Photocatalytic oxidation synthesis method of benzocoumarin compound

A technology of benzocoumarin and photocatalytic oxidation, which is applied in the direction of organic chemistry, can solve the problems of excessive oxidant not being environmentally friendly and metal residues, and achieve the effects of reducing environmental costs, saving energy, and overcoming metal residues

Active Publication Date: 2020-03-06
ZHEJIANG UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, this type of reaction system generally uses transition metal catalysts and excessive oxidants. On the one hand, it may cause metal residues in the product, and on the other hand, the use of excessive oxidants is not environmentally friendly.

Method used

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  • Photocatalytic oxidation synthesis method of benzocoumarin compound
  • Photocatalytic oxidation synthesis method of benzocoumarin compound
  • Photocatalytic oxidation synthesis method of benzocoumarin compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0027] Embodiment 1: the preparation of benzocoumarin (formula (2-1))

[0028] In a sealed 35mL tube equipped with a magnetic stirrer, add 0.5mmol of 2-phenylbenzoic acid (formula (1-1)), 0.025mmol of DDQ and 4mL of 1,2-dichloroethane, and replace with oxygen Air in the tube, then add 0.025mmol of TBN, seal the bottle mouth. After reacting for 12 hours at room temperature under the irradiation of a 18W blue LED lamp, the solvent was evaporated under reduced pressure, and then separated by column chromatography, using a mixture of petroleum ether / ethyl acetate with a volume ratio of 50:1 as the eluent to collect the target compound The eluent was evaporated to remove the solvent to obtain the product benzocoumarin, and the separation yield was 99%.

Embodiment 2

[0029] Embodiment 2: the preparation of benzocoumarin (formula (2-1))

[0030] The reaction steps are the same as in Example 1, except that the amount of DDQ is changed to 0.01 mmol, and the isolated yield of benzocoumarin is 67%.

Embodiment 3

[0031] Embodiment 3: the preparation of benzocoumarin (formula (2-1))

[0032] The reaction steps are the same as in Example 1, except that the amount of TBN is changed to 0.01 mmol, and the isolated yield of benzocoumarin is 61%.

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Abstract

The invention discloses a photocatalytic oxidation synthesis method of a benzocoumarin compound. A 2-aryl-aryl formic acid compound is used as a reaction raw material; 2,3-dichloro-5,6-dinitrile-1,4-benzoquinone (DDQ) and tert-butyl nitrite (TBN) are used as catalysts, oxygen is used as an oxidant, a reaction substrate is subjected to a reaction in an organic solvent under the conditions of normaltemperature, normal pressure and blue light irradiation, and after the reaction is finished, separation treatment is performed to obtain the benzocoumarin compound. Compared with a traditional heating reaction, the synthesis method provided by the invention has the advantages that the illumination reaction can save energy; oxygen is used as a terminal oxidant, so that the environmental cost is reduced; a transition metal catalyst is not used, so that the problem of metal residues in the product can be solved.

Description

technical field [0001] The invention relates to a photocatalytic oxidation synthesis method of benzocoumarin compounds. Background technique [0002] Coumarin compounds are a class of lactone compounds that widely exist in nature, and coumarin structural units are also common in natural products, medicine, pesticides and optoelectronic materials. Studies have proved that coumarin compounds have good pharmaceutical activity and can be used in anticancer, antitumor, antibacterial, anticoagulant, etc.; coumarin compounds have excellent photoelectric properties, and can be used in organic fluorescent dyes, organic Light-emitting diodes, fluorescent probes, etc. have a wide range of applications. Among various types of coumarin derivatives, benzocoumarin compounds are one of the most important ones. [0003] Due to the important role of benzocoumarin compounds, the synthesis of these compounds has received continuous attention, and their synthesis methods have also been continu...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D311/80C07D311/78C07D493/04C07D495/04
CPCC07D311/78C07D311/80C07D493/04C07D495/04
Inventor 沈振陆李静汪一青李美超胡宝祥
Owner ZHEJIANG UNIV OF TECH
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