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Preparation method of novel 5-acylamino-1,4,5-trisubstituted 1,2,3-triazole

An amide group, tri-substituted technology, applied in the field of organic synthesis, can solve problems such as no public reports on the preparation technology, and achieve the effects of high reaction efficiency and mild reaction conditions

Inactive Publication Date: 2018-02-23
DALIAN UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Although some changes in the regioselectivity of alkyne-azido cycloaddition reactions have been reported, for the preparation of 5-amido-1,4,5-trisubstituted 1,2,3-triazoles The technology has not yet been publicly reported

Method used

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  • Preparation method of novel 5-acylamino-1,4,5-trisubstituted 1,2,3-triazole
  • Preparation method of novel 5-acylamino-1,4,5-trisubstituted 1,2,3-triazole

Examples

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Effect test

Embodiment 1

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

[0021] 3-Phenylethynyl-pyrazolin 2-one (0.2 mmol, 37.4 mg) was dissolved in dichloromethane (2 mL) under air, and 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, 59.5mg of a yellow solid product was obtained by column chromatography, with a yield of 93%.

Embodiment 2

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

[0023] Under air, 3-p-methoxyphenylethynyl-pyrazolin 2-one (0.2mmol, 43.4mg) was dissolved in dichloromethane (2mL), and benzyl azide (0.3mmol, 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, 67.2mg of a yellow liquid product was obtained by column chromatography, with a yield of 96%.

Embodiment 3

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

[0025] 3-p-Chlorophenylethynyl-pyrazolin 2-one (0.2 mmol, 44.2 mg) was dissolved in dichloromethane (2 mL) under air, and benzyl azide (0.3 mmol, 40.2 mg) was added and [Ir(COD)Cl] 2 (0.005mmol, 3.3mg), the reaction mixture was stirred at room temperature, and reacted for 12h. After the reaction, 60.2mg of a white solid product was obtained by column chromatography, with a yield of 85%.

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Abstract

The invention belongs to the technical field of organic synthesis, and relates to a preparation method of novel 5-acylamino-1,4,5-trisubstituted 1,2,3-triazole. The novel 5-acylamino-1,4,5-trisubstituted 1,2,3-triazole is prepared by catalyzing a ynamine compound and nitrine in an organic solvent and under the action of a catalyst of 1,5-cyclooctadiene iridium chloride dipolymer ([Ir(COD)Cl]2). The preparation method of a 5-acylamino-1,4,5-trisubstituted 1,2,3-triazole product is mild in reaction conditions, and the yield of the product is not lower than 70 percent; the preparation method is mild in reaction conditions, is green and is high in reaction efficiency and is more suitable for large-scale production requirements, and a prepared novel 5-acylamino-1,4,5-trisubstituted 1,2,3-triazole compound has potential physiological activity.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis and relates to a preparation method of a novel 5-amido-1,4,5-trisubstituted 1,2,3-triazole. 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, for copper-catalyzed alkyne-azido cycloaddition reactions, 4-amido-1,4,5-trisubstituted 1,2,3-triazoles (Org.Biomol.Chem. 2006, 4, 2679). How to change the regioselectivity of the alkyne-azido cycloaddition reaction ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D403/04C07D249/04
Inventor 宋汪泽郑楠郑玉斌
Owner DALIAN UNIV OF TECH
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