A convenient and efficient approach to 2-arylamino-5-fluoroalkyl-1,3,4-oxadiazoles has been established via heterocyclization of tri- and difluoroacetylated thiosemicarbazides using dicyclohexylcarbodiimide. A heterocyclization performed with selected thiosemicarbazides under basic conditions led to 4-aryl-5-fluoroalkyl-2,4-dihydro-3H-1,2,4-triazole-3-thiones in moderate yields. The starting fluoroacetylated thiosemicarbazides were prepared by fluoroacetylation of benzyloxycarbonyl-protected hydrazine with a corresponding anhydride, followed by hydrogenolytic deprotection and reaction with arylisothiocyanates. Fluoroacetylated semicarbazides were prepared similarly, but all attempts to achieve their heterocyclization were unsuccessful.
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Published in Khimiya Geterotsiklicheskikh Soedinenii, 2016, 52(2), 133–139
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Mlostoń, G., Obijalska, E., Żurawik, A. et al. Efficient synthesis of tri- and difluoroacetyl hydrazides as useful building blocks for non-symmetrically substituted, fluoroalkylated 1,3,4-oxadiazoles. Chem Heterocycl Comp 52, 133–139 (2016). https://doi.org/10.1007/s10593-016-1845-3
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DOI: https://doi.org/10.1007/s10593-016-1845-3