Journal
MOLECULES
Volume 26, Issue 18, Pages -Publisher
MDPI
DOI: 10.3390/molecules26185579
Keywords
annulation reactions; [1; 4]thiazino[2; 3; 4-ij]quinolin-4-ium derivatives; 8-quinolinesulfenyl chloride; heterocycles; 4-pentenoic acid; 5-hexenoic acid; allyl halides
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A novel family of [1,4]thiazino[2,3,4-ij]quinolin-4-ium derivatives was synthesized through annulation reactions, showing regioselective reactions with different substrates. The compounds demonstrated high antibacterial activity against various bacteria.
A novel family of [1,4]thiazino[2,3,4-ij]quinolin-4-ium derivatives was synthesized by annulation reactions of 8-quinolinesulfenyl chloride with unsaturated heteroatom and heterocyclic compounds. It was found that the reactions with 4-pentenoic and 5-hexenoic acids, allyl chloride and bromide, allyl cyanate and vinyl heterocyclic compounds (N-vinyl pyrrolidin-2-one and 1-vinylimidazole) proceeded in a regioselective mode but with the opposite regiochemistry. The reactions with vinyl heterocyclic compounds included electrophilic addition of the sulfur atom of 8-quinolinesulfenyl chloride to the beta-carbon atom of the vinyl group. In the case of other substrates, the annulation proceeded with the attachment of the sulfur atom to the alpha-carbon atom of the vinyl group. The antibacterial activity of novel water-soluble compounds against Enterococcus durans, Bacillus subtilis and Escherichia coli was evaluated. Compounds with high antibacterial activity were found.
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