Preparation method of 1,2,3-triazole compound

A technology of azide compounds and compounds, which is applied in the field of polymer/inorganic catalytic synthesis of 1,2,3-triazole compounds, which can solve the problems of shortened reaction time, long reaction time, and easy agglomeration of nano-copper , to achieve the effects of wide application range, simple catalytic system, improved stability and catalytic activity

Active Publication Date: 2014-06-25
YANCHENEG HUIHUANG CHEM
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Metallic copper can also be used to catalyze the Huisgen cycloaddition reaction with metallic copper. Although the reaction under this condition is easy to operate, and the preparation of the catalyst is also simple, the disadvantage is that the reaction time is relatively short when using bulk metallic copper as the catalyst. long
In order to shorten the reaction time, nano-copper can be used as a catalyst, but the disadvantage is that nano-copper is easy to agglomerate during its preparation

Method used

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  • Preparation method of 1,2,3-triazole compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0010] Preparation of brominated pullulan ( Carbohydrate Research 2005, 340, 1403-1406)

[0011] Dissolve 5.0g of pullulan in 160ml of DMF (after dehydration treatment), raise the temperature to 60°C, add 13.00g of lithium bromide after 1 hour and stir vigorously for 1 hour, cool down to room temperature, place in an ice-salt bath to drop below 0°C, A mixed solution of 13.8g NBS and 40ml DMF (treated by distillation under reduced pressure) was added dropwise, stirred for 30 minutes, and the reaction mixture was vigorously stirred at 40°C for 6 hours. The reaction mixture was precipitated with acetone, dissolved with DMF, and precipitated with acetone 4 times to obtain purified bromide Pullulan.

Embodiment 2

[0013] The preparation of pullulan triazole ( doi.org / 10.1016 / j.tetlet.2014.02.108)

[0014] The brominated pullulan polysaccharide prepared in Example 1 is used to prepare pullulan triazole, the steps are as follows: respectively weigh brominated pullulan polysaccharide (12mmol), hydroxypropyne (10mmol), NaN 3 (12mmol), CuSO 4 ·5H 2 O (1mol%) and H 2 O (20 mL) was placed in a 100 mL round-bottomed flask, reacted at room temperature for 3 days, the reaction solution was dialyzed with deionized water for 3 days, and freeze-dried to obtain the purified polymer pullulan triazole.

Embodiment 3

[0016] Preparation of organic azides ( Tetrahedron, 2006, 62(50): 11652; J. Mol. Struct., 2008, 892(1-3): 210)

[0017] Weigh 1.95g (30mmol) NaN 3 Add to a 100mL round bottom flask, add 50mL DMF solution, then add 30mmol chlorinated compound, stir overnight at room temperature, after TLC monitors the reaction is complete, pour the reaction solution into 30mL water, CH 2 Cl 2 3×50mL extraction, combined organic phases, washed 3 times with water, dried over anhydrous sodium sulfate, filtered, spin-dried the solvent, purified by column chromatography, and stored at low temperature for use in subsequent reactions.

[0018] The preparation of other benzyl azide compounds is the same as above.

[0019] Weigh 2.42g (15mmol) of o-trifluoromethylaniline and place it in a 50mL round-bottomed flask, then add 10mL of HCl aqueous solution (v: v = 1:1), stir in an ice-water bath at 0-5°C, and then slowly drop Add NaNO 2 Aqueous solution (1.03g, 15mmol NaNO 2 Dissolved in 6mL ice ...

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Abstract

The invention discloses a preparation method of 1,2,3-triazole compound and belongs to the field of medicament catalyzed synthesis technology. The technical scheme is characterized in that according to the preparation method of the 1,2,3-triazole compound, an end group alkyne compound and organic trinitride are respectively used as raw materials; pullulan triazole/cuprous chloride is used as a catalytic system; water is used as a solvent; the 1,2,3-triazole compound is prepared through mixed stirring reaction under the condition of the room temperature of minus 100 DEG C. According to the preparation method, pullulan polymer cotaining triazole group is applied to Huisgen cycloaddition reaction to be used as an additive to stabilize cuprous ions so that use level of catalyst in the catalytic reaction process is reduced. The catalytic system is mainly subjected to catalytic reaction in water, simple, reliable, high in yield, easy to separate, reusable, green, environmentally friendly, and the like.

Description

technical field [0001] The invention belongs to the technical field of catalytically synthesizing 1,2,3-triazole compounds, and in particular relates to a preparation method for catalytically synthesizing 1,2,3-triazole compounds with polymer / inorganic substances. Background technique [0002] Nitrogen-containing heterocyclic compounds have important application value and good biological activity. Many heterocyclic compounds have been developed as new medicines and pesticides. Their synthesis, structure optimization and development research are the current organic chemistry and pesticide chemistry. research hotspots. As a bioisostere of 1,2,4-triazole, 1,2,3-triazole has high aromatic stability and broad biological activities, such as antibacterial, antifungal, antiviral and antituberculosis wait. The cuprous ion-catalyzed 1,3-dipolar cycloaddition reaction of organic azide and alkyne, also known as the Huisgen-Click reaction discovered by the Sharpless and Meldal research...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D249/06C07D249/04B01J31/30
CPCB01J31/30B01J2231/324C07D249/04C07D249/06
Inventor 张玮玮姜玉钦任保齐时惠敏胡志国
Owner YANCHENEG HUIHUANG CHEM
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