3-Methylidene-2,4-dioxo-4-pentafluorophenylbutanoates in the Synthesis of Heterocycles |
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Authors: | A S Fokin Ya V Burgart V I Saloutin O N Chupakhin |
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Institution: | (1) Institute of Organic Synthesis, Ural Division, Russian Academy of Sciences, ul. S. Kovalevskoi/Akademicheskaya 20/22, Yekaterinburg, 620219, Russia |
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Abstract: | 3-Ethoxy- and 3-arylaminomethylidene-2,4-dioxo-4-pentafluorophenylbutanoates undergo cyclization by the action of hydrazine hydrate and phenylhydrazine to give ethyl 4-pentafluorobenzoylpyrazole-5-carboxylates. The reaction of 3-ethoxymethylidene-2,4-dioxo-4-pentafluorophenylbutanoate with o-phenylene-diamine leads to formation of 3-2-(2-aminophenylamino)-1-pentafluorobenzoylethenyl]-1,2-dihydroquinoxa-lin-2-one. 3-Arylaminomethylidene-2,4-dioxo-4-pentafluorophenylbutanoates react with o-phenylenediamine to afford 3-(1-aryl-5,6,7,8-tetrafluoro-4-oxo-1,4-dihydroquinolin-3-yl)-1,2-dihydroquinoxalin-2-ones and/or 3-(2-arylamino-1-pentafluorobenzoylethenyl)-1,2-dihydroquinoxalin-2-ones. |
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