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Method for synthesizing 3, 4-dihydropyrimidinone/thione heterocyclic compound through tantalum nitride photocatalysis

A technology for dihydropyrimidinone and heterocyclic compounds, applied in the field of organic synthesis, can solve the problems of harsh reaction conditions, excessive use of organic solvents, low yield and the like

Active Publication Date: 2020-10-23
DALIAN POLYTECHNIC UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

At present, the synthesis methods and mechanisms of 3,4-dihydropyrimidinone / thione heterocyclic compounds have been widely studied, but most of the synthesis methods have some shortcomings, such as: harsh reaction conditions, excessive use of organic solvents, low yield or pollute the environment

Method used

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  • Method for synthesizing 3, 4-dihydropyrimidinone/thione heterocyclic compound through tantalum nitride photocatalysis
  • Method for synthesizing 3, 4-dihydropyrimidinone/thione heterocyclic compound through tantalum nitride photocatalysis
  • Method for synthesizing 3, 4-dihydropyrimidinone/thione heterocyclic compound through tantalum nitride photocatalysis

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0027] (1) Accurately weigh 5.0mmol benzaldehyde, 7.5mmol ethyl acetoacetate and 7.5mmol urea in a 15.0mL pressure-resistant bottle;

[0028] (2) Add 70 mg of tantalum nitride to the pressure-resistant bottle in step (1);

[0029] (3) The pressure-resistant bottle was reacted with 300W xenon light for 2.5 hours at 20.0°C, 30.0°C, 40.0°C, 50.0°C, 60.0°C, 70.0°C, 80.0°C, 90.0°C and 100.0°C in a water bath, and then cooled to room temperature , mixed the product with cold water to precipitate the solid, filtered, and dried at 80.0°C to constant weight to obtain the crude product;

[0030] (4) Recrystallize the product obtained in step (3) with 78.0°C hot ethanol to obtain the target product;

[0031] (5) The target product was subjected to NMR test to further confirm the target product.

[0032] The highest yield was 61.4% at 90.0℃ under different reaction temperature conditions.

[0033] The reaction equation of the present embodiment is as follows:

[0034]

Embodiment 2

[0036] (1) Accurately weigh 5.0mmol benzaldehyde, 7.5mmol ethyl acetoacetate and 7.5mmol urea in a 15.0mL pressure-resistant bottle;

[0037] (2) Add 70 mg of tantalum nitride to the pressure-resistant bottle in step (1);

[0038] (3) Under the condition of 90.0°C water bath, use a 300W xenon lamp to light the reaction for 0.5h, 1.0h, 1.5h, 2.0h, 3.0h respectively, then cool to room temperature, mix the product with cold water to precipitate the solid, filter, 80 °C and dried to constant weight to obtain the crude product;

[0039] (4) Recrystallize the product obtained in step (3) with 78°C hot ethanol to obtain the target product;

[0040] (5) The target product was subjected to NMR test to further confirm the target product.

[0041] Under different reaction time conditions, the yield was the highest at 2.5h, reaching 64.4%.

Embodiment 3

[0043] (1) Accurately weigh 5.0mmol benzaldehyde, 7.5mmol ethyl acetoacetate and 7.5mmol urea in a 15.0mL pressure-resistant bottle;

[0044] (2) Add tantalum nitride to the pressure bottle in step (1), the dosage of tantalum nitride is 5.0mg, 10.0mg, 20.0mg, 50.0mg, 90.0mg respectively;

[0045] (3) React the pressure-resistant bottle with a 300W xenon lamp for 2.5 hours in a water bath at 90.0°C, then cool it to room temperature, mix the product with cold water to precipitate a solid, filter, and dry at 80°C to constant weight to obtain a crude product;

[0046] (4) Recrystallize the product obtained in step (3) with 78°C hot ethanol to obtain the target product;

[0047] (5) The target product was subjected to NMR test to further confirm the target product.

[0048] The yield of 70.0g was the highest under different catalyst dosage conditions, reaching 69.7%.

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Abstract

The invention discloses a method for synthesizing a 3, 4-dihydropyrimidinone / thione heterocyclic compound through tantalum nitride photocatalysis, and belongs to the technical field of organic synthesis. The method comprises the following steps: taking tantalum nitride as a photocatalyst, taking aromatic aldehyde, ethyl acetoacetate or methyl acetoacetate and urea or thiourea as substrates, and carrying out photocatalytic synthesis under an illumination condition to obtain the 3, 4-dihydropyrimidinone / thione heterocyclic compound. According to the method, tantalum nitride is used as a catalyst, photocatalysis is used for reaction, and the method has the advantages of simple process, easily controlled reaction conditions, environmental friendliness, easily available raw materials, mild reaction conditions, high yield and the like. Meanwhile, the substrate is wide in universality, various 3, 4-dihydropyrimidinone / thioketone heterocyclic compounds can be synthesized by utilizing differentsubstrates, and the method has a wide application prospect.

Description

technical field [0001] The invention relates to a new method for synthesizing 3,4-dihydropyrimidinone / thione heterocyclic compounds from aromatic aldehyde, ethyl acetoacetate or methyl acetoacetate and urea or thiourea by tantalum nitride photocatalysis, belonging to organic synthesis technology field. Background technique [0002] In 1893, Italian chemist Pietro Biginelli first reported the synthesis of 3,4-dihydropyrimidinone / thione heterocyclic compounds by using aromatic aldehydes, ethyl acetoacetate and urea under the catalysis of sulfuric acid in a "one-pot method". Therefore, this synthetic method is called Biginelli reaction. Studies have found that 3,4-dihydropyrimidinone / thione heterocyclic compounds have calcium antagonistic activity and play an important role in anti-stress and inhibition of fatty acid conversion. At present, the synthesis methods and mechanisms of 3,4-dihydropyrimidinone / thione heterocyclic compounds have been widely studied, but most of the s...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D239/22
CPCC07D239/22
Inventor 马纪亮孙润仓李彦聪金栋女李澳华
Owner DALIAN POLYTECHNIC UNIVERSITY