A kind of synthetic method of nh-1,2,3-triazole compound

A technology of triazole compound and synthesis method, which is applied in the direction of organic chemistry, can solve the problems of high reaction temperature, many synthesis steps, and long reaction time, and achieve the effects of mild reaction conditions, high reaction efficiency, and short reaction time

Active Publication Date: 2016-06-01
SHANGHAI PUKANG PHARMA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The limitation of this synthetic route is that the alkyne bond must be connected with a strong electron-withdrawing group, and the synthesis of this substrate is difficult
[0008] In 2004, Kim's group[23] reported that 2-pyridylacetylene and TMSN 3 Reflux in DMF to synthesize 4-(2-pyridyl)-NH-1,2,3-triazole with a yield of 38% to 71%. This method has a high reaction temperature and low yield
[0016] In summary, the above methods for synthesizing NH-1,2,3-triazole compounds all have many steps, long reaction time, high reaction temperature, and high yield. However, it has disadvantages such as low efficiency, few suitable substrates or difficult synthesis, high toxicity or poor safety of raw materials, and expensive catalysts.

Method used

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  • A kind of synthetic method of nh-1,2,3-triazole compound
  • A kind of synthetic method of nh-1,2,3-triazole compound
  • A kind of synthetic method of nh-1,2,3-triazole compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0040] Synthesis of 4-phenyl-1H-1,2,3-triazole:

[0041] The reaction formula is:

[0042]

[0043] The specific steps are: add 0.3mmol p-toluenesulfonyl azide, 0.33mmol phenylacetylene, 0.03mmol copper acetate, 0.015mmol o-aminophenol, and 3mL acetonitrile into a 25mL round-bottomed flask, and stir the reaction at 25°C for 20 minutes. Add 1mL of distilled water, then the reaction solution was magnetically stirred and refluxed at 80°C for 12 hours. After the reaction was completed, it was cooled to room temperature, and the reaction solution was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous sodium sulfate, and then reduced pressure The solvent was evaporated to obtain the crude product, which was separated and purified by column chromatography using ethyl acetate / petroleum ether=1:2 (v / v) as the eluent to obtain the desired product. The product is a white solid with a yield of 90%. The proton nuclear magnetic resonan...

Embodiment 2

[0045] Synthesis of 4-phenyl-1H-1,2,3-triazole:

[0046] The reaction formula is:

[0047]

[0048] Add 3mmol p-toluenesulfonyl azide, 3mmol phenylacetylene, 0.3mmol copper acetate, 0.15mmol hydroquinone, 30mL acetonitrile into a 100mL round-bottomed flask, stir and react under magnetic force at 30°C for 30 minutes, then add 5mL distilled water, then The reaction solution was magnetically stirred and refluxed at 130°C for 1 hour. After the reaction was completed, it was cooled to room temperature, and the reaction solution was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure to obtain The crude product was separated and purified by column chromatography using ethyl acetate / petroleum ether=1:2 (v / v) as the eluent to obtain the desired product. The product is a white solid with a yield of 88%. The proton nuclear magnetic resonance spectrogram result of ...

Embodiment 3

[0050] Synthesis of 4-p-tolyl-1H-1,2,3-triazole:

[0051] The reaction formula is:

[0052]

[0053] The specific steps are: add 0.6mmol p-toluenesulfonyl azide, 1.2mmol p-toluene acetylene, 0.06mmol cuprous acetate, 0.03mmol p-aminophenol, 6mL tetrahydrofuran into a 50mL round bottom flask, and stir the reaction under magnetic force at 25°C After 30 minutes, 2 mL of distilled water was added, and then the reaction solution was magnetically stirred and refluxed for 20 hours at 90°C. After the reaction was completed, it was cooled to room temperature, and the reaction solution was extracted with ethyl acetate. The organic layer was washed with saturated saline, and dried over anhydrous sodium sulfate. Finally, the solvent was evaporated under reduced pressure to obtain the crude product, which was separated and purified by column chromatography using ethyl acetate / petroleum ether=1:2 (v / v) as the eluent to obtain the desired product. The product is a brown-red solid with a ...

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Abstract

The invention relates to a synthetic method of NH-1, 2, 3-triazole compound, and the method comprises the following steps: carrying out a magnetic stirring reaction of p-toluenesulfonyl azide, aryl acetylene, catalyst, ligand and solvent at 20-30 DEG C for 10-60 min, adding a few amount of water into the reaction solution and heating, carrying out a magnetic stirring reaction at 80-130 DEG C for 1-20 hours, after reacting, cooling the reaction solution to room temperature, extracting, washing organic layer, drying, distilling with reduced pressure to remove the solvent and obtaining a crude product, separating by a column chromatography and obtaining the products. The p-toluenesulfonyl azide and aryl acetylene which are cheap and easily available are used as substrates, after a catalyst effect, the NH-1, 2, 3-triazole compound can be effectively synthesized. Compared with the prior art, the invention has the advantages of mild reaction condition, short reaction time, good safety, simple operation, high reaction efficiency and cheap catalyst, and the method has a latent application value.

Description

technical field [0001] The invention relates to a method for synthesizing NH-1,2,3-triazole compounds, belonging to the technical field of organic and pharmaceutical synthesis. Background technique [0002] NH-1,2,3-triazole compounds are a class of nitrogen-containing heterocyclic compounds with important physiological activities, widely used in preservatives, pesticides, optical materials, dyes, HIV-1 inhibitors, antibiotics, selective β 3 - Adrenal antagonists, antivirals and anticonvulsants. The activity test shows that the 4-aryl-NH-1,2,3-triazole compound can be used as an inhibitor of human methionine aminopeptidase (hMetAP2). Recent literature reports that some 4-aryl-NH-1,2,3-triazole compounds also have indoleamine 2,3-dioxygenase (IDO) inhibitory activity and are potential IDO inhibitors, so NH -1,2,3-triazole compounds can be used to treat various major human diseases such as cancer, Alzheimer's disease, and cataract, and have broad market prospects. [0003] ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D249/06
Inventor 匡春香杨青李新涓子汪迅李勇刚
Owner SHANGHAI PUKANG PHARMA
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