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Catalytic oxidation synthesis method of 3-mercaptoindole compounds

A technology of mercaptoindole and catalytic oxidation, which is applied in the direction of organic chemistry, can solve the problems of DMSO with good hydrophilicity, high boiling point, and unfavorable environmental protection, and achieve the effects of simple and safe operation, mild reaction conditions, and reduced environmental costs

Active Publication Date: 2018-09-28
ZHEJIANG UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] However, the use of DMSO as an oxidizing agent and solvent will have the following defects: (1) DMSO will generate dimethyl sulfide after the reaction, which is unfavorable for environmental protection; trouble

Method used

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  • Catalytic oxidation synthesis method of 3-mercaptoindole compounds
  • Catalytic oxidation synthesis method of 3-mercaptoindole compounds
  • Catalytic oxidation synthesis method of 3-mercaptoindole compounds

Examples

Experimental program
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Effect test

Embodiment 1

[0026] Example 1: Preparation of 3-m-methoxyphenylthio-1H-indole (Formula 1)

[0027] In a 15 mL glass tube, add 3 mL of acetonitrile, 0.5 mmol of 1H-indole, 0.6 mmol of 3-methoxyphenyl sodium thiosulfate, 0.1 mmol of KI, and 0.05 mmol of NaNO 2 , replace the air in the reaction tube with oxygen, seal the bottle mouth with a rubber stopper, insert an oxygen bulb, and then add 0.5mL of HOAc into the reaction tube with a syringe, put the reaction tube into an oil bath preheated to 80°C, and react under stirring 12h. Evaporate under reduced pressure, add sodium thiosulfate solution and stir, then extract with dichloromethane, separate the organic layer, distill off dichloromethane under reduced pressure, and then separate by column chromatography, with ether / petroleum ether volume ratio 1:5 The mixed solution was used as the eluent, and the eluate containing the target compound was collected, and the solvent was evaporated to obtain 3-m-methoxyphenylthio-1H-indole, and the separ...

Embodiment 2

[0028] Embodiment 2: Preparation of 3-m-methoxyphenylthio-1H-indole (formula 1)

[0029] The reaction steps are the same as in Example 1, except that the reaction temperature is changed to 60° C., and the isolated yield of 3-methoxyphenylthio-1H-indole is 70%.

Embodiment 3

[0030] Embodiment 3: Preparation of 3-m-methoxyphenylthio-1H-indole (formula 1)

[0031] The reaction steps are the same as in Example 1, except that acetonitrile is changed to dichloroethane, and the isolated yield of 3-methoxyphenylthio-1H-indole is 55%.

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Abstract

The invention discloses a catalytic oxidation synthesis method of 3-mercaptoindole compounds. The method comprises the following steps: an indole compound and a thiosulfate are used as reaction substrates, potassium iodide and sodium nitrite are used as catalysts, acetic acid is used as an auxiliary agent, oxygen is used as an oxidant, the reaction substrates are subjected to a reaction in an organic solvent under the conditions of normal pressure and temperature of 50-80 DEG C, after the reaction is completed, separation treatment is performed, and therefore one 3-mercaptoindole compound is obtained. The synthetic method disclosed by the invention is simple and safe to operate, and uses the clean oxygen as the terminal oxidant, thereby greatly reducing the environmental costs; and the reaction conditions are mild.

Description

technical field [0001] The invention relates to a catalytic oxidation synthesis method of 3-mercaptoindole compounds. 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 acid; (3) sodium benzen...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D209/30
CPCC07D209/30
Inventor 沈振陆李美超徐超荣易山丽胡宝祥
Owner ZHEJIANG UNIV OF TECH