Method for catalytically synthesizing 4,6-diaryl pyrimidine-2(1H)-one derivative by using sulfonic acid functional chitosan

A technology for catalyzing chitosan and diarylpyrimidine is applied in the field of catalyzing the synthesis of 4,6-diarylpyrimidin-2-one compounds by sulfonic acid functionalized chitosan, and can solve the problems of low conversion rate and reaction temperature. high, long reaction time and other problems, to achieve the effect of easy separation and recycling, good biocompatibility, simple and convenient post-processing

Inactive Publication Date: 2017-10-20
NANYANG INST OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, these methods still have some disadvantages, such as longer reaction time, higher reaction temperature, lower conversion rate, and the need for special equipment and devices.

Method used

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  • Method for catalytically synthesizing 4,6-diaryl pyrimidine-2(1H)-one derivative by using sulfonic acid functional chitosan
  • Method for catalytically synthesizing 4,6-diaryl pyrimidine-2(1H)-one derivative by using sulfonic acid functional chitosan
  • Method for catalytically synthesizing 4,6-diaryl pyrimidine-2(1H)-one derivative by using sulfonic acid functional chitosan

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0038] 0.11g (1.0mmol) benzaldehyde, 0.12g (1.0mmol) acetophenone, 0.07g (1.2mmol) urea and 15.4mg sulfonic acid functionalized chitosan catalyst were added in a single-necked flask, and were heated at 90 The reaction was heated at ℃, and the reaction was tracked and monitored by thin-layer chromatography; the reaction was completed after 30 minutes. After the reaction system was cooled to room temperature, ethyl acetate was added thereto, filtered, and the filtrate was distilled under reduced pressure. The obtained crude product was recrystallized with ethanol to obtain 4 , The pure product of 6-diphenylpyrimidin-2(1H)-one has a yield of 93%; the measured melting point is 216-218°C, which is consistent with the literature reports.

[0039] The filtered solid was washed three times with ethanol and dried in vacuum before being reused.

Embodiment 2

[0041] Add 0.12 g (1.0 mmol) 4-methylbenzaldehyde, 0.12 g (1.0 mmol) acetophenone, 0.07 g (1.2 mmol) urea, and 19.2 mg sulfonic acid functionalized chitosan catalyst into a one-necked flask without solvent Heating the reaction at 90°C under the conditions, using thin-layer chromatography to track and monitor the reaction, the reaction was completed after 35 minutes, after the reaction system was cooled to room temperature, ethyl acetate was added to it, filtered, the filtrate was distilled under reduced pressure, and the obtained crude product was recrystallized with ethanol The pure product of 4-(4-methylphenyl)-6-phenylpyrimidin-2(1H)-one can be obtained with a yield of 92%; the measured melting point is 288-289°C, which is consistent with the literature reports.

[0042] The filtered solid was washed three times with ethanol and dried in vacuum before being reused.

Embodiment 3

[0044] Add 0.11 g (1.0 mmol) benzaldehyde, 0.13 g (1.0 mmol) 4-methylacetophenone, 0.07 g (1.2 mmol) urea, and 19.8 mg sulfonic acid functionalized chitosan catalyst into a one-necked flask without solvent Heat the reaction at 90°C under the conditions, and use thin-layer chromatography to track and monitor the reaction; after 30 minutes, the reaction is completed. After the reaction system is cooled to room temperature, ethyl acetate is added to it, filtered, and the filtrate is distilled under reduced pressure. The obtained crude product is recrystallized with ethanol. The pure product of 4-phenyl-6-(4-methylphenyl)pyrimidin-2(1H)-one can be obtained with a yield of 90%; the measured melting point is 285-286° C., which is consistent with literature reports.

[0045] The filtered solid was washed three times with ethanol and dried in vacuum before being reused.

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Abstract

The invention belongs to the technical field of green organic chemistry, and particularly relates to a method for catalytically synthesizing a pyrimidones derivative by using natural polymer modified sulfonic acid functional chitosan. The method comprises the following steps: adding aromatic aldehyde, aromatic ketone, urea and a sulfonic acid functional chitosan catalyst in a flask; carrying out heating reaction at the temperature of 90 DEG C under the condition that a solvent does not exist to obtain a coarse product; and carrying out recrystallization on the coarse product to obtain a pure 4,6-diaryl pyrimidine-2(1H)-one derivative. The catalyst has the advantages of good catalyst biocompatibility, high catalytic activity, easiness in separation and recycling, environmental friendliness and the like, and has wide development prospect in the field of organic synthesis and catalysis.

Description

technical field [0001] The invention belongs to the technical field of green organic chemistry, and in particular relates to a method for catalytically synthesizing 4,6-diarylpyrimidin-2(1H)-one compounds with sulfonic acid functionalized chitosan modified by natural polymers. Background technique [0002] Pyrimidinone derivatives are an important class of nitrogen-containing heterocyclic compounds, which have important physiological and pharmacological activities, and are widely used in the fields of anti-virus, anti-tumor, anti-bacterial and anti-inflammatory, and can also be used as the lead for the development of anti-cancer drugs . Therefore, the synthesis of pyrimidinone series compounds has important research significance. As a typical representative of pyrimidinones, 4,6-diarylpyrimidin-2(1H)-ones are traditionally prepared by aromatic aldehydes, aromatic ketones, and urea under the action of acidic catalysts. In recent years, some new catalysts have been applied t...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D239/36
CPCC07D239/36
Inventor 王英磊李入林杜朝军刘学国李文欢
Owner NANYANG INST OF TECH
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