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Method for synthesizing flavonoid derivatives

A synthesis method and a derivative technology are applied in the synthesis field of flavonoid derivatives, and achieve the effects of cheap reagents, readily available raw materials and mild reaction conditions

Active Publication Date: 2018-12-07
JIANGXI SCI & TECH NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] In summary, it is particularly important to develop a new synthetic strategy to synthesize flavonoids. So far, the use of o-propargyl phenol as a substrate for the tandem cyclization reaction to prepare flavonoids has not been reported.

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0016] Embodiment 1: the preparation of flavone

[0017] ,

[0018] A representative implementation process: Add o-propargyl phenol to the reaction flask in sequence at room temperature -1 (1.12 g, 5 mmol) and 20 ml of dichloromethane, then hydroiodic acid (1.0 ml, 7.5 mmol) was added into the reaction flask, and then the reaction was placed at 30°C for 1 hour. TLC tracks the progress of the reaction. After the reaction is over, the reaction solution is added to saturated sodium thiosulfate solution, then ethyl acetate is added, and after fully stirring, the layering is allowed to stand; the separated aqueous layer is extracted with ethyl acetate, and the ethyl acetate The extract and the separated organic layer were combined and washed with saturated brine and dried over anhydrous sodium sulfate; the ethyl acetate solvent was evaporated, and then separated and purified by silica gel column chromatography to obtain the intermediate, and then the effluent was placed in a te...

Embodiment 2

[0020] Embodiment 2: Preparation of 4'-methylflavone

[0021] ,

[0022] At room temperature, add o-propargyl phenol to the reaction flask in turn -2 (1.42 g, 5 mmol) and 20 ml of dichloromethane, then hydroiodic acid (1.0 ml, 7.5 mmol) was added to the reaction flask, and then the reaction was placed at 30°C for 1 hour, and the progress of the reaction was tracked by TLC , the separation and purification steps were the same as in Example 1, and 1.18 g of 3',4'-dimethoxyflavone was obtained, with a reaction yield of 83%.

[0023] Pale yellow solid, mp: 108-110℃. 1 H NMR (400 MHz, CDCl 3 ): δ 6.85 (s, 1 H),7.44 (t, J = 7.6 Hz, 1 H), 7.52 – 7.60 (m, 4 H), 7.69 – 7.74 (m, 1 H), 7.93 –7.96 (m, 2 H), 8.23 ​​(d, J = 8.0 Hz, 1 H). 13 C NMR (100 MHz, CDCl 3 ): δ 107.6, 118.1, 124.0, 125.2, 125.7, 126.3, 129.1, 131.6, 131.8, 133.8, 156.3, 163.4, 178.5.

Embodiment 3

[0024] Embodiment 3: Preparation of 4'-chloroflavone

[0025] ,

[0026] At room temperature, add o-propargyl phenol to the reaction flask in turn -3 (1.29 g, 5 mmol) and 20 ml of dichloromethane, then hydroiodic acid (1.0 ml, 7.5 mmol) was added to the reaction flask, and then the reaction was placed at 30°C for 1 hour. TLC followed the progress of the reaction. The separation and purification steps were the same as in Example 1 to obtain 1.17 g of 4'-chloroflavone, and the reaction yield was 91%.

[0027] White solid, mp: 185 - 187°C. 1 H NMR (400 MHz, CDCl 3 ): δ 6.81 (s, 1 H),7.42 – 7.46 (m, 1 H), 7.50 – 7.53 (m, 2 H), 7.56 – 7.59 (m, 1 H), 7.70 – 7.74(m, 1 H) , 7.88 (dd, J = 2.0, 6.8 Hz, 2 H), 8.23 ​​(dd, J = 1.6, 8.0 Hz, 1 H). 13 C NMR (100 MHz, CDCl 3 ): δ 107.7, 118.0, 123.9, 125.4, 125.8, 127.6, 129.4, 130.3, 133.9, 156.2, 162.3, 178.3.

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Abstract

A method for synthesizing flavonoid derivatives comprises: using o-propargyl alcohol phenol as a raw material, adding an organic solvent to fully dissolve the raw material at room temperature, then adding hydriodic acid, reacting at 40 to 60 DEG C for 1 to 2 hours, after the reaction is finished, spin-drying a reaction solution, separating the reaction solution by silica gel column chromatographyto obtain a target effluent, allowing the effluent to stand in a test tube for 1 to 48 hours, and then converting the effluent into flavonoid compounds, wherein the molar ratio of o-propargyl alcoholphenol to hydroiodic acid is 1:1.5 to 2; the organic solvent is a C1-C4 halogenated hydrocarbon or acetonitrile or nitromethane. The method has the characteristics of mild reaction condition, simple operation, simple and easy raw material, high reaction yield, and the like, and is a good synthesis method with good popularization and application prospect.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis and relates to a synthesis method of flavonoid derivatives. Background technique [0002] Flavonoids are one of a very important class of natural products, which widely exist in plants and foods. So far, there are at least 4000 kinds of flavonoids with known chemical structures. This kind of skeleton compound has very important biological activities and pharmacological effects, such as anti-inflammatory, anti-estrogen, antioxidant, anti-cancer agent, anti-AIDS, anti-hypertension, antibacterial, cardiovascular, anti-diabetic, anti-allergy and chemoprevention, etc. effect. In addition, it can also be used as a food additive to make a series of health food. Therefore, it has very important application prospects and theoretical guidance for the synthesis of flavonoids, and has attracted the attention of organic synthesizers and has become one of the important research fields of organic sy...

Claims

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Application Information

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IPC IPC(8): C07D311/30
CPCC07D311/30
Inventor 肖强宋贤荣丁海新李忍
Owner JIANGXI SCI & TECH NORMAL UNIV
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