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Method for preparing 5-acylamino-1,4,5-trisubstituted 1,2,3-triazole in water phase and biological medium

A biological medium and three-substitution technology, applied in organic chemistry and other fields, to achieve high reaction efficiency and mild reaction conditions

Inactive Publication Date: 2018-03-23
DALIAN UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, there is no report on the transition metal-catalyzed alkyne amine-azido cycloaddition reaction in aqueous phase.

Method used

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  • Method for preparing 5-acylamino-1,4,5-trisubstituted 1,2,3-triazole in water phase and biological medium
  • Method for preparing 5-acylamino-1,4,5-trisubstituted 1,2,3-triazole in water phase and biological medium

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0020] Example 1: Preparation of 1-benzyl-4-phenyl-5-(pyrazolin 2-one group)-1H-1,2,3-triazole

[0021] Under air, 3-phenylethynyl-pyrazolin 2-one (0.2 mmol, 37.4 mg) was added to water (2 mL), followed by benzyl azide (0.3 mmol, 40.2 mg) and [Ir( COD)Cl] 2 (0.005mmol, 3.3mg), the reaction mixture was stirred at room temperature, and reacted for 12h. After the reaction, it was extracted with ethyl acetate, the solvent was selected to be dry, and the product was separated by column chromatography to obtain 54.4mg of a yellow solid product with a yield of 85%.

Embodiment 2

[0022] Example 2: Preparation of 1-benzyl-4-p-methoxyphenyl-5-(pyrazolin 2-one)-1H-1,2,3-triazole

[0023] 3-p-Methoxyphenylethynyl-pyrazolin 2-one (0.2 mmol, 43.4 mg) was added to water (2 mL) followed by benzyl azide (0.3 mmol, 40.2 mg) under air and [Ir(COD)Cl] 2 (0.005mmol, 3.3mg), the reaction mixture was stirred at room temperature, and reacted for 12h. After the reaction, it was extracted with ethyl acetate, the solvent was selected to be dry, and the product was separated by column chromatography to obtain 60.9mg of a yellow liquid product with a yield of 87%.

Embodiment 3

[0024] Example 3: Preparation of 1-benzyl-4-p-chlorophenyl-5-(pyrazolin 2-one)-1H-1,2,3-triazole

[0025] Under air, 3-p-chlorophenylethynyl-pyrazolin 2-one (0.2 mmol, 44.2 mg) was added to water (2 mL), followed by benzyl azide (0.3 mmol, 40.2 mg) and [ Ir(COD)Cl] 2 (0.005mmol, 3.3mg), the reaction mixture was stirred at room temperature, and reacted for 12h. After the reaction, it was extracted with ethyl acetate, the solvent was selected to be dry, and the white solid product was separated by column chromatography to obtain 56.7mg, with a yield of 80%.

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Abstract

The invention belongs to the technical field of organic synthesis, and relates to a method for preparing 5-acylamino-1,4,5-trisubstituted 1,2,3-triazole in a water phase and a biological medium. The 5-acylamino-1,4,5-trisubstituted 1,2,3-triazole is prepared by catalyzing an alkynyl amine compound and nitrine in presence of a 1,5-cyclooctadiene iridium chloride dimer catalyst in a solvent. The preparation method of the 5-acylamino-1,4,5-trisubstituted 1,2,3-triazole product adopts mild reaction conditions, and the product yield is not lower than 80%. The preparation method has the advantages of mild reaction conditions, environment friendliness and high reaction efficiency, and has potential biological application value; the prepared 5-acylamino-1,4,5-trisubstituted 1,2,3-triazole compoundhas potential physiological activity.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis and relates to a preparation method of novel 5-amido-1,4,5-trisubstituted 1,2,3-triazole in aqueous phase and biological medium. Background technique [0002] The alkyne-azido cycloaddition reaction is one of the most important methods for the preparation of 1,2,3-triazoles. In recent years, a series of documents or patents have reported the preparation methods of 1,2,3-triazole compounds. [0003] In 2001, the Medal research group and the Sharpless research group respectively reported the copper-catalyzed terminal alkyne-azide cycloaddition reaction (J.Org.Chem., 2002, 67, 3057 and Angew.Chem.Int.Ed., 2002, 41, 2596). Subsequently, this reaction has been extensively studied and paid attention to. However, there is no report on the transition metal-catalyzed alkyne amine-azide cycloaddition reaction in aqueous phase. How to realize the alkyne amine-azido cycloaddition reaction in aqu...

Claims

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Application Information

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IPC IPC(8): C07D249/04C07D249/06
CPCC07D249/04C07D249/06
Inventor 宋汪泽郑楠郑玉斌
Owner DALIAN UNIV OF TECH
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