38462-99-6Relevant academic research and scientific papers
Transformations of 3-acyl-4H-polyfluorochromen-4-ones under the action of amino acids and biogenic amines
Shcherbakov, Konstantin V.,Artemyeva, Mariya A.,Burgart, Yanina V.,Evstigneeva, Natalya P.,Gerasimova, Natalya A.,Zilberberg, Natalia V.,Kungurov, Nicolai V.,Saloutin, Victor I.,Chupakhin, Oleg N.
, (2019)
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.
