Substituted azafluorenones: Access from dihalogeno diaryl ketones by palladium-catalyzed auto-tandem processes and evaluation of their antibacterial, antifungal, antimalarial and antiproliferative activities

Abstract

Substituted azafluorenones were synthesized from dihalogeno diaryl ketones under palladium catalysis by combining, in auto-tandem processes, Suzuki coupling and intramolecular arylation reactions. Different dihalogenated diaryl ketones, prepared by sequential deprotocupration-aroylation, were identified as suitable substrates to this purpose. Conditions were identified to allow successful syntheses of several 6-/7-arylated 4-azafluorenones, 1-substituted 4-azafluorenones, 2-phenyl-3-azafluorenone, and 4-phenyl-3-azafluorenone from 3-(bromobenzoyl)-2-chloropyridines, 3-benzoyl-4-bromo-2-chloropyridines, 4-benzoyl-2,5-dichloropyridine, and 4-benzoyl-2,3-dichloropyridine, respectively. Some of the synthesized compounds exhibit interesting biological properties.