporting Information


Publikationsverlauf

Eingereicht: 31. Oktober 2021

Angenommen nach Revision: 09. Dezember 2021

Artikel online veröffentlicht:
01. Februar 2022

© 2022. Thieme. All rights reserved

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