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

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.