Abstract
Ethyl 5,6,7,8-tetrafluoro-4-oxo-2-phenyl-4H-chromene-3-carboxylate in reactions with primary amines is characterized by a chromone-coumarin rearrangement affording 3-[amino(phenyl)methylene]-6,7,8-trifluoro-2H-chromene-2,4(3H)-diones, and ethyl 4-oxo-2-phenyl-5,6,7,8-tetrafluoro-4H-chromene-3-carboxylate characteristically adds the amine at the C2 site of the flavone furnishing 3-amino-3-phenyl-2-(2,3,4,5-tetrafluoro-6-hydroxybenzoyl)acrylates which depending on the substituent at the amino group are capable of intramolecular cyclization into 3-[(alkylamino)(phenyl)methylene]-5,6,7,8-tetrafluoro-2H-chromene-2,4(3H)-dione or in the case of benzylamine substituent, into ethyl 1-benzyl-5-hydroxy-4-oxo-2-phenyl-6,7,8-trifluoro-1,4-dihydroquinoline-3-carboxylate. The main process in the reaction of tri- and tetrafluoroflavones with secondary amine (1-methylpiperazine) is the nucleophilic substitution at the C7 of flavone. In the reaction with 1,2-phenylenediamine 3-[(2-aminophenyl)amino]-3-phenyl-2-(2,3,4,5-tetrafluoro-6-hydroxybenzoyl)acrylate was obtained from tetrafluoroflavone and 1H-benzimidazol-2-yl(3,4,5-trifluoro-2-hydroxyphenyl)methanone, from trifluoroflavone.
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References
Heterocyclic Compounds, Elderfield, R.C., Ed., New York: Wiley, 1957.
Comprehensive Organic Chemistry, Barton, D. and Ollis, W.D., Eds., Oxford: Pergamon, 1979, vol. 4.
Budzisz, E., Malecka, M., Lorenz, I.-P., Mayer, P., Kwiecien, R.A., Paneth, P., Krajewska, U., and Rozalski, M., Inorg. Chem., 2006, vol. 45, p. 9688.
Saloutin, V.I., Skryabina, Z.E., Bazyl’, I.T., and Kisil’, S.P., J. Fluor. Chem., 1999, vol. 94, p. 83.
Shcherbakov, K.V., Burgart, Ya.V., and Saloutin, V.I., Fromv. Akad. Nauk, Ser. Khim., 2005, vol. 9, p. 2093.
Bazyl’, I.T., Kisil’, S.P., Burgart, Ya.V., and Saloutin, V.I., J. Fluor. Chem., 2000, vol. 103, p. 3.
Vorozhtsov, N.N., Barkhash, V.A., Prudchenko, A.T., and Khomenko, T.I., Zh. Obchsh. Khim., 1965, vol. 35, p. 1501.
Vorozhtsov, N.N., Brakhash, V.A., Prudchenko, A.T., and Khomenko, T.I., Dokl. Akad/Nauk SSSR, 1965, vol. 164, p. 1046.
Coppola, G.M. and Dodsworth, R.W., Synthesis, 1981, vol. 7, p. 523.
Kisil’, S.P., Burgart, Ya.V., and Saloutin, V.I., Zh. Org. Khim., 2001, vol. 37, p. 1524.
Albert, A. and Serjeant, E., Ionization Constants of Acids and Bases, London: Methuen, 1962.
Shcherbakov, K.V., Burgart, Ya.V., and Saloutin, V.I., Zh. Org. Khim., 2006, vol. 42, p. 1848.
Shcherbakov, K.V., Burgart, Ya.V., Saloutin, V.I., and Chupakhin, O.N., Heterocycles, 2006, vol. 69, p. 319.
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Dedicated to Full Member of the Russian Academy of Sciences I.P. Beletskaya on occasion of her jubilee
Original English Text © K.V. Shcherbakov, Ya.V. Burgart, V. I. Saloutin, 2013, published in Zhurnal Organicheskoi Khimii, 2013, Vol. 49, No. 5, pp. 736–746.
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Shcherbakov, K.V., Burgart, Y.V. & Saloutin, V.I. Features of reactions of polyfluorinated ethyl 4-oxo-2-pnenyl-4H-chromene-3-carboxylates with N-nucleophiles. Russ J Org Chem 49, 719–729 (2013). https://doi.org/10.1134/S1070428013050151
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DOI: https://doi.org/10.1134/S1070428013050151