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Synthetic method of diarylpyridines

A technology for diarylpyridines and a synthesis method, which is applied in the field of synthesis of similar compounds, can solve problems such as low yield and long reaction steps, and achieve the effects of improving synthesis efficiency, low preparation cost and shortening reaction time.

Inactive Publication Date: 2011-12-14
孙光辉
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The reaction steps are long and the yield is not high, although it has been reported in the literature that the synthesis of disubstituted pyridines can use the method of 1,5 diketone ring closure
However, this method is only limited to various 1,5 diketones as raw materials, and the method for synthesizing disubstituted pyridines directly from epichlorohydrin and aldehydes has not been reported in the literature.

Method used

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  • Synthetic method of diarylpyridines

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0024] 1) 1 weight part of carbene catalyst 3-benzyl-5-(2-hydroxyethyl)-4-methylthiazole chloride salt, 1 weight part of triethylamine), 100 weight parts of epichlorohydrin Add benzene into the container at room temperature and stir to react;

[0025] 2) Add 200 parts by weight of substituted aldehyde, heat and stir until the temperature of the mixture is 50°C, hold for 20 minutes or irradiate under microwave with a frequency of 150Hz for 5 minutes;

[0026] 3) Add 100 parts by weight of ammonium acetate and stir evenly;

[0027] 4) Heat and stir until the temperature of the mixture is 50°C, hold for 20 minutes or irradiate under microwave frequency of 150Hz for 5 minutes;

[0028] 5) After the reaction, benzene was evaporated to dryness, and the solid was recrystallized from ethanol to obtain diarylpyridine drugs.

[0029] The solvent is benzene, toluene or xylene.

Embodiment 2

[0031] 1) 2 parts by weight of carbene catalyst 3-benzyl-5-(2-hydroxyethyl)-4-methylthiazole chloride, 2 parts by weight of triethylamine), 200 parts by weight of epichlorohydrin Add toluene into the container and stir at room temperature to react;

[0032] 2) Add 400 parts by weight of substituted aldehyde, heat and stir until the temperature of the mixture is 100°C, hold the temperature for 40 minutes or irradiate for 15 minutes under microwave with a frequency of 500Hz;

[0033] 3) Add 200 parts by weight of ammonium acetate and stir evenly;

[0034] 4) Heat and stir until the temperature of the mixture is 100°C, hold for 40 minutes or irradiate for 15 minutes under microwaves with a frequency of 150-500 Hz;

[0035] 5) After the reaction, the toluene was evaporated to dryness, and the solid was recrystallized from ethanol to obtain diarylpyridine drugs.

Embodiment 3

[0037] 1) 2 parts by weight of carbene catalyst 3-benzyl-5-(2-hydroxyethyl)-4-methylthiazole chloride, 2 parts by weight of triethylamine), 200 parts by weight of epichlorohydrin Add xylene and stir in the container at room temperature to react;

[0038] 2) Add 400 parts by weight of substituted aldehyde, heat and stir until the temperature of the mixture is 80°C, hold for 30 minutes or irradiate under microwave with a frequency of 400Hz for 10 minutes;

[0039] 3) Add 200 parts by weight of ammonium acetate and stir evenly;

[0040] 4) Heat and stir until the temperature of the mixture is 80°C, hold for 30 minutes or irradiate for 12 minutes under microwave frequency of 150-400Hz;

[0041] 5) After the reaction, evaporate the xylene to dryness, and recrystallize the solid with ethanol to obtain diarylpyridine drugs.

[0042] Compound Identification:

[0043] 1,5-Diphenylpyridine: Melting point: 79-80°C, compared with literature (Wenkert, E.; Hanna, J.M.; Leftin, M. H.; Mic...

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Abstract

The invention discloses a method for synthesizing diarylpyridine medicines. The method comprises the following steps of: 1) adding 1 to 2 weight parts of carbene catalyst, namely 3-benzyl-5-(2-hydroxyethyl)-4-methylthiazolium chloride, 1 to 2 weight parts of triethylamine, 100 to 200 weight parts of epichlorohydrin and a solvent into a container and stirring to react at normal temperature; 2) adding 200 to 400 weight parts of substituted aldehyde, heating and stirring until the temperature of mixed liquor is 50 to 100 DEG C, and keeping the temperature for 20 to 40 minutes or radiating for 5 to 15 minutes under the microwave with the frequency of between 150 and 500Hz; 3) adding 100 to 200 weight parts of ammonium acetate and stirring uniformly; 4) heating and stirring until the temperature of mixed liquor is 50 to 100 DEG C, and keeping the temperature for 20 to 40 minutes or radiating for 5 to 15 minutes under the microwave with the frequency of between 150 and 500Hz; and 5) evaporating the solvent to dryness after the reaction is finished, and recrystallizing a solid by using ethanol to obtain the diarylpyridine medicines. By the method, the reaction time is shortened, the energy consumption is reduced, and the synthetic efficiency is improved. The catalyst which is nontoxic and harmless to the environment is adopted.

Description

technical field [0001] The invention relates to a synthesis method of a compound, in particular to a synthesis method of a diarylpyridine drug. Background technique [0002] Diarylpyridine compounds are a class of compounds with good biological activity. A large number of natural drug molecules containing pyridine structure have been isolated in nature. This type of molecule has physiological activities such as antifungal and anti-inflammatory, and this type of molecule also shows good anti-cancer and anti-virus effects. biological activity. Therefore, this type of molecule has a good prospect for drug development. [0003] The existing synthetic methods of disubstituted pyridine compounds are carried out by multi-step organic synthesis reactions. The reaction steps are long and the yield is not high, although it has been reported in the literature that the synthesis of disubstituted pyridines can use the method of 1,5 diketone ring closure. However, this method is limit...

Claims

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Application Information

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IPC IPC(8): C07D213/16C07D213/09C07D213/24
Inventor 孙光辉景崤壁
Owner 孙光辉
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