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Imidazo[1,2-a]indole compound synthesis method

A technology for synthesizing imidazoles and compounds, which is applied in the field of synthesizing imidazo[1,2-a]indole compounds, can solve problems such as complicated reactions, and achieve the effects of simple reaction steps, mild reaction conditions and easy-to-obtain raw materials

Active Publication Date: 2020-03-10
ZHEJIANG UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Although a variety of methods have been developed to prepare nitrogen-containing heterocyclic compounds, the reaction is relatively complicated, so a general method that uses easy-to-prepare synthons as raw materials and can selectively control substituents still needs to be developed.

Method used

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  • Imidazo[1,2-a]indole compound synthesis method

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Experimental program
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Effect test

Embodiment 1

[0032]

[0033] 2-Bromophenylacetylene (0.5 mmol), p-toluenesulfonyl azide (0.6 mmol) and 2-bromoallylamine (0.5 mmol) were added sequentially to a Schlenk tube. Then 3ml of DMSO was added, stirred, and under the protection of nitrogen, CuI (0.05mmol) was added, and dry triethylamine (0.5mmol) was slowly added dropwise, and the reaction solution was stirred at room temperature for 1h. Add CuI (0.1mmol) to the reaction system, K 2 CO 3 (2mmol) and N,N'-dimethyl-1,2-ethylenediamine (0.3mmol), the reaction temperature was raised from room temperature to 80°C, stirred for 6h, and tracked by thin layer chromatography until the reaction was completed, Cool to room temperature. 4ml of saturated ammonium chloride solution was added to the reaction solution, and extracted three times with 15ml of ethyl acetate, the organic layer was dried over anhydrous sodium sulfate, concentrated and separated by silica gel column chromatography (eluent was petroleum ether: ethyl acetate=6 : 1)...

Embodiment 2

[0036]

[0037] 2-Bromophenylacetylene (0.5 mmol), benzenesulfonyl azide (0.6 mmol) and 2-bromoallylamine (0.5 mmol) were added sequentially to a Schlenk tube. Then 3ml of DMSO was added, stirred, and under the protection of nitrogen, CuI (0.05mmol) was added, and dry triethylamine (0.5mmol) was slowly added dropwise, and the reaction solution was stirred at room temperature for 1h. Add CuI (0.1 mmol) to the reaction system, K 2 CO 3 (2mmol) and N,N'-dimethyl-1,2-ethylenediamine (0.3mmol), the reaction temperature was raised from room temperature to 80°C, stirred for 6h, and tracked by thin layer chromatography until the reaction was completed, Cool to room temperature. 4ml of saturated ammonium chloride solution was added to the reaction solution, and extracted three times with 15ml of ethyl acetate, the organic layer was dried over anhydrous sodium sulfate, concentrated and separated by silica gel column chromatography (eluent was petroleum ether: ethyl acetate=6 : 1),...

Embodiment 3

[0040]

[0041]2-Bromophenylacetylene (0.5 mmol), 2,4,6-trimethylbenzenesulfonyl azide (0.6 mmol) and 2-bromoallylamine (0.5 mmol) were sequentially added to a Schlenk tube. Then 3ml of DMSO was added, stirred, and under the protection of nitrogen, CuI (0.05 mmol) was added, and dry triethylamine (0.5 mmol) was slowly added dropwise, and the reaction solution was stirred at room temperature for 1 h. Add CuI (0.1mmol) to the reaction system, K 2 CO 3 (2mmol) and N,N'-dimethyl-1,2-ethylenediamine (0.3mmol), the reaction temperature was raised from room temperature to 80°C, stirred for 6h, and tracked by thin layer chromatography until the reaction was completed, Cool to room temperature. Add 4ml of saturated ammonium chloride solution to the reaction solution, and extract three times with 15ml of ethyl acetate, the organic layer is dried over anhydrous sodium sulfate, and is separated by silica gel column chromatography after concentration (eluent is sherwood oil: ethyl ace...

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Abstract

The invention discloses an imidazo[1,2-a]indole compound synthesis method, which comprises the following steps: under water-free and oxygen-free conditions, mixing a compound represented by a formula(I), a compound represented by a formula (II), 2-bromoallylamine and a solvent, adding a catalyst A, adding triethylamine in a dropwise manner, stirring at a room temperature for 0.5-3 hours, adding acatalyst B, an alkaline substance and a ligand into the reaction system, heating to 60-90 DEG C, reacting for 5-8 hours, and carrying out post-treatment to obtain the imidazo[1,2-a]indole compound represented by the formula (III). According to the invention, the method is safe and environment-friendly, and does not generate waste gas and wastewater; the raw materials are easy to obtain, the substrate adaptability is good, and aromatization of various substituents can be realized; reaction conditions are mild; reaction steps are simple; and the method is a new route for synthesizing imidazo[1,2-a]indole compounds containing various substituents.

Description

[0001] (1) Technical field [0002] The invention relates to a method for synthesizing imidazo[1,2-a]indole compounds. [0003] (2) Background technology [0004] Nitrogen-containing heterocyclic compounds are ubiquitous in natural products, medicinal chemistry, and materials chemistry. The development of synthetic methods for the preparation of various nitrogen-containing heterocyclic compounds has always been a hot research direction in organic synthetic chemistry. Although a variety of methods have been developed to prepare nitrogen-containing heterocyclic compounds, the reactions are relatively complex, so a general method that uses easily prepared synthons as raw materials and can selectively control substituents still needs to be developed. Imidazole and its derivatives are an important class of nitrogen-containing heterocyclic compounds. The research on the construction of imidazole skeleton compounds has made great progress. However, the research on novel and efficient...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D487/04
CPCC07D487/04
Inventor 金红卫陆露露刘道宏
Owner ZHEJIANG UNIV OF TECH
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