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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 41, 2011 - Issue 13
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Original Articles

Synthesis of New Perfluoroalkylated 1,3,4-Oxadiazoles and 1,2,4-Triazoles Starting from 2-(Perfluoroalkyl)ethane Thiols

, &
Pages 1990-1998 | Received 28 Feb 2010, Published online: 02 May 2011
 

Abstract

5-{[2-(Perfluoroalkyl)ethylthio]methyl}-1,3,4-oxadiazole-2-thiones 4a, b and 4-amino-5-{[2-(perfluoroalkyl)ethylthio]methyl}-4H-1,2,4-triazole-3-thiones 5a, b have been prepared from 2-(perfluoroalkyl)ethane thiols 1a, b through a multistep reaction sequence. Compounds 4a, b were further reacted with aryloxysulfonylisocyanates to give the corresponding 5-{[2-(perfluoroalkyl)ethylthio]methyl}-N-(aryloxysulfonyl)-2-thioxo-1,3,4-oxadiazole-3(2H)-carboxamide 6a–d. The new products were obtained in good to moderate yields, and their structures were established on the basis of their infrared, NMR, and mass spectral data.

ACKNOWLEDGMENTS

We are grateful to the Tunisian Ministry of High Education and Scientific Research and Technology for financial support (LR99ES14) of this research and to Dr. M. A. Sanhoury, MRSC of the Department of Chemistry, Faculty of Sciences of Tunis, for technical assistance and helpful discussions.

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