Substituted Azafluorenones: Access from Dihalogeno Diaryl Ketones by Palladium-Catalyzed Auto-Tandem Processes and Evaluation of their Antibacterial, Antifungal, Antimalarial and Antiproliferative Activities - Université de Rennes Accéder directement au contenu
Article Dans Une Revue Tetrahedron Année : 2016

Substituted Azafluorenones: Access from Dihalogeno Diaryl Ketones by Palladium-Catalyzed Auto-Tandem Processes and Evaluation of their Antibacterial, Antifungal, Antimalarial and Antiproliferative Activities

Résumé

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.

Domaines

Chimie
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Dates et versions

hal-01251206 , version 1 (05-01-2016)

Identifiants

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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, 2016, 72 (6), pp.825-836. ⟨10.1016/j.tet.2015.12.050⟩. ⟨hal-01251206⟩
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