Palladium-Catalyzed Sonogashira Synthesis of Alkynyl Derivatives of Quinoline-5, 8-Dione
Keywords:Alkynylquinoline-5, 8-diones, Palladium Catalysis, Sonogashira protocol, Terminal alkynes.
The synthesis of various alkynylquinoline-5,8-diones is reported. The intermediate 6,7-dibromoquinoline-5,8-dione was obtained by nitrosation of 8-hydroxyquinoline, followed by reduction and subsequent bromination and oxidation. The coupling reaction of 6,7-dibromoquinoline-5,8-dione with various terminal alkynes via Palladium catalysis gave the alkynylquinoline-5,8-diones in good to excellent yields (50-85% ). The chemical structures of the products were confirmed using spectroscopic methods, which include UV/Visible spectrophotometer, Fourier Transform-Infrared (FT-IR) Spectroscopy, 1H and 13C-NMR Spectroscopy. In vitro antimicrobial activity screening carried out on the compounds against bacterial strains: Escherichia coli 1, Escherichia coli 12, Staphylococcus aureus, Klebsiella pneumonia and Pseudomonas aeroginosa, showed that the synthesized compounds have significant activities (MIC= 0.15-3.20), against the tested organisms. However, compound 5e did not inhibit the growth of Pseudomonas aeroginosa.
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