Synthesis method for synthesizing 3-sulfonylated thioflavonoid compound

A technology for sulfonylated sulfur and a synthesis method, applied in the direction of organic chemistry and the like, can solve problems such as equipment corrosion and environmental pollution, and achieve the effects of mild reaction conditions, simple and safe operation, and high yield

Active Publication Date: 2020-06-19
ZHENGZHOU UNIV
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0003] The invention provides a synthetic method for synthesizing 3-sulfonylated thioflavonoids to solve the problems o

Method used

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  • Synthesis method for synthesizing 3-sulfonylated thioflavonoid compound
  • Synthesis method for synthesizing 3-sulfonylated thioflavonoid compound
  • Synthesis method for synthesizing 3-sulfonylated thioflavonoid compound

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Embodiment 1

[0031] Add 1-(2-(methylthio)phenyl)-3-phenyl-2-propynyl-1-one (0.2mmol) and phenylsulfonyl hydrazide to the 25mL reaction tube equipped with magnets. (0.4mmol), potassium persulfate (0.4mmol), catalyst 9-s-trimethyl-10-methylacridine perchlorate (0.006mmol); vacuum the reaction tube, replace it with nitrogen three times, and then add the solvent Ethylene glycol (2mL), the reaction tube was irradiated with a blue LED lamp with a wavelength of 460-465nm and stirred at a reaction temperature of 20°C for 12h. After the reaction, water was added to quench the reaction, the reaction solution was extracted with ethyl acetate, and the organic phases were combined and dried over anhydrous sodium sulfate. The target product was obtained by column chromatography. The target product was a white solid with a melting point of 194-195°C. Based on the molar amount of 1-(2-(methylthio)phenyl)-3-phenyl-2-propynyl-1-one as 100%, the yield of the target product was 81%. The structural formula of ...

Embodiment 2

[0038] Add 1-(2-(methylthio)phenyl)-3-(4-methylphenyl)-2-propynyl-1-one (0.2mmol) to the 25mL reaction tube equipped with magnets. , Phenylsulfonyl hydrazide (0.2mmol), potassium persulfate (0.6mmol), catalyst 9-s-trimethyl-10-methylacridine perchlorate (0.002mmol); vacuum the reaction tube and use nitrogen Replace three times, then add solvent ethylene glycol (2mL), and stir the reaction tube for 12h at 10°C under blue light irradiation. After the completion of the reaction, water was added to quench the reaction, the reaction solution was extracted with ethyl acetate, the organic phases were combined and then dried over anhydrous sodium sulfate, and the target product was obtained by column chromatography. The target product was a white solid with a melting point of 150-152°C. Based on the molar amount of 1-(2-(methylthio)phenyl)-3-(4-methylphenyl)-2-propynyl-1-one as 100%, the yield of the target product is 85% . The structural formula of the target product is as follows: ...

Embodiment 3

[0045] Add 1-(2-(methylthio)phenyl)-3-(4-ethylphenyl)-2-propynyl-1-one (0.2mmol) to the 25mL reaction tube equipped with magnets. , Phenylsulfonyl hydrazide (0.4mmol), potassium persulfate (0.2mmol), catalyst 9-s-trimethyl-10-methylacridine perchlorate (0.01mmol); vacuum the reaction tube and use nitrogen It was replaced three times, and then the solvent ethylene glycol (2 mL) was added, and the reaction tube was stirred at 40° C. under blue light irradiation for 18 hours. After the reaction, water was added to quench the reaction, the reaction solution was extracted with ethyl acetate, and the organic phases were combined and dried with anhydrous sodium sulfate. The target product was obtained by column chromatography. The target product was a white solid with a melting point of 159-160 ℃. Based on the molar amount of 1-(2-(methylthio)phenyl)-3-(4-ethylphenyl)-2-propynyl-1-one as 100%, the yield of the target product is 80% , The structural formula of the target product is a...

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Abstract

The invention relates to a synthesis method for synthesizing a 3-sulfonylated thioflavonoid compound. The method comprises the following steps: under the action of a catalyst and an oxidizing agent, putting a methylthio aromatic alkyne ketone compound and an aryl sulfonyl hydrazine compound into a solvent, performing reaction under the conditions of blue light irradiation and a nitrogen environment, and performing separation after the reaction is finished, thereby obtaining the 3-sulfonylated thioflavone compound. According to the method, a transition metal catalyst is not needed, a traditional volatile organic solvent is not needed, a green solvent ethylene glycol or water is used as a reaction medium, an organic photosensitizer is used as a catalyst under the catalysis of visible light,and a target product is synthesized through a one-pot reaction. The method is simple, convenient and safe to operate and mild in reaction condition, the light source used in the method is visible light which is green and pollution-free, the catalyst and the reaction medium are environmentally friendly, and in addition, the yield of the product synthesized by the method is high.

Description

Technical field [0001] The invention relates to the technical field of organic synthesis, in particular to a synthetic method for synthesizing 3-sulfonylated thioflavonoids. Background technique [0002] Thioflavonoids are widely present in many natural products and are important skeletons in many drugs and functional materials. Thioflavonoids have biological activities in antibacterial, anti-tumor and anti-malarial aspects. Therefore, thioflavonoids have attracted much attention in the past few decades. Generally, thioflavonoids can be prepared by the cyclization reaction of methylthio-substituted aromatic alkynone induced by ICl (J.Org.Chem.2006,71,1626); or the addition of sodium sulfide and aromatic alkynone / Cyclization to prepare thioflavonoids (Org. Biomol. Chem. 2010, 8, 90; RSC Adv. 2012, 2, 6549). However, these preparation methods require the use of transition metal catalysts and traditional volatile organic solvents, causing problems such as environmental pollution...

Claims

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Application Information

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IPC IPC(8): C07D335/06
CPCC07D335/06
Inventor 吕琪妍李敬冯志雯宋小杰於兵
Owner ZHENGZHOU UNIV
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