Method for synthesizing 3-aryl sulfydryl indole compound

A technology of aryl mercapto indole and synthesis method, which is applied in the field of chemical synthesis of 3-aryl mercapto indole compounds, can solve problems such as application limitation, and achieve the effects of low cost, high reaction selectivity, advanced and reasonable process route

Inactive Publication Date: 2012-07-11
WENZHOU UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Due to these two factors, the application of this method in industrialization is greatly limited.

Method used

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  • Method for synthesizing 3-aryl sulfydryl indole compound
  • Method for synthesizing 3-aryl sulfydryl indole compound
  • Method for synthesizing 3-aryl sulfydryl indole compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0022] Diaryl disulfide, indole compound and N-halogenated succinimide are fed in a molar ratio of 1.0:2.0:2.5, and the diaryl disulfide is diphenyl disulfide, and the feeding quality is 21.8g (0.1mol); The indole compound is indole, and the feeding quality is 23.4g (0.2mol); N-halogenated succinimide is N-bromosuccinimide, and the feeding quality is 44.5g (0.25mol) ; The organic solvent is N,N,-218g of dimethylformamide, and its total consumption is 10 times of the quality of diaryl disulfide.

[0023] Dissolve indole and N-halogenated succinimide in an organic solvent (the amount of organic solvent used is 6 times the mass of diphenyl disulfide). Diaryl disulfide is dissolved in an organic solvent (the amount of organic solvent is 4 times the mass of diphenyl disulfide), slowly added dropwise to the solution of indole compounds and N-halogenated succinimide, The reaction temperature was -15°C, and the reaction was completed after 3 hours.

[0024] After completion of the r...

Embodiment 2

[0027] Diaryl disulfide, indole compound and N-halogenated succinimide are fed in a molar ratio of 1.0:2.0:2.5, and the diaryl disulfide is diphenyl disulfide, and the feeding quality is 21.8g (0.1mol); The indole compound is indole, and the feeding quality is 23.4g (0.2mol); N-halogenated succinimide is N-chlorosuccinimide, and the feeding quality is 33.4g (0.25mol) ; The organic solvent is N,N,-218g of dimethylformamide, and its total consumption is 10 times of the quality of diaryl disulfide.

[0028] The rest are the same as in Example 1, the resulting product 3-phenylmercaptoindole is 22.1g, the yield is 49%, and the purity is 98.8%.

Embodiment 3

[0030] Diaryl disulfide, indole compound and N-halogenated succinimide are fed in a molar ratio of 1.0:2.0:2.5, and the diaryl disulfide is diphenyl disulfide, and the feeding quality is 21.8g (0.1mol); The indole compound is indole, and the feeding quality is 23.4g (0.2mol); N-halogenated succinimide is N-iodosuccinimide, and the feeding quality is 56.3g (0.25mol) ; The organic solvent is N,N,-218g of dimethylformamide, and its total consumption is 10 times of the quality of diaryl disulfide.

[0031] The rest are the same as in Example 1, the resulting product 3-phenylmercaptoindole is 23.9g, the yield is 53%, and the purity is 98.6%.

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Abstract

The invention discloses a method for synthesizing a 3-aryl sulfydryl indole compound which is shown as a formula (I). According to the method for synthesizing the 3-aryl sulfydryl indole compound, an indole compound which is shown as a formula (II) and diaryl disulfides which are shown as a formula (III) are taken as raw materials, and the 3-aryl sulfydryl indole compound is obtained by fully reacting the indole compound and the diaryl disulfides in an organic solvent at the temperature of between -30 and 40 DEG C in the presence of N-halogenate succinimide; and the N-halogenate succinimide is one of N-chlorobutanimide, N-bromosuccinimide, and N-Iodosuccinimide. According to the method, a nonmetal low-toxicity reaction system is used, and cost is low; reaction selectivity and yield are high; a process route is advanced and reasonable, and reaction conditions are mild; and the method has great implementation value and social and economic benefit.

Description

(1) Technical field [0001] The invention relates to a chemical synthesis method of 3-arylmercaptoindole compounds. (2) Background technology [0002] 3-Arylmercaptoindole compounds are a class of compounds with good biological and pharmacological activities, and are widely used in the synthesis of organic compounds and pharmaceutical and chemical intermediates. [0003] In the prior art, a relatively common method is to synthesize 3-arylthioindole compounds through the vulcanization reaction of indole compounds and thiophenols. For example: the method reported in The Journal of Organic Chemistry 2004,69,7688-7693 is to adopt 2,6-di-tert-butyl p-cresol as a free radical inhibitor, and vanadyl acetylacetonate in the presence of potassium iodide and oxygen [ VO(acac) 2 ] Catalyze the vulcanization reaction of indoles and thiophenols. This reaction uses thiophenol which is highly volatile, highly toxic and has a foul smell as a substrate. On the other hand, this method uses a...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D209/30
Inventor 陈久喜吴华悦刘妙昌高文霞
Owner WENZHOU UNIVERSITY
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