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

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

Publication History

Received: 31 October 2021

Accepted after revision: 09 December 2021

Article published online:
01 February 2022

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