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Method for preparing 1, 2, 3-triazole compound

A technology of azide compounds and compounds, which is applied in the field of catalytic synthesis of organic matter, can solve the problems of not conforming to the concept of green production, high ligand toxicity, large amount of copper application, etc., to overcome the high toxicity of ligands, simple catalytic system, and convenient operation Effect

Inactive Publication Date: 2013-12-25
HENAN NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

There are many catalytic systems for cycloaddition reactions, which can be divided into three types according to the valence state of the catalyst Cu: Cu(0), Cu(I), and Cu(II). Therefore, the study of green synthesis methods has become one of the research hotspots of cycloaddition reactions.

Method used

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  • Method for preparing 1, 2, 3-triazole compound
  • Method for preparing 1, 2, 3-triazole compound
  • Method for preparing 1, 2, 3-triazole compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0010] 4-Benzyloxy-1-phenyl-1H-1,2,3-triazole

[0011]

[0012] Weigh copper acetate (1mmol) and pullulan (10mmol), dissolve completely in water, and add propargyl phenyl ether (100mmol) and phenyl azide (100mmol) at a temperature of 70°C under stirring conditions, Keep the temperature until the end of the reaction. After cooling, a solid precipitates out. Filter and purify to obtain 4-benzyloxy-1-phenyl-1H-1,2,3-triazole.

Embodiment 2

[0014] 4-Benzyloxy-1-p-methoxyphenyl-1H-1,2,3-triazole

[0015]

[0016] Weigh copper acetate (1mmol) and pullulan (1mmol), dissolve completely in water, and add propargyl phenyl ether (100mmol) and p-methoxyphenyl azide at a temperature of 80°C under stirring conditions (100mmol), keep the temperature until the end of the reaction, after cooling, a solid precipitates out, filters and purifies to obtain 4-benzyloxy-1-p-methoxyphenyl-1H-1,2,3-triazol azole.

Embodiment 3

[0018] 4-(4-Chloro-benzyloxy)-1-o-tolyl-1H-1,2,3-triazole

[0019]

[0020] Weigh copper acetate (1mmol) and pullulan (0.1mmol), dissolve completely in water, and add propargyl p-chlorophenyl ether (100mmol) and o-methylphenyl Azide (100mmol), keep the temperature until the end of the reaction, after cooling, solids precipitate out, filter and purify to obtain 4-(4-chloro-benzyloxy)-1-o-tolyl-1H-1,2 ,3-triazole.

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Abstract

The invention discloses a method for preparing a 1, 2, 3-triazole compound. The technical scheme of the invention is as follows: the method for preparing the 1, 2, 3-triazole compound comprises the following steps: (1), weighing copper acetate and Pullulan respectively, fully dissolving the copper acetate and the Pullulan in water, wherein the copper acetate is Cu(OAc)2.H2O; and (2), adding a terminal alkyne compound and an azide compound at 70-100 DEG C while stirring, keeping the temperature till the end of reaction, cooling, separating out a solid, filtering, and purifying to obtain the 1, 2, 3-triazole compound. The using amount of the copper in a catalytic system is reasonable and the defect that a ligand is high in toxicity is overcome, so that the method for preparing the 1, 2, 3-triazole compound is an environment-friendly method.

Description

technical field [0001] The invention belongs to the field of catalytic synthesis of organic matter, and in particular relates to a method for preparing 1,2,3-triazole compounds by using copper acetate / pullulan as a catalytic system. Background technique [0002] Nitrogen-containing heterocyclic compounds have important application value and good biological activity. Many heterocyclic compounds have been developed into new drugs and pesticides. Their synthesis, structure optimization and development research are currently research hotspots in organic chemistry and pesticide chemistry. Azole compounds are the largest clinically used antifungal drugs. Compounds containing 1,2,3-triazoles exhibit diverse biological activities, such as antiallergic, antibacterial, antiviral, antituberculosis, etc. 1,2,3-Triazole is a very attractive group, it has high aromatic stability, is stable to metabolism, the presence of hydrogen bonds leads to good binding ability with biological target ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D249/06C07D403/06
Inventor 丁清杰姜玉钦徐桂清孔端阳张玮玮赵靓琳王栋吴斗灿李伟
Owner HENAN NORMAL UNIV
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