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CC BY-NC-ND 4.0 · Synthesis 2023; 55(08): 1221-1226
DOI: 10.1055/s-0042-1751401
DOI: 10.1055/s-0042-1751401
paper
An Efficient Catalyst-Free Direct Approach to 5-Polyfluoroalkyl-1,2,4-triazole-3-thiones
This study was partially supported by the Ministry of Education and Science of Ukraine (State Budget Projects 0119U100232 and 0120U100431).
Abstract
An easy to handle high-efficient approach to 5-polyfluoroalkyl-1,2,4-triazole-3-thiones (11 examples, up to 91% yield) is reported. The tautomerism of thione and thiol forms for the obtained products is discussed. A one step procedure for 6,6-dimethyl-3-(trifluoromethyl)-5,6-dihydro[1,3]thiazolo[2,3-c][1,2,4]triazole formation from trifluoroacetic acid and 4-methallylthiosemicarbazide has been developed. The structures of the products were unambiguously determined by complex NMR investigation and by single crystal X-ray diffraction.
Key words
thiosemicarbazide - perfluorocarboxylic acid - 1,2,4-triazol-3-thione - fluoroalkyl - [1,3]thiazolo[2,3-c][1,2,4]triazole - electrophilic cyclizationSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0042-1751401.
- Supporting Information
Publication History
Received: 02 January 2022
Accepted after revision: 28 November 2022
Article published online:
05 January 2023
© 2023. The Author(s). This is an open access article published by Thieme under the terms of the Creative Commons Attribution-NonDerivative-NonCommercial-License, permitting copying and reproduction so long as the original work is given appropriate credit. Contents may not be used for commercial purposes or adapted, remixed, transformed or built upon. (https://creativecommons.org/licenses/by-nc-nd/4.0/)
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