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.
Highlights
Many studies have been devoted to the access to azafluorenones, which are compounds of biological interest, for example in relation to their antifungal,[1] antimicrobial,[2] antimalarial,2b,3 and cytotoxic2b,4 activities, or else for their role in the treatment of neurodegenerative disorders.[5]
We have showed that, when applied to the synthesis of 2-chloro diaryl ketones, this method could be combined with direct arylation through C-H bond activation by intramolecular transition metal-catalysis,[11] to afford azafluorenones and related compounds in two steps.[12]
We could achieve the synthesis of substituted azafluorenones by combining cyclization with cross-couplings such as Suzuki[13] and Heck[14] reactions in auto-tandem[15] processes starting from diaryl ketones suitably substituted by two halogeno groups.[16]
Summary
Substituted Azafluorenones: Access from Dihalogeno Diaryl Ketones by Palladium-Catalyzed Auto-Tandem Processes and Evaluation of their Antibacterial, Antifungal, Antimalarial and Antiproliferative Activities.
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