Synthesis of fluorinated N-arylpyrazoles with perfluoro-2-methyl-2-pentene and arylhydrazines

Add time:07/28/2019    Source:sciencedirect.com

Reactions of arylhydrazines (phenyl, 2-nitrophenyl, 4-nitrophenyl, 2,4-dinitrophenyl, pentafluorophenyl, 4-trifluoromethyl-2,3,5,6-tetrafluorophenylhydrazine or 4,4′-dihydrazinooctafluorobiphenyl) with perfluoro-2-methyl-2-pentene in the presence of triethylamine have effectively produced 1-aryl-perfluoro-3-ethyl-4-methylpyrazole and 1-aryl-perfluoro-5-ethyl-4-methylpyrazole in various ratios depending on the reaction conditions and arylhydrazine used. Syn- and anti-aminoimines which might be the intermediates for pyrazoles have been isolated under appropriate conditions. The routes of formation for these products and the role of triethylamine have been discussed. The reaction of perfluoro-2-methyl-2-pentene with phenylhydrazine has been investigated in detail. The structure of 3-fluoro-5-pentafluoroethyl-1-phenyl-4-trifluoromethylpyrazole has been elucidated by X-ray crystallography.

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