No abstract

The possibility of functionalization of 2-(polyfluorophenyl)-4H-chromen-4-ones, with them having different numbers of fluorine atoms, with 1,2,4-triazole or imidazole under conditions of base-promoted nucleophilic aromatic substitution has been shown. A high selectivity of mono-substitution was found with the use of an azole (1.5 equiv.)/NaOBut(1.5 equiv.)/MeCN system. The structural features of fluorinated mono(azolyl)-substituted flavones in crystals were established using XRD analysis. The ability of penta- and tetrafluoroflavones to form persubstituted products with triazole under azole (6 equiv.)/NaOBut(6 equiv.)/DMF conditions was found in contrast to similar transformations with imidazole. On the basis of mono(azolyl)-containing polyfluoroflavones in reactions with triazole and pyrazole, polynuclear hybrid compounds containing various azole fragments were obtained. For poly(pyrazolyl)-substituted flavones, green emission in the solid state under UV-irradiation was found, and for some derivatives, weak fungistatic activity was found.

Alternative pathways for the functionalization of 2‐(3‐bromo‐4‐fluorophenyl)‐ and 2‐(3,4‐difluorophenyl)‐4H‐chromen‐4‐ones have been studied under conditions of metal‐free base‐promoted nucleophilic aromatic substitution and palladium‐catalyzed Suzuki‐Miyaura cross‐coupling reaction. The possibility of implementing these two synthetic techniques is shown by the example of obtaining 2‐[3‐aryl‐4‐(1H‐azol‐1‐yl) phenyl]‐4H‐chromen‐4‐ones. Evaluation of the antimicrobial effect of the synthesized azolyl‐substituted flavones was carried out. Compounds with moderate anti‐influenza, anti‐gonococcal and high fungistatic activity were found.