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Preparation method of flavonoid compound

A technology of flavonoids and carbon atoms, applied in organic chemistry and other fields, can solve the problems of complex and expensive ligands, toxicity, and difficult to guarantee the synthesis yield, and achieve the effects of high reaction efficiency, simple operation, and low cost

Active Publication Date: 2021-06-11
SUN YAT SEN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

These methods use metal catalysis, although they can simplify the synthetic route, but often require noble metals, complex and expensive ligands, toxic reagents, and severe reaction conditions such as high pressure, and the synthetic yield is difficult to guarantee

Method used

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  • Preparation method of flavonoid compound
  • Preparation method of flavonoid compound
  • Preparation method of flavonoid compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0083] The synthesis of 5,7-dimethylflavone, the structural formula is as follows:

[0084]

[0085] Under nitrogen protection, add 4,6-dimethylbenzofuran-2,3-dione (0.2mmol), phenylacetylene (0.3mmol), 1,3-bis(diphenylphosphine) to the reaction flask Ethane (0.01mmol), bis(1,5-cyclooctadiene)nickel (0.01mmol), potassium acetate (0.2mmol) were dissolved in toluene (2mL). The reaction was completed at 120°C under normal pressure for 12 hours. After removing the reaction solvent, the target product 5,7-dimethylflavone was obtained by separation and purification by column chromatography: white solid, 47.6 mg, yield 95%. 1 HNMR (400MHz, CDCl 3 )δ7.91–7.82(m,2H),7.54–7.44(m,3H),7.16(s,1H),6.92(s,1H),6.67(s,1H),2.83(s,3H),2.41 (s,3H); 13 C NMR (101MHz, CDCl 3 )δ180.4, 161.3, 157.8, 143.7, 140.5, 131.8, 131.2, 129.1, 128.9, 126.0, 120.0, 115.9, 108.7, 22.6, 21.6.HRMS(ESI)m / zcalcdfor C 17 h 14 o 2 [M+Na] + 273.0883, found 273.0884.

Embodiment 2

[0086] Embodiment 2: the synthesis of 5,7-dimethylflavone

[0087] Under nitrogen protection, add 4,6-dimethylbenzofuran-2,3-dione (0.2mmol), phenylacetylene (0.3mmol), 1,3-bis(diphenylphosphine) to the reaction flask Propane (0.01 mmol), bis(1,5-cyclooctadiene)nickel (0.01 mmol), were dissolved in toluene (2 mL). The reaction was completed at 120°C under normal pressure for 12 hours. After removing the reaction solvent, the target product 5,7-dimethylflavone was obtained by separation and purification by column chromatography: white solid, 23.5 mg, yield 47%.

Embodiment 3

[0088] Embodiment 3: the synthesis of 5,7-dimethylflavone

[0089] Under nitrogen protection, add 4,6-dimethylbenzofuran-2,3-dione (0.2mmol), phenylacetylene (0.3mmol), 1,3-bis(diphenylphosphine) to the reaction flask Ethane (0.01 mmol), bis(1,5-cyclooctadiene)nickel (0.01 mmol), potassium carbonate (0.2 mmol), were dissolved in toluene (2 mL). The reaction was completed at 120°C under normal pressure for 12 hours. After removing the reaction solvent, the target product 5,7-dimethylflavone was obtained by separation and purification by column chromatography: white solid, 29.5 mg, yield 59%.

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Abstract

The invention belongs to the technical field of organic synthesis, and discloses a preparation method of a flavonoid compound. The preparation method comprises the following steps: taking oxo-isatin or substituted oxo-isatin on a benzene ring, and phenylacetylene or substituted phenylacetylene as reaction substrates, using a nickel catalyst and a ligand as the catalyst, using inorganic base as a cocatalyst, and in a solvent environment, removing carbon monoxide through nickel catalysis, and carrying out cyclization reaction to obtain the flavonoid compound. The method is simple in reaction process operation and low in cost, and does not need strong acid, strong alkali, strong corrosive and toxic reagents; the method also has the advantages of high reaction efficiency, high yield, few byproducts and no need of noble metals and expensive ligands; and meanwhile, the substituent effect of the raw materials has little influence on the reaction, various compounds containing flavone skeletons and having various substitutions and various structures can be synthesized, and the variety of the flavonoid compounds is greatly expanded.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis, in particular to a preparation method of flavonoids. Background technique [0002] Flavonoids widely exist in nature and living organisms, and have a wide range of biological and pharmacological activities, including antioxidant, anticancer, anti-inflammatory, etc., so they are also widely used in medicine and nutrition ((a)Chem .Rev.2014,114,4960-4992; (b)Eur.J.Med.Chem.2014,84,206-239;(c)J.Med.Chem.1990,33,3210-3216;(d)J. Med.Chem.1990, 33, 3216-3222; (e) J.Med.Chem.1992, 35, 3519-3525; (f) J.Med.Chem.2011, 54, 7427-7431; (g) Eur . J. Med. Chem. 2015, 90, 251-257.). The establishment of efficient synthesis methods for such molecules has always been one of the research directions that has attracted much attention in the field of organic synthesis. [0003] The traditional method of constructing flavonoids core is to use ortho-acylphenol compound as substrate, add acid anhydride and ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D311/30
CPCC07D311/30Y02P20/584
Inventor 邱立勤
Owner SUN YAT SEN UNIV
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