Process for preparing 2-triazole-quinoline-4-carboxylic acid compounds
A technology for carboxylic acid compounds and triazoles, applied in the field of synthesizing 2-triazole-quinoline-4-carboxylic acid compounds and 2-triazole-quinoline-4-carboxylic acid compounds, can solve the problem of yield Low cost, long time, cumbersome steps and other problems, to achieve the effect of high yield, simple operation and good application value
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Embodiment 1
[0037] 2-[1-benzyl-5-methyl-1 H- 1,2,3-triazol-4-yl]-4-quinolinecarboxylic acids
[0038]
[0039] In a 25mL small flask, add 2.0mmol benzyl bromide, 2.3mmolNaN 3 Solid, 5 mL dimethylsulfoxide. The reaction solution was heated to 70°C under stirring, and after 10-12 hours of reaction, 1.5 mmol of acetylacetone was added to the mixed solution, followed by the addition of 0.2 equivalents of diethylamine catalyst, 70 o Reflux and stir in an oil bath of C, track with a TLC plate during the reaction, add 1.0 mmol isatin to the flask after 24 hours, and add 1 mL of 8M potassium hydroxide at the same time, raise the reaction temperature to 80 ° C, stir and reflux for 2 ~4 hours. After the reaction is complete, cool to room temperature, add 2 mL of water to the mixture, and adjust the pH to 6~7 with acetic acid solution. After precipitation occurs, filter the filter residue, wash with absolute ethanol for 2 to 3 times, and finally wash with anhydrous Na 2 SO 4 Dry, filter, ...
Embodiment 2
[0041] 2-[1-(4-Bromo-benzyl)-5-methyl-1 H- 1,2,3-triazol-4-yl]-4-quinolinecarboxylic acids
[0042]
[0043] In a 25 mL small flask was added 2.0 mmol 14-bromo-benzyl bromide, 2.3 mmol NaN 3 Solid, 5 mL dimethylsulfoxide. The reaction solution was heated to 70°C under stirring, and after 10-12 hours of reaction, 1.5 mmol of acetylacetone was added to the mixed solution, followed by the addition of 0.2 equivalents of diethylamine catalyst, 70 o Reflux and stir in an oil bath of C, track with a TLC plate during the reaction, add 1.0 mmol isatin to the flask after 24 hours, and add 1 mL of 8M potassium hydroxide at the same time, raise the reaction temperature to 80 ° C, stir and reflux for 2 ~4 hours. After the reaction is complete, cool to room temperature, add 2 mL of water to the mixture, and adjust the pH to 6~7 with acetic acid solution. After precipitation occurs, filter the filter residue, wash with absolute ethanol for 2 to 3 times, and finally wash with anhydro...
Embodiment 3
[0045] 2-[1-(4-Methoxy-benzyl)-5-methyl-1 H- 1,2,3-triazol-4-yl]-4-quinolinecarboxylic acids
[0046]
[0047] In a 25 mL small flask was added 2.5 mmol 14-methoxy-benzyl bromide, 2.8 mmol NaN 3 Solid, 5 mL of N,N-dimethylformamide. The reaction solution was heated to 70°C under stirring, and after 10-12 hours of reaction, 1.5 mmol of acetylacetone was added to the mixed solution, followed by the addition of 0.2 equivalents of diethylamine catalyst, 70 o Reflux and stir in an oil bath of C, track with a TLC plate during the reaction, add 1.0 mmol isatin to the flask after 24 hours, and add 1 mL of 8M sodium hydroxide at the same time, raise the reaction temperature to 80 ° C, stir and reflux for 2 ~4 hours. After the reaction is complete, cool to room temperature, add 2 mL of water to the mixture, and adjust the pH to 6~7 with acetic acid solution. After precipitation occurs, filter the filter residue, wash with absolute ethanol for 2 to 3 times, and finally wash with...
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