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Method for synthesizing 3-aryl flavone or coumarin compound through photo-initiation, and applications of 3-aryl flavone or coumarin compound

A technology of aryl coumarin and aryl flavonoids, which is applied in the direction of chemical instruments and methods, sugar derivatives, sugar derivatives, etc., can solve the problems of high difficulty and low synthesis efficiency, achieve few by-products, simple method, The effect of high reaction yield

Pending Publication Date: 2020-04-21
YUNNAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] Due to electronic effects and steric hindrance effects, it is very difficult to modify the C-3 site-specific structure of two types of natural products. It is impossible to directly use the isolated flavonoids and coumarin compounds for structural modification, but only through chemical synthesis. method, the functional group to be modified is pre-introduced at this position at the initial stage, and a separate chemical synthesis route needs to be designed for each molecule, so the synthesis efficiency is very low

Method used

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  • Method for synthesizing 3-aryl flavone or coumarin compound through photo-initiation, and applications of 3-aryl flavone or coumarin compound
  • Method for synthesizing 3-aryl flavone or coumarin compound through photo-initiation, and applications of 3-aryl flavone or coumarin compound
  • Method for synthesizing 3-aryl flavone or coumarin compound through photo-initiation, and applications of 3-aryl flavone or coumarin compound

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Experimental program
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Effect test

Embodiment 1

[0040] Synthesis.

[0041] Under a nitrogen atmosphere, 3',4'-dihydroxyflavone (0.1 mmol), iodobenzene (0.1 mmol), cesium carbonate (0.2 mmol) were dissolved in dimethyl sulfoxide (1 mL), After the addition, the reactant was placed at 25°C, irradiated with 450nm light for 26 hours, quenched with dilute hydrochloric acid (1N), the aqueous phase was extracted three times with ethyl acetate (15 ml × 3), and the organic phases were combined , washed with water and saturated brine successively, dried over anhydrous sodium sulfate, concentrated and then column chromatographed to obtain 3-arylflavone derivatives (26.4 mg, 80% yield).

Embodiment 2

[0043] Synthesis.

[0044] Under a nitrogen atmosphere, dissolve 5,4'-dihydroxyflavone (0.1 mmol), p-bromoacetophenone (0.3 mmol), and potassium carbonate (0.5 mmol) in N,N-dimethylformamide (1 ml), after the addition, the reactant was placed under the condition of 50° C., irradiated at 390 nm for 16 hours, quenched the reaction with dilute hydrochloric acid (1N), and the aqueous phase was extracted three times with ethyl acetate (15 ml×3 ), the organic phases were combined, washed with water and saturated brine successively, dried over anhydrous sodium sulfate, concentrated and then column chromatographed to obtain 3-arylflavone derivatives (31.6 mg, 85% yield).

Embodiment 3

[0046] Synthesis.

[0047] Under nitrogen atmosphere, 4'-hydroxy-6-methylflavone (0.1 mmol), m-chlorobenzonitrile (0.5 mmol), potassium bicarbonate (0.4 mmol) were dissolved in N,N-dimethyl In acetamide (1 ml), after the addition was complete, the reactant was placed at 0°C, irradiated at 410 nm for 16 hours, quenched with dilute hydrochloric acid (1N), and the aqueous phase was extracted three times with ethyl acetate (15 ml ×3), the organic phases were combined, washed successively with water and saturated brine, dried over anhydrous sodium sulfate, concentrated and then column chromatographed to obtain 3-arylflavone derivatives (27.5 mg, 78% yield).

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Abstract

The invention relates to a method for synthesizing a 3-aryl flavone or coumarin compound through photo-initiation, and applications of the 3-aryl flavone or coumarin compound. The synthesis method comprises the following steps: exciting a flavone substance by visible light under an alkaline condition, and carrying out a monon transfer reaction with an aryl halide to initiate free radicals so as togenerate a 3-aryl flavone derivative in one step. According to the invention, the photoreaction activity of flavone and coumarin compounds under alkaline conditions is utilized, and the 3-aryl flavone or coumarin compound is synthesized through a one-step method by initiating free radicals through a single electron transfer reaction between a photo-excited flavone or coumarin compound and aryl halide, so that the method is simple and efficient, raw materials and reagents are cheap and easy to obtain, the reaction yield is high, few byproducts are produced, and the chemical and regioselectivity of the reaction is high.

Description

technical field [0001] The invention belongs to the field of chemical synthesis methods, and in particular relates to the technical field of a method for synthesizing 3-arylflavones and coumarin compounds induced by light. Background technique [0002] Flavonoids and coumarins are two important types of natural products, which not only have a large number and complex structure, but also have many important pharmacological activities, such as anti-oxidation, anti-cancer, anti-bacterial, anti-viral, anti-coagulant, photosensitizing activities, etc. However, the disadvantages of flavonoids and coumarin natural products such as poor solubility and low bioavailability limit their application in pharmaceutical research. Therefore, it is an important way to rationally develop and utilize flavonoid and coumarin natural products to modify the structure of flavonoid and coumarin natural products with high content in nature to make them meet the requirements of pharmaceutical preparati...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D311/26C07D405/04C07D409/04C07D405/14C07H17/07C07H17/075C07H1/00C07D407/04C07D311/16A61P9/12A61P9/10A61P3/06A61P1/16C09K11/06
CPCC07D311/26C07D405/04C07D409/04C07D405/14C07H17/07C07H17/075C07H1/00C07D407/04C07D311/16A61P9/12A61P9/10A61P3/06A61P1/16C09K11/06C09K2211/1007C09K2211/1088C09K2211/1029C09K2211/1092C09K2211/1044C09K2211/1011
Inventor 夏成峰梁康江纪旭
Owner YUNNAN UNIV
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