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Synthesis 2022; 54(09): 2175-2184
DOI: 10.1055/s-0041-1737336
DOI: 10.1055/s-0041-1737336
paper
The Use of Propargylamines to Synthesize Amino-1,2,3-triazoles via Cycloaddition of Azides with Allenamines
Authors
This work was supported by the Natural Science Foundation of Hainan Province, China (219MS044) and the National Natural Science Foundation of China (NSFC-21562019).
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.
Supporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0041-1737336.
- Supporting Information (PDF)
Publikationsverlauf
Eingereicht: 31. Oktober 2021
Angenommen nach Revision: 09. Dezember 2021
Artikel online veröffentlicht:
01. Februar 2022
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