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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.
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Submitted on : Tuesday, January 5, 2016 - 5:53:18 PM
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Nada Marquise, Floris Chevallier, Ekhlas Nassar, Michel Frédérich, Allison Ledoux, et al.. Substituted Azafluorenones: Access from Dihalogeno Diaryl Ketones by Palladium-Catalyzed Auto-Tandem Processes and Evaluation of their Antibacterial, Antifungal, Antimalarial and Antiproliferative Activities. Tetrahedron, Elsevier, 2016, 72 (6), pp.825-836. ⟨10.1016/j.tet.2015.12.050⟩. ⟨hal-01251206⟩

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