Preparation of compounds including quinoline-2,4-dione and 1,2,3-triazolyl moieties in molecules.

What is it about?

(1-(2,4-Dioxo-1,2,3,4-tetrahydroquinolin-3-yl)-1H-1,2,3-triazol-4-yl)methyl acetates substituted on nitrogen atom of quinolinedione moiety with propargyl group or (1-substituted 1H-1,2,3-triazol-4-yl)methyl group, which are available from the appropriate 3-(4-hydroxymethyl-1H-1,2,3-triazol-1-yl)quinoline-2,4(1H,3H)-diones unsubstituted on quinolone nitrogen atom by the previously described procedures, were deacetylated by acidic ethanolysis. Thus obtained primary alcohols, as well as those aforenamed unsubstituted on quinolone nitrogen atom, were oxidized to aldehydes on the one hand with pyridinium chlorochromate (PCC), on the other hand with manganese dioxide, and to carboxylic acids using Jones reagent in acetone. The structures of all prepared compounds were confirmed by 1H, 13C and 15N NMR spectroscopy

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Why is it important?

In terms of biological effects, 1,2,3-triazole-4-carbaldehydes are particularly interesting. For example, a series of them has been found to prove tuberculostatic effect. Some (1H-1,2,3-triazol-4-yl)methanols exhibit cytotoxic activity. Some known 1-substituted 1,2,3-triazol-4-carboxylic acids have antibacterial effect against Staphylococcus aureus.

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