Alternative Functionalization of 2‐(3,4‐Dihalophenyl)‐4H‐chromen‐4‐ones via Metal‐Free Nucleophilic Aromatic Fluorine Substitution and Palladium‐Catalyzed Cross‐Coupling Reactions

Abstract

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.