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Method for synthesizing 2-aryl benzopyrone flavonoid derivatives

A synthesis method and technology of pyrone, which are applied in the fields of drug combination, organic chemistry, metabolic diseases, etc., can solve the problems of high operation difficulty, cumbersome post-processing, long reaction period, etc., and achieve simple post-processing, shortened reaction time, heating fast effect

Active Publication Date: 2019-04-19
HEILONGJIANG UNIV
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  • Claims
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Problems solved by technology

[0009] The purpose of the present invention is to provide a 2-arylbenzopyrone in order to solve the technical problems of low yield, long reaction cycle, cumbersome post-treatment and high operation difficulty in the existing synthesis method of ketone flavonoid derivatives Synthetic method of flavonoid derivatives

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  • Method for synthesizing 2-aryl benzopyrone flavonoid derivatives
  • Method for synthesizing 2-aryl benzopyrone flavonoid derivatives
  • Method for synthesizing 2-aryl benzopyrone flavonoid derivatives

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specific Embodiment approach 1

[0035] Embodiment 1: The synthesis method of 2-arylbenzopyrone flavonoid derivatives in this embodiment is carried out according to the following steps:

[0036] 1. In a microwave test tube, add 1.0mmol of aryl ethyl ketone, 10ml of organic solvent and 10ml of saturated alkaline aqueous solution in sequence, then dropwise add 1.2mmol of arylformyl chloride, and carry out microwave irradiation under the conditions of 60°C and microwave 100-150W. Irradiate for 5-6 minutes, then add 2.0 mg of phase transfer catalyst and 5 ml of saturated alkali solution, and then irradiate with microwave for 3-4 minutes under the condition of microwave 100-150W. Recrystallization to obtain yellow powder β-propanedione compound;

[0037] 2. Add the β-propanedione compound into the microwave test tube, then add 8ml of organic solvent, 1.02mmol of trifluoromethanesulfonic acid and CuCl 2110 mg was dissolved, and irradiated by microwave at 65°C and microwave 100-150W for 5-6min, poured the reaction ...

specific Embodiment approach 2

[0038] Specific embodiment 2: The difference between this embodiment and specific embodiment 1 is that the aryl ethyl ketone described in step 1 is o-hydroxyacetophenone, 2,4-dihydroxyacetophenone or 2-hydroxy-4-methoxy Acetophenone. Others are the same as in the first embodiment.

specific Embodiment approach 3

[0039] Embodiment 3: The difference between this embodiment and Embodiment 1 or 2 is that the aryl formyl chloride described in step 1 is benzoyl chloride, p-methoxybenzoyl chloride or p-chlorobenzoyl chloride. Others are the same as in the first or second embodiment.

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Abstract

The invention relates to a method for synthesizing 2-aryl benzopyrone flavonoid derivatives, and relates to a method for synthesizing a compound, the method for synthesizing 2-aryl benzopyrone flavonoid derivatives is suitable for the synthesis of 2-aryl benzopyrone flavonoid derivatives containing different substituents. The method aims to solve the technical problems of low yield, long reactionperiod, and complicated post-treatment and high operation difficulty of the existing synthesis method of the ketone flavonoid derivative. The method comprises the following steps of: 1, preparing beta-propanedione compounds; 2, preparing flavonoid compound 2-aryl benzopyranones. The method completes esterification and rearrangement in one step, which is simple and practical, reduces intermediate links of reaction, saves separation and purification of intermediate products, improves utilization rate of raw materials, reduces reaction temperature, shortens reaction time under microwave radiation, reduces solvent consumption, the post-treatment is relatively simple, the yield is relatively high and no by-products exist, and can also react in the presence of a small amount of water, the reaction is easy to operate, and the method is suitable for industrial production. The method belongs to the technical field of compound synthesis.

Description

technical field [0001] The invention relates to a compound synthesis method, which is suitable for the synthesis of 2-arylbenzopyrone flavonoid derivatives containing different substituents. Background technique [0002] As important natural products, flavonoids are widely used in the fields of fine chemicals such as medicine and spices. These compounds have been proven to have anti-oxidative, anti-proliferative, anti-tumor, anti-microbial and anti-inflammatory activities and other physiological effects, and have been used to treat cancer, cardiovascular diseases, neurodegenerative diseases and so on. Most of the known flavonoid monomers in nature are isolated from plants, but the content extracted from natural plants is generally very low, and the required cost is relatively high. Therefore, it is of great significance to obtain flavonoids by chemical total synthesis. At present, some literatures have reported the chemical synthesis technology of flavonoids. There are two...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D311/30A61P29/00A61P7/02A61P31/00A61P3/04A61P35/00A61P25/00A61P25/28
CPCA61P3/04A61P7/02A61P25/00A61P25/28A61P29/00A61P31/00A61P35/00C07D311/30
Inventor 初文毅杨忠文孙志忠姜洪硕付万勇武洪峰安琪
Owner HEILONGJIANG UNIV
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