Preparation method of trifluoromethylated 2,4-quinolinedione compound

A technology of trifluoromethylation and quinoline dione, applied in the direction of organic chemistry, etc., can solve problems such as limited amplification application, and achieve the effect of reducing side reactions and mild reaction conditions

Active Publication Date: 2022-02-08
GUANGXI TEACHERS EDUCATION UNIV
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  • Abstract
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  • Claims
  • Application Information

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Problems solved by technology

However, this reaction requires the use of an equivalent amount of copper perchlorate as an oxidant, which limits the scale-up application of this reaction to some extent.

Method used

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  • Preparation method of trifluoromethylated 2,4-quinolinedione compound
  • Preparation method of trifluoromethylated 2,4-quinolinedione compound
  • Preparation method of trifluoromethylated 2,4-quinolinedione compound

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Embodiment Construction

[0017] The present invention will be further described in detail below in conjunction with the embodiments, so that those skilled in the art can implement it with reference to the description.

[0018] It should be noted that the experimental methods described in the following embodiments, unless otherwise specified, are conventional methods, and the reagents and materials, unless otherwise specified, can be obtained from commercial sources;

[0019] According to the method reported in the existing literature (Organic & Biomolecular Chemistry, 2015, 13, 5376-5380), the reaction raw materials required for the technology of the present invention were synthesized. Concrete synthetic scheme is as follows:

[0020]

[0021] The preparation method of trifluoromethylated 2,4-quinolinediones, comprising:

[0022] Add N-o-cyanoaryl acrylamide compound, sodium trifluoromethyl sulfinate, photocatalyst and solvent successively into the reactor, then stir the reaction under air atmosph...

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Abstract

The invention discloses a preparation method of a trifluoromethylated 2,4-quinolinedione compound and a preparation method of the trifluoromethylated 2,4-quinolinedione compound. The preparation method comprises the following steps: adding an N-o-cyano aryl acrylamide compound, sodium trifluoromethanesulfinate, a photocatalyst and a solvent into a reactor; stirring and reacting the mixture under the conditions of air atmosphere and visible light irradiation; after the reaction is completed, concentrating the product, and separating by silica gel column chromatography to obtain the trifluoromethylated 2,4-quinolinedione compound after the reaction is completed. According to the method, transition metal catalysis is not needed, the reaction can be carried out at room temperature, oxygen in air is used as an oxidizing agent, and other oxidizing agents with strong oxidizing property can be prevented from being additionally added.

Description

technical field [0001] The invention relates to the technical field of compound synthesis. More specifically, the present invention relates to a method for preparing trifluoromethylated 2,4-quinolinedione compounds. Background technique [0002] As an important class of nitrogen-containing heterocyclic compounds, 2,4-quinolinediones have rich pharmacological activities, such as anticancer, antiviral, and antimalarial. They are also important intermediates for the construction of other nitrogen-containing heterocyclic skeletons. In view of the importance of 2,4-quinolinedione compounds, the development of preparation methods for such compounds has always been an important research topic in the field of organic synthetic chemistry. Due to the extremely strong electronegativity of fluorine atoms, the introduction of trifluoromethyl groups into organic compounds can significantly improve the physical and chemical properties of compounds such as lipophilicity and solubility. B...

Claims

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Application Information

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IPC IPC(8): C07D215/22
CPCC07D215/22Y02P20/584
Inventor 黄俊崔海涛顾运琼徐家丽朱凤婷班彩锦
Owner GUANGXI TEACHERS EDUCATION UNIV
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