Synthetic method of flavonoid compound

A technology of flavonoid compounds and synthetic methods, which is applied in the field of organic synthesis, can solve the problems of aroyl chlorides being sensitive to water vapor, easy to deteriorate and transform, and achieve the effects of convenient process, mild reaction conditions and high yield

Active Publication Date: 2019-09-13
NANJING XIAOZHUANG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, in this synthetic method, aroyl chloride is sensitive to water vapor and easily deteriorated and converted into carboxylic acid. Therefore, the reaction requires anhydrous conditions.

Method used

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  • Synthetic method of flavonoid compound
  • Synthetic method of flavonoid compound
  • Synthetic method of flavonoid compound

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preparation example Construction

[0027] The invention provides a synthesis method of flavonoid compounds. In the synthesis method, high-activity catalyst Co-NC is selected as a catalyst, and oxygen is used as an oxidant to realize efficient and high-selectivity synthesis of flavonoid compounds.

[0028] Specifically, the synthesis method of the present invention is shown in the following formula. Under an oxygen atmosphere, the compound represented by formula A is reacted in a reaction system containing catalyst Co-NC to generate flavonoids represented by formula B. Catalyst Co-NC was prepared by the following method: cobalt salt, terephthalic acid, triethylenediamine were dissolved in DMF (N,N-dimethylformamide), and g-C was added under stirring 3 N 4 (Graphite phase carbon nitride), remove the solvent after the reaction, heat the solid to 850-950°C under an inert atmosphere, preferably to 900°C for 1 hour, and obtain the catalyst Co-NC after cooling. g-C 3 N 4 As a polymer semiconductor, it can be prepar...

Embodiment 1

[0055]

[0056] Under a nitrogen atmosphere, 2.79 mL (22 mmol) of p-methylphenylacetylene, 8.4 mL (2.5 M) of butyllithium n-hexane solution and 30 mL of dry tetrahydrofuran were added to a Schlenk tube, and the mixture was stirred at -78°C for 4 h. 1.91 g (10 mmol) of 3,5-dichlorosalicylaldehyde was added thereto, and stirring was continued at -78°C for 12 h. After the system was cooled to room temperature, 30 mL of saturated ammonium chloride aqueous solution was added to quench the reaction. The mixture was washed with water (3×20 mL), and the resulting aqueous solution was extracted with ether (3×20 mL). Combine the organic phase and ether extract, add 2 g of anhydrous sodium sulfate for drying, and distill off the organic solvent under reduced pressure. The obtained solid residue was separated by column chromatography (petroleum ether: ethyl acetate = 10:1) to obtain 2.46 g of white solid (A-1), with a yield of 80%.

Embodiment 2

[0058]

[0059] Under an oxygen atmosphere, in a sealed tube of 100 mL, add 307.2 mg of substrate A-1 (1 mmol), 15.6 mg of 2,2'-bipyridine (10 mol%), 400 mg of catalyst Co-NC, 15 mL of tetrahydrofuran, and light at room temperature Reaction 12h. After the reaction was finished, the catalyst was left to settle, and the supernatant was transferred into a single-necked round-bottomed flask, and 3×5 mL of dichloromethane was added to wash the catalyst, and the washing liquid was combined into a round-bottomed flask, concentrated under reduced pressure, and subjected to column Chromatographic separation (petroleum ether: ethyl acetate = 10:3) gave 280.8 mg of solid (B-1), with a reaction yield of 92%. The characterization data of solid B-1 are as follows:

[0060] 1 H NMR (CDCl 3 ,300MHz): 8.08(d,J=1.9Hz,1H),7.86(d,J=8.2Hz,2H),7.72(d,J=1.9Hz,1H),7.34(d,J=6.1Hz,2H ), 6.82(s,1H), 2.45(s,3H).

[0061] 13 C NMR (CDCl 3 ,75MHz): 176.5, 163.7, 150.5, 143.0, 133.7, 130.8, 130.0,...

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Abstract

The invention discloses a synthetic method of a flavonoid compound. The synthetic method comprises the following step: in the oxygen atmosphere, a compound as shown in the formula A is subjected to areaction in a reaction system containing a catalyst Co-NC to generate a flavonoid compound as shown in the formula B, wherein R1 and R2 are respectively and individually selected from hydrogen, halogen, cyano group, nitro group, sulfonic group, trifluoromethyl group, amino group, alkyl group having 1 to 12 carbon atoms, alkoxy group having 1 to 12 carbon atoms, alkenyl group having 2 to 12carbon atoms, alkynyl group having 2 to 12 carbon atoms, acyl group having 2 to 12 carbon atoms, aryl group having 6 to 40 carbon atoms, heteroaryl group having 3 to 40 carbon atoms, and a nucleus-fused carbon ring or heterocyclic ring having 3 to 40 carbon atoms; m is an integer selected from 1-4; and n is an integer selected from 1-5. By selecting the catalyst Co-NC with high activity as the catalyst and oxygen as an oxidizing agent in the synthetic method, one-step synthesis of the flavonoid compound under the condition of room temperature is realized. The synthetic method has advantages of mild reaction condition, good selectivity and high yield.

Description

technical field [0001] The invention relates to the technical field of organic synthesis, in particular to a synthesis method of flavonoids. Background technique [0002] Flavonoids (flavonoids) are a class of compounds that exist in nature and have a 2-phenylchromone (flavone) structure. Flavonoids have extensive and important biological activities and pharmacological effects, including: anti-oxidation, anti-inflammatory, anti-cancer, anti-mutagenic, anti-cardiovascular disease and other effects. In recent years, the research on flavonoids has entered a new stage. With the in-depth study of their structure-activity relationship, some mechanisms of pharmacological effects have been discovered, which provides a theoretical basis for their application in the fields of medicine and food. Accelerated the development and utilization of flavonoids. [0003] Recently, the research on the synthesis method of flavonoids has received widespread attention. In the reported synthetic ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D311/30C07D405/04C07D311/92B01J27/24
CPCB01J27/24C07D311/30C07D311/92C07D405/04
Inventor 喻敏刘光祥陈梦然王小锋李健刘少贤郎雷鸣
Owner NANJING XIAOZHUANG UNIV
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