Abstract
(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. The corresponding resonances were assigned on the basis of the standard 1D and gradient selected 2D NMR experiments (1H-1H gs-COSY, 1H-13C gs-HSQC, 1H-13C gs-HMBC) with 1H-15N gs-HMBC as a practical tool to determine 15N NMR chemical shifts at the natural abundance level of 15N isotope.
Highlights
1,4-Disubstituted 1,2,3-triazole is considered to be a suitable structural part of compounds that could be of interest from the point of view of various research areas
There was offered the idea of the removal of protecting acetyl group and the oxidative conversion of obtained primary alcohols as well as starting triazolylmethanols to the corresponding 1,2,3-triazole-4-carbaldehydes and 1,2,3-triazole-4-carboxylic acids
We tried processing with a methanolic solution of sodium methoxide, in parallel with ester methanolysis, undesirable nucleophilic quinoline-2,4-dione ring opening and successive reactions took place resulting in mixtures, from which only corresponding N-substituted anthranilic acids and eventually their methyl esters were isolated after neutralization with diluted hydrochloric acid
Summary
1,4-Disubstituted 1,2,3-triazole is considered to be a suitable structural part of compounds that could be of interest from the point of view of various research areas. Since still more reports on the 4-hydroxy-quinolin-2-one derivatives, in which hydrogen atom of hydroxyl group was replaced with various substituents comprising 1,2,3-triazole pattern, have been published.[22,23,24,25,26,27,28,29] Some of these substances have been found to show some acetylcholine receptors binding affinity.[22] Recently we have reported an utilization of the above mentioned 3-(1H-1,2,3-triazol1-yl)quinoline-2,4(1H,3H)-diones unsubstituted on the nitrogen atom of the quinolone moiety for the synthesis of bis(1,2,3-triazole) functionalized quinoline-2,4-diones.[30] In frame of that study,[30] in place of starting materials were used, among others, derivatives of (1H-1,2,3-triazol-4-yl) methanol, in which hydroxyl group was protected by acetylation and their structure was subsequently modified. Some known 1-substituted 1,2,3-triazol-4-carboxylic acids have antibacterial effect against Staphylococcus aureus.[33]
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