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Method for catalytically synthesizing quinoxaline compound

A compound and quinoxaline technology, applied in the field of organic chemical synthesis, can solve the problems of harsh reaction conditions, large loss of catalyst usage, environmental pollution, etc., and achieve the effects of simple preparation, low preparation cost and high catalytic activity

Inactive Publication Date: 2013-06-12
ANHUI UNIVERSITY OF TECHNOLOGY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] The purpose of the present invention is to overcome the disadvantages of serious environmental pollution, harsh reaction conditions, catalyst usage and recycling loss in the prior art, and provide a method for catalytically synthesizing quinoxaline compounds

Method used

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  • Method for catalytically synthesizing quinoxaline compound
  • Method for catalytically synthesizing quinoxaline compound
  • Method for catalytically synthesizing quinoxaline compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0019] Example 1: Combine 10mmol o-phenylenediamine, 10mmol benzil, 0.5mmol IL-SO 3 H-a and 15 mL of water were added to a 50 mL single-neck flask with a stir bar and reflux condenser. The reaction was vigorously stirred at 40°C for 20 min, filtered, and the filter residue was recrystallized with ethanol to obtain pure 2,3-diphenylquinoxaline with a yield of 95%. The polysulfonate ionic liquid and unreacted raw materials in the filtrate can be The treatment cycle is 5 times.

Embodiment 2

[0020] Example 2: Combine 10mmol o-phenylenediamine, 10mmol bis(4-oxymethylbenzene) acyl, 0.6mmol IL-SO 3 H-b and 25mL of water were added to a 100mL single-neck flask with a stir bar and reflux condenser. The reaction was vigorously stirred at 60°C for 50 minutes, filtered, and the filter residue was recrystallized with ethanol to obtain pure 2,3-bis(4-oxymethylphenyl)quinoxaline with a yield of 90%. The filtrate contains polysulfonate ionic liquid And unreacted raw materials can be recycled 5 times without treatment.

Embodiment 3

[0021] Example 3: Combine 10mmol o-phenylenediamine, 10mmol diacetyl, 0.8mmol IL-SO 3 H-b and 15 mL of water were added to a 50 mL single-necked flask with a stir bar and reflux condenser. The reaction was vigorously stirred at 60°C for 60 minutes, filtered, and the filter residue was recrystallized with ethanol to obtain pure 2,3-dimethylquinoxaline with a yield of 87%. The polysulfonate ionic liquid and unreacted raw materials in the filtrate can be left unreacted. The treatment cycle is used 5 times.

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Abstract

The invention provides a method for catalytically synthesizing a quinoxaline compound and belongs to the technical field of organic chemical synthesis. According to the method, in the condensation reaction of quinoxaline compound synthesis, the molar ratio of raw materials, namely o-phenylenediamine to a 1, 2-dicarbonyl compound is 1:1, the molar amount of a multi-sulfonic acid radical ionic liquid catalyst accounts for 5-10% of the molar amount of used o-phenylenediamine or the 1, 2-dicarbonyl compound, the reaction temperature is 40-60 DEG C, the reaction time is 20-120 minutes, the usage amount of water serving as a reaction solvent accounts for 50-90% of the total mass of the materials, and the reaction pressure is 1 atmosphere; and filtration is carried out after reaction is ended, and residues are washed by water and then are recrystallized by alcohol to obtain the pure quinoxaline compound, wherein the multi-sulfonic acid radical ionic liquid and unreacted raw materials in filtrate can be recycled for 5 times without needing treatment. Compared with other synthetic methods in which ionic liquid is taken as the catalyst, the method has the characteristics of high catalytic activity, little usage amount of the catalyst, recycling of the catalyst, little loss of the catalyst, high catalytic yield and the like.

Description

Technical field: [0001] The invention belongs to the technical field of organic chemical synthesis, and specifically relates to a method for catalytically synthesizing quinoxaline compounds. Background technique: [0002] Quinoxaline compounds are an important class of nitrogen-containing benzoheterocyclic compounds, which have many biological activities and a wide range of applications. Many quinoxaline compounds have biological activities such as antibacterial and anti-cancer. Some functionalized quinoxaline compounds are expected to be used as organic semiconductors, chemical switches and supramolecular receptors. Therefore, the preparation of quinoxaline compounds has received increasing attention. Under normal circumstances, quinoxaline compounds can be prepared by catalyzing o-phenylenediamine and 1,2-dicarbonyl compounds in organic solvents such as acetonitrile, ethanol, acetic acid, and the corresponding catalyst is CuSO 4 ·5H 2 O, Ga (OTf) 3 And I 2 . However, the use ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D241/42
CPCY02P20/584
Inventor 岳彩波
Owner ANHUI UNIVERSITY OF TECHNOLOGY