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Synthesis 2024; 56(12): 1881-1890
DOI: 10.1055/a-2254-0712
DOI: 10.1055/a-2254-0712
paper
A Simple and Efficient Approach for the Synthesis of Aryl-3-(trifluoromethyl)-1H-1,2,4-triazol-5(4H)-one Derivatives
The authors would like to thank the Office of Graduate Studies of Vali-e-Asr University of Rafsanjan for their partial financial support and cooperation. The authors are also especially grateful to the Iranian National Science Foundation (INSF) for funding this work as part of postdoctoral research (4012539).
Abstract
In this work, a series of 4-aryl-3-(trifluoromethyl)-1H-1,2,4-triazol-5(4H)-one derivatives is synthesized through nucleophilic intramolecular cyclization reactions of ethyl 2-(2,2,2-trifluoro-1-(arylimino)ethyl)hydrazine-1-carboxylate intermediates, which are themselves prepared in high yields via reactions of ethyl chloroformate and N-aryl-2,2,2-trifluoroacetimidoyl chloride derivatives. Some of the merits of the reported procedure are an operationally simple and concise method, the ready availability of starting materials, excellent product yields, no formation of harmful by-products and easy purification of the products.
Key words
4-aryl-3-(trifluoromethyl)-1H-1,2,4-triazol-5(4H)-ones - ethyl chloroformate - ethyl 2-(2,2,2-trifluoro-1-(arylimino)ethyl)hydrazine-1-carboxylates - trifluoroacetimidoyl chlorides - trifluoroacetimidohydrazides - N-heterocyclesSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/a-2254-0712.
- Supporting Information
Publication History
Received: 30 October 2023
Accepted after revision: 25 January 2024
Accepted Manuscript online:
25 January 2024
Article published online:
27 February 2024
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