For the first time 6,7,8-trifluoro- and 5,6,7,8-tetrafluorinated 3-benzoylflavones
have been obtained. Their reactions with amino acids and biogenic amines were studied
in comparison with polyfluorinated 3-acetyl-2-methylchromones. For chromones, reactions
at the C-2 are preferred, which lead to the pyrone ring opening to form N-substituted
aminoenketones. Whereas in the case of flavones the main route is the nucleophilic
aromatic substitution of the fluorine atom at the C-7. Flavones and chromones react
in the same way both with dopamine to give aminoenketones, and with proline to form
7-amino-substituted chromen-4-ones. All the reactions of chromen-4-ones are accompanied
by deacylation, except ones of flavones with proline. Among the synthesized aminoenketones,
compounds with high antimycotic and antibacterial action were found.
