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

Nada Marquise (1) , Floris Chevallier (1) , Ekhlas Nassar (2) , Michel Frédérich (3) , Allison Ledoux (3) , Yury S. Halauko (4) , Oleg A. Ivashkevich (4) , Vadim E. Matulis (5) , Thierry Roisnel (1) , Vincent Dorcet (1) , Florence Mongin (1)

1 ISCR - Institut des Sciences Chimiques de Rennes
2 Department of Chemistry
3 Laboratory of Pharmacognosy
4 UNESCO Chair of Belarusian State University
5 Research Institute for Physico-Chemical Problems

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.

Keywords: antimalarial activity; tandem process; palladium; azafluorenone

Domains: Chemical Sciences

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⟩