Alternative Functionalization of 2‐(3, 4‐Dihalophenyl)‐4H‐chromen‐4‐ones via Metal‐Free Nucleophilic Aromatic Fluorine Substitution and Palladium‐Catalyzed Cross‐Coupling Reactions. Issue 33 (2nd September 2022)

• Record Type: Journal Article
• Authors: Shcherbakov, Konstantin V.; Panova, Mariya A.; Burgart, Yanina V.; Sinegubova, Ekaterina O.; Orshanskaya, Iana R.; Zarubaev, Vladimir V.; Gerasimova, Natalia A.; Evstigneeva, Natalia P.; Saloutin, Victor I.
• Is Part Of: ChemistrySelect. Volume 7:Issue 33(2022)
• Page Start: n/a
• Page End: n/a
• Publication Date: 2022-09-02
• Subjects: Dihalo-substituted flavones -- Nucleophilic substitution -- C−C coupling -- Azolyl- and aryl-substituted flavones -- Antifungal agents; Chemistry -- Periodicals; 540.5
• DOI: 10.1002/slct.202201775
• Languages: English
• ISSNs: 2365-6549

Abstract

Abstract: Alternative pathways for the functionalization of 2‐(3‐bromo‐4‐fluorophenyl)‐ and 2‐(3, 4‐difluorophenyl)‐4 H ‐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‐(1 H ‐azol‐1‐yl) phenyl]‐4 H ‐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. Abstract : Two alternative pathways for the functionalization of 2‐(3, 4‐dihalophenyl)‐4 H ‐chromen‐4‐ones under conditions of metal‐free base‐promoted nucleophilic aromatic substitution and palladium‐catalyzed Suzuki‐Miyaura cross‐coupling and possibility of implementing both synthetic techniques have been studied. Presence of a triazole fragment in the synthesized flavones has a positive anti‐influenza effect, while an imidazole moiety promoted a significant increase in fungistatic activity.