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Method for preparing 2-triazole-quinoline-4-carboxylic acid compound

A carboxylic acid compound and triazole technology are applied in the field of 2-triazole-quinoline-4-carboxylic acid compound and synthesis of 2-triazole-quinoline-4-carboxylic acid compound, which can solve the problem of yield low, long time, cumbersome steps and other problems, to achieve the effect of high yield, simple operation, good application value

Inactive Publication Date: 2014-08-20
GUANGXI NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

A method for synthesizing triazole-quinoline-carboxylic acid compounds has been reported (Russian Journal of General Chemistry, 2009, Vol. 79, No. 2, pp. 309–314), the method is as follows: The first step is to synthesize phenyl azide by adding sodium azide to the aniline compound under hydrochloric acid and sodium nitrite; the second step is to use it and acetylacetone in sodium methoxide as a catalyst and methanol as a solvent after obtaining azide Triazole is obtained under the conditions; the third step is to use the triazole to react with isatin under ethanol / water solution of potassium hydroxide to obtain the final triazole-quinoline-4-carboxylic acid compound, and the preparation method is Synthesized in 3 steps, the yield is low, the time is long, and the steps are cumbersome

Method used

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  • Method for preparing 2-triazole-quinoline-4-carboxylic acid compound
  • Method for preparing 2-triazole-quinoline-4-carboxylic acid compound
  • Method for preparing 2-triazole-quinoline-4-carboxylic acid compound

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Embodiment 1

[0038] 2-[1-benzyl-5-methyl-1 H- 1,2,3-triazol-4-yl]-4-quinolinecarboxylic acids

[0039]

[0040] In a 25 mL small flask add 2.0 mmol benzyl bromide, 2.3 mmol NaN 3 Solid, 5 mL DMSO. The reaction solution was heated to 70°C under stirring, and after 10-12 hours of reaction, 1.5 mmol 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 2~4 hours. After the reaction was 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, remove the ...

Embodiment 2

[0042] 2-[1-(4-Bromo-benzyl)-5-methyl-1 H- 1,2,3-triazol-4-yl]-4-quinolinecarboxylic acids

[0043]

[0044] In a 25 mL small flask add 2.0 mmol 4-bromo-benzyl bromide, 2.3 mmol NaN 3 Solid, 5 mL DMSO. The reaction solution was heated to 70°C under stirring, and after 10-12 hours of reaction, 1.5 mmol 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 2~4 hours. After the reaction was 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, filt...

Embodiment 3

[0046] 2-[1-(4-Methoxy-benzyl)-5-methyl-1 H- 1,2,3-triazol-4-yl]-4-quinolinecarboxylic acids

[0047]

[0048] In a 25 mL small flask add 2.5 mmol 4-methoxy-benzyl bromide, 2.8 mmol NaN 3 Solid, 5 mL N,N-dimethylformamide. The reaction solution was heated to 70°C under stirring, and after 10-12 hours of reaction, 1.5 mmol 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 2~4 hours. After the reaction was 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 N...

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Abstract

The invention discloses a method for preparing a 2-triazole-quinoline-4-carboxylic acid compound. The method comprises the steps of using benzyl halide, sodium azide, a 1-3-dicarbonyl compound and isatin as raw materials, and performing one-pot synthesis under the catalysis of diethylamine and strong alkali to obtain a 1,2,3-triazole substituted quinoline-4-carboxylic acid compound. The method is easily-available in raw material, simple in operation and high in yield, and has good application prospects.

Description

technical field [0001] The present invention relates to triazole-quinoline compounds, specifically quinoline carboxylic acid compounds, more specifically 2-triazole-quinoline-4-carboxylic acid compounds, especially the synthesis of 2-triazole-quinoline-4 - Method of carboxylic acid compound. Background technique [0002] 1,2,3-Triazole compounds have unique chemical properties and have broad application prospects in many fields such as pesticides, medicine and materials. Especially in medical applications, such as β -Inhibition of lactamase, anti-HIV, antibacterial, anti-allergic, anti-tumor, anti-viral, anti-epileptic, analgesic and control of potassium metabolism related to cardiovascular diseases and other properties. Li Wenjie once reported that triazoles have inhibitory activity on the proliferation of breast cancer cells overexpressing HER2, and found that the inhibitory activity of these compounds on HER2 phosphorylation in the cells was significantly related to the...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D401/04
CPCC07D401/04
Inventor 温祖煌潘英明王恒山
Owner GUANGXI NORMAL UNIV
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