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3-Methylidene-2,4-dioxo-4-pentafluorophenylbutanoates in the Synthesis of Heterocycles

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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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Authors and Affiliations

  1. Institute of Organic Synthesis, Ural Division, Russian Academy of Sciences, ul. S. Kovalevskoi/Akademicheskaya 20/22, Yekaterinburg, 620219, Russia

    A. S. Fokin, Ya. V. Burgart, V. I. Saloutin & O. N. Chupakhin

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  1. A. S. Fokin
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  2. Ya. V. Burgart
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  3. V. I. Saloutin
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  4. O. N. Chupakhin
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Dedicated to Full Member of the Russian Academy of Sciences N.S. Zefirov on His 70th Anniversary

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Translated from Zhurnal Organicheskoi Khimii, Vol. 41, No. 9, 2005, pp. 1380–1385.

Original Russian Text Copyright © 2005 by Fokin, Burgart, Saloutin, Chupakhin.

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Fokin, A.S., Burgart, Y.V., Saloutin, V.I. et al. 3-Methylidene-2,4-dioxo-4-pentafluorophenylbutanoates in the Synthesis of Heterocycles. Russ J Org Chem 41, 1354–1358 (2005). https://doi.org/10.1007/s11178-005-0346-0

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  • DOI: https://doi.org/10.1007/s11178-005-0346-0

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