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Synthesizing method for 3-mercapto indole compound through electrochemical catalytic oxidation

A technology of mercaptoindole and catalytic oxidation, which is applied in the direction of electrolysis process, electrolysis components, electrolysis organic production, etc., can solve the problems of non-progress of reaction and mercaptan peroxidation, and achieve the effect of reducing environmental costs and easy and safe operation

Active Publication Date: 2018-01-23
ZHEJIANG UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, the reaction needs to be carried out at a higher potential, which will easily cause the electropolymerization of indole compounds and the peroxidation of thiols; and the reaction will not proceed basically when aliphatic thiols are used as substrates; Twice as many indole substrates

Method used

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  • Synthesizing method for 3-mercapto indole compound through electrochemical catalytic oxidation
  • Synthesizing method for 3-mercapto indole compound through electrochemical catalytic oxidation
  • Synthesizing method for 3-mercapto indole compound through electrochemical catalytic oxidation

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0025] Embodiment 1: the preparation of 2-methyl-3-phenylthio-1H-indole (formula 1)

[0026] Add 0.1mol / L sodium tetrafluoroborate in acetonitrile solution (15mL), 2-methyl-1H-indole (1mmol), diphenyl disulfide (0.5mmol) and potassium iodide (0.05mmol) into a 30ml beaker . 60°C, constant potential electrolysis at 0.4V, the reaction ends after 6h. The solvent was evaporated under reduced pressure, and then separated by column chromatography, using a mixture of ethyl acetate / n-hexane with a volume ratio of 1:100 as the eluent, the eluate containing the target compound was collected, and the solvent was evaporated to obtain the product 2- Methyl-3-phenylthio-1H-indole. The isolated yield was 94%.

Embodiment 2

[0027] Embodiment 2: the preparation of 2-methyl-3-phenylthio-1H-indole (formula 1)

[0028] The reaction steps were the same as in Example 1, except that the voltage was changed to 0.6V, and the reaction was performed for 5 hours. The isolated yield of 2-methyl-3-phenylthio-1H-indole was 94%.

Embodiment 3

[0029] Embodiment 3: the preparation of 2-methyl-3-phenylthio-1H-indole (formula 1)

[0030] The reaction steps are the same as in Example 1, except that the voltage is changed to 0.2V, and the reaction takes 24 hours. The isolated yield of 2-methyl-3-phenylthio-1H-indole is 90%.

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Abstract

The invention discloses a synthesizing method for a 3-mercapto indole compound through electrochemical catalytic oxidation. According to the method, a three-electrode system is used, a cathode and ananode are graphite electrodes, and a silver nitrate acetonitrile solution of 0.1mol / L is used as a reference electrode; and the indole compounds, disulfide and potassium iodide are added in a sodium tetrafluoroborate acetonitrile solution, stirring and electrolytic reaction are conducted for 3-24h under the condition of the temperature of 45-75 DEG C and 0.2-0.6 V constant voltage, a reaction solution is post-processed, and the product 3-mercapto indole compound is obtained. By means of the synthesizing method, operation is simple, convenient and safe, the yield of the product 3-mercapto indole compound is high, the reaction condition is mild, clean electrical energy is used as a redox agent, and the environmental cost is greatly reduced.

Description

technical field [0001] The invention relates to a method for synthesizing 3-mercaptoindole compounds by electrochemical catalytic oxidation. Background technique [0002] 3-mercaptoindole compounds have very good biological activity and have an irreplaceable role in medicine. Its remarkable therapeutic effect in the treatment of cancer, HIV, allergy, heart disease, bacterial infection, etc. has attracted much attention. In the past ten years, the strategies for synthesizing 3-mercaptoindole compounds can be mainly divided into two types, one is to prepare 3-mercaptoindole compounds through cyclization reaction; the other is to combine indole compounds with sulfur-containing The reaction of nucleophiles to synthesize 3-mercaptoindole compounds. [0003] When using sulfur-containing nucleophiles to react with indole compounds to synthesize 3-mercaptoindole compounds, the main sulfur sources can be divided into the following types: (1) N-arylsulfide phthalimide (2) sulfinic ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C25B3/02C25B3/23
Inventor 李美超沈振陆陈晨
Owner ZHEJIANG UNIV OF TECH
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