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Method for preparing 1, 4-dihydropyridine derivative containing azulene ring structure

A technology of dihydropyridine and its derivatives, which is applied in the field of medicine and chemical industry, can solve the problems that the catalyst cannot be recycled, the product purification process is complicated, and the catalytic activity is low, so as to reduce the reaction time and the amount of catalyst used, and improve economic benefits and environmental protection. Benefits, high catalytic efficiency

Pending Publication Date: 2021-06-11
马鞍山市泰博化工科技有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] For the preparation of 1,4-dihydropyridine derivatives containing an azulene ring structure in the prior art, the catalysts existing in the method cannot be recycled, the environment is seriously polluted and the catalytic activity is relatively low, the reaction time is long, and the product purification process is complicated. To solve the problems of continuous industrialized large-scale production, the present invention provides a method for preparing 1,4-dihydropyridine derivatives containing an azulene ring structure

Method used

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  • Method for preparing 1, 4-dihydropyridine derivative containing azulene ring structure
  • Method for preparing 1, 4-dihydropyridine derivative containing azulene ring structure
  • Method for preparing 1, 4-dihydropyridine derivative containing azulene ring structure

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Experimental program
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Effect test

Embodiment 1

[0034] Add 1.0mmol 1-formyl azulene-3-carboxylic acid to a 50ml three-neck flask with a spherical condenser, a thermometer and a stirring bar containing 7ml of a mixed solvent (the volume ratio of tert-butanol-ethyl acetate is 9:1) Methyl ester, 1.6mmol methyl acetoacetate, 1.8mmol ammonium acetate, stirred at room temperature, mixed uniformly, then added 0.03mmol acidic ionic liquid, mixed uniformly. Heating in an oil bath, uniformly warming up to reflux (steam does not exceed the second ball of the spherical condenser), keeping the reflux reaction for 142min, TLC (silica gel thin plate chromatography, developing agent is V (benzene): V (ethyl acetate) = 93 : 7) monitoring, the raw material point disappears, and the reaction ends. Turn off the heating and stirring, the reaction liquid is naturally cooled to room temperature, a large amount of solids precipitate out, crush the solids, let stand for 36 hours, filter under reduced pressure, filter the residue through a mixed sol...

Embodiment 2

[0039] Add 1.0mmol 1-formyl azulene-3-carboxylic acid to a 50ml three-neck flask with a spherical condenser, a thermometer and a stirring bar containing 8ml of a mixed solvent (the volume ratio of tert-butanol-ethyl acetate is 9:1.2) Methyl ester, 1.7mmol ethyl acetoacetate, 2.0mmol ammonium acetate, stirred at room temperature, mixed evenly, then added 0.04mmol acidic ionic liquid, mixed evenly. Heat in an oil bath, evenly heat up to reflux (steam does not exceed the second ball of the spherical condenser), keep the reflux reaction for 158min, TLC (silica gel thin plate chromatography, developing solvent is V (benzene): V (ethyl acetate) = 92 : 8) monitoring, the raw material point disappears, and the reaction ends. Turn off the heating and stirring, the reaction liquid is naturally cooled to room temperature, a large amount of solids are precipitated, the solids are crushed, left to stand for 36 hours, vacuum filtered, and the filter residue is passed through a mixed solvent...

Embodiment 3

[0044] Add 1.0mmol 1-formyl azulene-3-carboxylic acid to a 50ml three-neck flask with a spherical condenser, a thermometer and a stirring bar containing 8ml of a mixed solvent (the volume ratio of tert-butanol-ethyl acetate is 9:1.3) Methyl ester, 1.8mmol isopropyl acetoacetate, 2.0mmol ammonium acetate, stirred at room temperature, mixed evenly, then added 0.04mmol acidic ionic liquid, mixed evenly. Heating in an oil bath, uniformly warming up to reflux (steam does not exceed the second ball of the spherical condenser), keeping the reflux reaction for 181min, TLC (silica gel thin plate chromatography, developing solvent is V (benzene): V (ethyl acetate) = 92 : 8) monitoring, the raw material point disappears, and the reaction ends. Turn off the heating and stirring, the reaction liquid is naturally cooled to room temperature, and a large amount of solids are precipitated, crushed solids, left to stand for 36 hours, and filtered under reduced pressure, and the filter residue i...

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Abstract

The invention discloses a method for preparing a 1, 4-dihydropyridine derivative containing an azulene ring structure, and belongs to the technical field of pharmaceutical chemicals. The method comprises the following steps: adding 1-formyl azulen-3-methyl formate, acetoacetate, 3-amino-2-butenoic acid ester or ammonium acetate into a mixed solvent, and uniformly stirring at room temperature; then, adding acidic ionic liquid, and uniformly mixing; and finally, carrying out reflux reaction under a heating condition to generate the 1, 4-dihydropyridine derivative containing the azulene ring structure. The structural formula of the acidic ionic liquid is as follows, the acidic ionic liquid is used as the catalyst, and the selectivity and the catalytic activity of the acidic ionic liquid are relatively high, so that the yield of the obtained product can be effectively improved, generated byproducts are reduced, recycling of the catalyst is realized, and the economic benefit and the environmental benefit are greatly improved.

Description

technical field [0001] The invention belongs to the technical field of medicine and chemical engineering, and more specifically relates to a method for preparing 1,4-dihydropyridine derivatives containing an azulene ring structure. Background technique [0002] Pyridine and its derivatives are an important class of heterocyclic compounds, which exist in many natural products and have a wide range of applications, such as medicine, pesticides, rubber, dyes and other fields. As one of the pyridine derivatives, 1,4-dihydropyridine derivatives have various physiological activities such as antibacterial, anticancer, antitumor, antioxidative, antidiabetic and calcium antagonists, and can be used for the prevention of cardiovascular diseases At the same time, it has certain curative effect on fatty liver and toxic hepatitis. [0003] Azulene compounds have significant aromaticity, are prone to substitution reactions, and have a wide range of biological activities, and have also be...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D213/80C07D213/803B01J31/02
CPCC07D213/80C07D213/803B01J31/0284B01J31/0285Y02P20/584
Inventor 沈建忠卢华
Owner 马鞍山市泰博化工科技有限公司
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