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Reaction of polyfluorinated chalcones with guanidine

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Abstract

Reactions of polyfluorinated chalcones with guanidine in the presence of bases are accompanied by elimination of the polyfluorophenyl group. 3-(Pentafluorophenyl)-1-phenylprop-2-en-1-one and its derivatives reacted with guanidine under basic conditions to give 4-phenylpyrimidin-2-amine, polyfluorobenzenes, and Michael adducts, 3-(2-amino-4-phenylpyrimidin-5-yl)-3-(4-R-2,3,5,6-tetrafluorophenyl)-1-phenylpropan-1-ones. 1-(Pentafluorophenyl)-3-phenylprop-2-en-1-one and 1,3-bis(pentafluorophenyl)prop-2-en-1-one were converted into cinnamic acid derivatives whose reaction with guanidine afforded 2-amino-6-aryl-5,6-dihydropyrimidin-4(1H)-ones.

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Authors and Affiliations

  1. Vorozhtsov Novosibirsk Institute of Organic Chemistry, Siberian Branch, Russian Academy of Sciences, pr. Akademika Lavrent’eva 9, Novosibirsk, 630090, Russia

    E. A. Borodina, N. A. Orlova, Yu. V. Gatilov & O. I. Sal’nikova

  2. Novosibirsk State University, ul. Pirogova 2, Novosibirsk, 630090, Russia

    Yu. V. Gatilov

Authors
  1. E. A. Borodina
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  2. N. A. Orlova
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  3. Yu. V. Gatilov
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  4. O. I. Sal’nikova
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Correspondence to N. A. Orlova.

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Original Russian Text © E.A. Borodina, N.A. Orlova, Yu.V. Gatilov, O.I. Sal’nikova, 2015, published in Zhurnal Organicheskoi Khimii, 2015, Vol. 51, No. 12, pp. 1778–1785.

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Borodina, E.A., Orlova, N.A., Gatilov, Y.V. et al. Reaction of polyfluorinated chalcones with guanidine. Russ J Org Chem 51, 1745–1752 (2015). https://doi.org/10.1134/S1070428015120143

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  • DOI: https://doi.org/10.1134/S1070428015120143

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