Preparation method of 1, 4-dihydropyridine compound

A technology for dihydropyridine and compound, which is applied in the field of preparation of 1,4-dihydropyridine compounds, can solve problems such as environmental pollution, and achieve the effects of no environmental pollution, easy recycling and simple reaction operation.

Inactive Publication Date: 2014-09-10
SHANGHAI APPLIED TECHNOLOGIES COLLEGE
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0003] At present, the more commonly used synthetic method of 1,4-dihydropyridine compounds is obtained through the Hantzsch reaction, but this synthetic method uses highly corrosive inorganic acids and volatile organic solvents in the synthetic process or is harmful to the environment. Technical issues such as contaminated catalysts

Method used

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  • Preparation method of 1, 4-dihydropyridine compound
  • Preparation method of 1, 4-dihydropyridine compound
  • Preparation method of 1, 4-dihydropyridine compound

Examples

Experimental program
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Effect test

Embodiment 1

[0028] A preparation method of 1,4-dihydropyridine compounds, wherein the structural formula of the 1,4-dihydropyridine compounds is as follows:

[0029]

[0030] Wherein substituent R is 3-OCH 3 -4-OH group;

[0031] A kind of above-mentioned preparation method of 1,4-dihydropyridine compounds, the reaction equation of its synthetic process is as follows:

[0032] That is to say, aromatic aldehyde, ethyl acetoacetate and ammonium acetate are reacted at a temperature of 80°C for 3-4 hours in the presence of the catalyst, the ionic liquid SiPIPPWO. After the reaction, cool to room temperature, add ethyl acetate, and filter to remove the catalyst, the ionic liquid SiPIPPWO. , the filtrate was rotary evaporated to remove the solvent to obtain a crude product, and then recrystallized with 95% ethanol to obtain 1,4-dihydropyridine compounds;

[0033] The aromatic aldehyde is 3-methoxy-4-hydroxybenzaldehyde;

[0034] The aromatic aldehyde, ethyl acetoacetate, and ammonium a...

Embodiment 2

[0048] A kind of preparation method of 1,4-dihydropyridine compound, the structural formula of described 1,4-dihydropyridine compound is as follows:

[0049]

[0050] Wherein the substituent R is 3,4-OCH 2 O base;

[0051] A kind of above-mentioned preparation method of 1,4-dihydropyridine compounds, the reaction equation of its synthetic process is as follows:

[0052] That is to say, aromatic aldehyde, ethyl acetoacetate and ammonium acetate are reacted at a temperature of 80°C for 3-4 hours in the presence of the catalyst, the ionic liquid SiPIPPWO. After the reaction, cool to room temperature, add ethyl acetate, and filter to remove the catalyst, the ionic liquid SiPIPPWO. , the filtrate was rotary evaporated to remove the solvent to obtain a crude product, and then recrystallized with 95% ethanol to obtain 1,4-dihydropyridine compounds;

[0053] Described aromatic aldehyde is 3,4-dioxymethylene benzaldehyde;

[0054] The aromatic aldehyde, ethyl acetoacetate, and a...

Embodiment 3

[0067] A kind of preparation method of 1,4-dihydropyridine compound, the structural formula of described 1,4-dihydropyridine compound is as follows:

[0068]

[0069] Wherein substituent R is -H group;

[0070] A kind of above-mentioned preparation method of 1,4-dihydropyridine compounds, the reaction equation of its synthetic process is as follows:

[0071] That is to say, aromatic aldehyde, ethyl acetoacetate and ammonium acetate are reacted at a temperature of 80°C for 3-4 hours in the presence of the catalyst, the ionic liquid SiPIPPWO. After the reaction, cool to room temperature, add ethyl acetate, and filter to remove the catalyst, the ionic liquid SiPIPPWO. , the filtrate was rotary evaporated to remove the solvent to obtain a crude product, and then recrystallized with 95% ethanol to obtain 1,4-dihydropyridine compounds;

[0072] Described aromatic aldehyde is benzaldehyde;

[0073] The aromatic aldehyde, ethyl acetoacetate, and ammonium acetate used in the ab...

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Abstract

The invention discloses a preparation method of a 1, 4-dihydropyridine compound, the structural formula of which is shown as in the specification, wherein R is -H, 2-OH, 3-NO2, 4-OCH3, 4-CH3, 4-F, 3-OCH3-4-OH or 3, 4-OCH2O. The preparation method comprises the following steps: in the presence of an ionic liquid SiPIPPWO, carrying out a reaction on aromatic aldehyde, ethyl acetoacetate and ammonium acetate for 3-4 hours at 80 DEG C; and after reaction, cooling to room temperature, adding ethyl acetate, filtering to remove the ionic liquid SiPIPPWO, rotatably distilling the filtrate to remove the solvent and recrystallizing by 95% ethanol to obtain the 1, 4-dihydropyridine compound. The preparation method is high in yield which can reach 82-90%, and the ionic liquid is low in cost and easy to obtain, free from environmental pollution, easy to recover and use and simple in post-treatment of products.

Description

technical field [0001] The invention relates to a preparation method of 1,4-dihydropyridine compounds. The method uses ionic liquid SiPIPPWO to catalyze and synthesize 1,4-dihydropyridine compounds. Background technique [0002] 1,4-Dihydropyridine compounds have significant pharmacological activity, such as being widely used in Ca 2+ Channel blockers are used to treat cardiovascular and cerebrovascular diseases, etc., and have good prospects in the fields of biology and medicine. Therefore, the development and synthesis of 1,4-dihydropyridine compounds with different substituents has attracted much attention in organic chemistry. [0003] At present, the more commonly used synthetic method of 1,4-dihydropyridine compounds is obtained through the Hantzsch reaction, but this synthetic method uses highly corrosive inorganic acids and volatile organic solvents in the synthetic process or is harmful to the environment. Contaminated catalysts and other technical issues. Conte...

Claims

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Application Information

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IPC IPC(8): C07D211/90C07D211/02B01J31/18
CPCC07D211/90C07D211/02
Inventor 康丽琴曹智珺完颜新月
Owner SHANGHAI APPLIED TECHNOLOGIES COLLEGE
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