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Electrochemical synthesis method of 3-phenylthio quinolinone

A technology of phenylthioquinolinone and synthesis method, which is applied to electrodes, electrolysis process, electrolysis components, etc., can solve the problems of difficult separation and purification, high reaction cost, excess, etc., and achieves easy product separation and purification, and reaction selectivity. High and low cost of raw materials

Active Publication Date: 2020-11-10
HUAIHUA UNIV
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

This method is only suitable for 2-substituted quinolinone substrates, and requires the use of excessive iodine salts, oxidants, and thiophenols, which leads to high reaction costs, difficulty in separation and purification, and safety problems when reacting in large quantities

Method used

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  • Electrochemical synthesis method of 3-phenylthio quinolinone
  • Electrochemical synthesis method of 3-phenylthio quinolinone
  • Electrochemical synthesis method of 3-phenylthio quinolinone

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Experimental program
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Embodiment 1

[0032]

[0033] The specific operation steps are: in a 25mL three-neck round bottom flask, add 4-quinolinone (5mmol), thiophenol (5mmol), sodium iodide (0.5mmol), hexafluoroisopropanol (10mL), 15mm× A 15mm×4mm foam iron electrode is used as an anode, and a 15mm×15mm×4mm foam copper electrode is used as a cathode. The resulting mixed solution was stirred and reacted under 16mA direct current at room temperature for 20 hours. After the reaction was completed, 10mL of water was added to precipitate the product, filtered and dried to obtain the pure product.

[0034] 94%, 3-(phenylthio)quinolin-4(1H)-one

[0035] 1 H NMR (400MHz, CDCl 3 )δ7.08–7.14(m,3H),7.23(t,J=7.8Hz,2H),7.41(t,J=7.8Hz,1H),7.62(d,J=7.8Hz,1H),7.68– 7.72(m, 1H), 8.12(d, J=7.8Hz, 1H), 8.39(d, J=6.0Hz, 1H), 12.32(d, J=5.2Hz, 1H)

[0036] 13 C NMR (100MHz, CDCl 3 ) δ 109.4, 118.5, 124.0, 125.0, 125.1, 125.4, 126.4, 128.9, 132.1, 137.6, 139.8, 145.4, 174.8.

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Abstract

The invention discloses an electrochemical synthesis method of 3-phenylthio quinolinone. The method comprises the following steps: taking a hexafluoroisopropanol solution containing 4-quinolinone, thiophenol and an iodized salt as an electrolytic solution, placing an iron anode and a copper cathode in the electrolytic solution, introducing direct current, and carrying out an electrochemical reaction to obtain 3-thiophenyl quinolinone. The method has the advantages of mild conditions, simple operation, environmental protection, easily available raw materials, high reaction yield and the like.

Description

technical field [0001] The invention relates to an electrochemical synthesis method of 3-phenylthioquinolinone, in particular to a method for oxidative deoxidation of thiophenol and 4-quinolinone catalyzed by iodized salt under the condition of no external oxidant and under the action of direct current. The invention discloses a method for synthesizing 3-phenylthioquinolinone by hydrogen coupling reaction, belonging to the technical field of organic intermediate synthesis. Background technique [0002] 3-Phenylthioquinolinone and its derivatives have a wide range of biological activities and play an important role in the field of drug research and development. There have been many literature reports on the method of using diphenyl disulfide as a vulcanizing agent to synthesize 3-phenylthioquinolinone and its derivatives, but diphenyl disulfide usually needs to be prepared from thiophenol. Such as (Chengcai Xia, Zhenjiang Wei, Yong Yang, Wenbo Yu, Hanxiao Liao, Chao Shen, Pe...

Claims

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Application Information

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IPC IPC(8): C25B3/10C25B11/03C25B11/04
CPCC25B11/04
Inventor 刘益林刘炎云林红卫晏小红张豪张志豪
Owner HUAIHUA UNIV
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