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Method for catalytically preparing 1,4-dihydropyrido[3,2-c][5,6-c]dicoumarin derivative

A dihydropyridine and catalytic preparation technology, applied in the direction of organic chemistry and the like, can solve the problems of high catalyst consumption, low catalytic activity, long reaction time, etc., and achieve the effects of high economy, simple preparation process operation, and improved utilization rate

Active Publication Date: 2019-07-16
马鞍山市泰博化工科技有限公司
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0006] The purpose of the present invention is to overcome the relatively low catalytic activity of the catalyst existing in the existing 1,4-dihydropyrido[3,2-c][5,6-c] dicoumarin derivative preparation process, and the catalyst consumption More, and the shortcoming of long reaction time provides a method for catalytically preparing 1,4-dihydropyrido[3,2-c][5,6-c]dicoumarin derivatives

Method used

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  • Method for catalytically preparing 1,4-dihydropyrido[3,2-c][5,6-c]dicoumarin derivative
  • Method for catalytically preparing 1,4-dihydropyrido[3,2-c][5,6-c]dicoumarin derivative

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preparation example Construction

[0031] Preparation technique of the present invention, its chemical reaction formula is:

[0032]

[0033] Wherein the molar ratio of 4-aminocoumarin and aromatic aldehyde in the reaction is 2:1, and the molar weight of melamine trisulfonic acid catalyst is 2~6% of the aromatic aldehyde used, preferably 3~5%, and the reaction pressure is an atmospheric pressure , the reflux reaction time is 48~115min, the mass concentration of the reaction solvent acetic acid aqueous solution is 88~94%, is preferably 91~93%, and its volume in milliliters is 5~5~100% of the amount of substance in millimoles of aromatic aldehydes. 8 times, after the reaction is completed, cool to room temperature, let stand, filter with suction, and the filter residue can be directly obtained after vacuum drying 1,4-dihydropyrido[3,2-c][5,6-c] dicoumarol The filtrate mainly composed of melamine trisulfonic acid and acetic acid aqueous solution can also be reused without any treatment.

[0034] Above-mentione...

Embodiment 1

[0038] 2mmol 4-aminocoumarin, 1mmol p-tolualdehyde and 0.04mmol melamine trisulfonic acid catalyst were respectively added to a 50ml three-necked flask equipped with 6ml 93% acetic acid aqueous solution, a condenser tube and a thermometer, and the reaction system was stirred under magnetic stirring. Mix well, heat to reflux to start the reaction, follow the reaction by TLC, and the reaction ends in 57 minutes. After cooling to room temperature, a large amount of solids precipitated, crushed the solids, stood still, and filtered with suction. After the obtained filter residue was vacuum-dried, 0.38 g of white crystalline solids were obtained. The purity measured by high performance liquid chromatography was 99%, and the calculated yield was 92%. The structure was identified. It is 1,4-dihydro-4-(4-methylphenyl)pyrido[3,2-c][5,6-c]dicoumarin. The filtrate was directly added with p-tolualdehyde and 4-aminocoumarin and reused.

[0039] The 1,4-dihydro-4-(4-methylphenyl)pyrido[3,2...

Embodiment 2

[0041] 2mmol 4-aminocoumarin, 1mmol p-fluorobenzaldehyde and 0.06mmol melamine trisulfonic acid catalyst were respectively added to a 50ml three-necked flask equipped with 6ml 91% acetic acid aqueous solution, a condenser tube and a thermometer, and the reaction system was fully Mix, heat to reflux to start the reaction, follow the reaction by TLC, and the reaction ends in 115min. After cooling to room temperature, a large amount of solids precipitated, crushed the solids, stood still, and filtered with suction. After the obtained filter residue was vacuum-dried, 0.34 g of white crystalline solids were obtained. The purity measured by high performance liquid chromatography was 98%, and the calculated yield was 81%. The structure was identified. It is 1,4-dihydro-4-(4-fluorophenyl)pyrido[3,2-c][5,6-c]dicoumarin. Add p-fluorobenzaldehyde and 4-aminocoumarin directly to the filtrate and reuse it.

[0042] The parameters of 1,4-dihydro-4-(4-fluorophenyl)pyrido[3,2-c][5,6-c]dicoum...

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Abstract

The invention discloses a method for catalytically preparing a 1,4-dihydropyrido[3,2-c][5,6-c]dicoumarin derivative and belongs to the technical field of organic synthesis. According to the method forcatalytically preparing the 1,4-dihydropyrido[3,2-c][5,6-c]dicoumarin derivative, disclosed by the invention, the 1,4-dihydropyrido[3,2-c][5,6-c]dicoumarin derivative is prepared and synthesized through subjecting aromatic aldehyde and 4-amino coumarin, which serve as reactants, to a heated refluxing reaction in the presence of a catalyzing system prepared from melamine trisulfonic acid and an acetic acid aqueous solution. According to the method, a novel catalyzing system is employed and has relatively high activity to catalytic preparation of the 1,4-dihydropyrido[3,2-c][5,6-c]dicoumarin derivative, the consumption of a catalyst is low, the cycle performance is good, and the reaction time can be effectively shortened.

Description

technical field [0001] The invention relates to a new method for preparing 1,4-dihydropyrido[3,2-c][5,6-c]dicoumarin derivatives, belonging to the technical field of organic synthesis. Background technique [0002] Coumarin derivatives are an important class of organic heterocyclic compounds. Due to their unique molecular structure, they have obvious biological activities such as anti-coagulation, anti-cancer, anti-virus, anti-bacterial, anti-oxidation and anti-HIV. At the same time, it is also an important class of organic fluorescent chromophores. Through the modification of substituents at different positions on the coumarin ring, different ranges of absorption and fluorescence emission wavelengths can be obtained, thereby displaying different colors and derivatives with strong fluorescence. things. The dicoumarin derivatives containing two coumarin monomers also have a variety of biological activities, and some have been used in clinical treatment, such as pyridocoumari...

Claims

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Application Information

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IPC IPC(8): C07D491/153
CPCC07D491/153
Inventor 卢华沈建忠
Owner 马鞍山市泰博化工科技有限公司
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