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Reaction of polyfluorinated chalcones with guanidine
Authors:E A Borodina  N A Orlova  Yu V Gatilov  O I Sal’nikova
Institution:1.Vorozhtsov Novosibirsk Institute of Organic Chemistry, Siberian Branch,Russian Academy of Sciences,Novosibirsk,Russia;2.Novosibirsk State University,Novosibirsk,Russia
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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