Preparation method of 2-aryl flavone

A technology of aryl flavonoids and hydroxy aryl formic acid, which is applied in the field of preparation of 2-aryl flavonoids, can solve the problems of rare alkynylation reaction and the like, and achieves cheap and easy-to-obtain catalysts, mild reaction conditions and cheap reagents easy-to-get effect

Inactive Publication Date: 2018-06-12
SHAOXING UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Although silver-catalyzed decarboxylation radical reactions have been extended to Hunsdiecker-type halogenation reactions, alkylation, alkenylation, and cyclization reactions, alkynylation reactions are still very rare

Method used

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  • Preparation method of 2-aryl flavone
  • Preparation method of 2-aryl flavone
  • Preparation method of 2-aryl flavone

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1～9

[0030] O-hydroxyarylformylformic acid (1.0mmol, R 1 =H), aryl alkynoic acid (1.1mmol, R 2 =H), silver catalyst (5mol%) and oxidizing agent (2mmol) were dispersed in solvent (2mL), then stirred at 80°C for 3 hours under air atmosphere. After the reaction, with Et 2 O (5 mL) was extracted three times, and the combined organic phases were concentrated under reduced pressure. The obtained crude product was subjected to column chromatography (300-400 mesh silica gel, petroleum ether and ethyl acetate as eluents) to obtain the target product. The types of silver catalysts, oxidants and solvents used and the reaction results are shown in Table 1.

[0031] The reaction condition and reaction result of table 1 embodiment 1~9

[0032]

[0033] a Solvent weight kept at 2mL

Embodiment 10～29

[0035] O-hydroxyarylformylformic acid (1.0mmol), aryl alkynoic acid (1.1mmol), AgNO 3 (5mol%) and K 2 S 2 o 8 (2 mmol) was dispersed in a mixed solvent of acetonitrile (1.5 mL) and water (0.5 mL), and stirred at 80° C. for 3 hours under an air atmosphere. After the reaction, with Et 2 O (5 mL) was extracted three times, and the combined organic phases were concentrated under reduced pressure. The obtained crude product was subjected to column chromatography (300-400 mesh silica gel, petroleum ether and ethyl acetate as eluents) to obtain the target product. The o-hydroxyarylformylformic acid and aryl alkynoic acid used and the reaction results are shown in Table 2.

[0036] The reaction conditions and reaction result of table 2 embodiment 10~29

[0037]

[0038] The characterization data of some products are as follows:

[0039] 2-Phenyl-4H-chromen-4-one(5a): Yellow solid. 1 H NMR (400MHz, CDCl 3 )δ8.25(d,J=7.6Hz,1H),7.97–7.91(m,2H),7.70(t,J=7.6Hz,1H),7.56(dd,J=17.2,...

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Abstract

The invention discloses a preparation method of 2-aryl flavone. The preparation method comprises the following steps: under the action of a silver catalyst and an oxidant, enabling o-hydroxyarylformicacid and aryl acetylenic acid to make ring closing reaction, and after the reaction is ended, performing after-treatment, thus obtaining the 2-aryl flavone. The method disclosed by the invention hasthe advantages of low price of reagents, easiness in obtaining the reagents, mild reaction conditions, good compatibility of reaction functional groups, low price of the catalyst, easiness in obtaining the catalyst, and simple catalytic system.

Description

technical field [0001] The invention belongs to the field of organic synthesis, and in particular relates to a preparation method of 2-aryl flavones. Background technique [0002] As important secondary metabolites of plants, 2-arylflavone derivatives have always been a research hotspot for organic chemists due to their diverse biological activities. In recent years, there has been an upsurge in the development of herbal medicines in the world. Herbal medicines have been favored for their natural and low toxicity, and flavonoids have attracted attention for their broad-spectrum pharmacological effects. Flavonoids exhibit a variety of pharmacological activities, can prevent and treat diseases of the cardiovascular and cerebrovascular systems and respiratory systems, and have pharmacological properties such as anti-inflammatory, antibacterial, hypoglycemic, anti-oxidation, anti-radiation, anti-cancer, anti-tumor, and enhancement of immunity. effect. In recent years, the stud...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D311/30
CPCC07D311/30
Inventor 程凯
Owner SHAOXING UNIVERSITY
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