Abstract
By potential-controlled electrochemical reduction, 2-hydroxyamino-1-pentafluorophenylethanol has been converted in the presence of nitrous acid into 1-hydrazino-2-pentafluorophenylethanol, which on heating in dimethylformamide forms 1-amino-4, 5, 6, 7-tetrafluoroindole or 1-amino-4, 5, 6, 7-tetrafluoro-3-hydroxyin hydroxyindoline, depending on the conditions. On being heated with hydrochloric acid, both cyclization products are converted into 5, 6, 7, 8-tetrafluoro-1, 4-dihydrocinnoline, which has been oxidized to 5, 6, 7, 8-tetrafluorocinnoline.
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Petrov, V.P., Barkhash, V.A. Preparation and cyclization of 2-hydrazino-1-pentafluorophenylethanol. Chem Heterocycl Compd 6, 353–356 (1970). https://doi.org/10.1007/BF00471240
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DOI: https://doi.org/10.1007/BF00471240