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5-substituted sulfur etherified/selenium etherified/tellurium etherified quinoline compound and preparation method therefor

A technology of compounds and quinolines, applied in the field of catalytic organic synthesis, can solve the problems of difficult control of selectivity, many steps, and rare

Active Publication Date: 2015-12-23
HUNAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, this method requires pre-preparation of expensive multi-substituted precursor aniline, many steps, complicated operation, and sometimes the selectivity is difficult to control
There are very few reports on the selective modification of the existing quinoline core structure to synthesize the corresponding quinoline derivatives

Method used

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  • 5-substituted sulfur etherified/selenium etherified/tellurium etherified quinoline compound and preparation method therefor
  • 5-substituted sulfur etherified/selenium etherified/tellurium etherified quinoline compound and preparation method therefor
  • 5-substituted sulfur etherified/selenium etherified/tellurium etherified quinoline compound and preparation method therefor

Examples

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Effect test

preparation example 1

[0022] Add 0.25 mmol 8-(trimethylacetamido) quinoline (R 1 =tert-butyl), 0.3mmol diphenyl disulfide (R 2 =Ph), CuBr 2 0.025mmol and 1mL DMF, under nitrogen atmosphere, the reaction was carried out at 160°C for 24h. After the reaction was completed, it was filtered, concentrated, and separated by column chromatography to obtain 5-phenylmercapto-8-(trimethylacetylamino)quinoline with a yield of 10%.

preparation example 2

[0024] Add 0.25 mmol 8-(trimethylacetamido) quinoline (R 1 =tert-butyl), 0.3mmol diphenyl disulfide (R 2 =Ph), CuCl 2 0.025mmol and 1mL DMF, under nitrogen atmosphere, the reaction was carried out at 160°C for 24h. After the reaction was completed, it was filtered, concentrated, and separated by column chromatography to obtain 5-phenylmercapto-8-(trimethylacetylamino)quinoline with a yield of 7%.

preparation example 3

[0026] Add 0.25 mmol 8-(trimethylacetamido) quinoline (R 1 =tert-butyl), 0.3mmol p-tert-butylphenyl disulfide (R 2 =4-tert-Ph), CuI0.025mmol and 1mL DMF, under nitrogen atmosphere, the reaction was carried out at 160°C for 24h. After the reaction was completed, it was filtered, concentrated, and separated by column chromatography to obtain 5-(4-tert-butylphenylmercapto)-8-(trimethylacetamido)quinoline with a yield of 8%.

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Abstract

The invention relates to a 5-substituted sulfur etherified / selenium etherified / tellurium etherified quinoline compound and a preparation method therefor. The preparation method is characterized by comprising: carrying out a reaction at a certain temperature for a certain time to obtain the 5-substituted sulfur etherified / selenium etherified / tellurium etherified quinoline compound with a high yield and high selectivity by taking quinoline, diaryl(alkyl) disulfide (R2SSR2) or diaryl(alkyl) diselenide (R2SeSeR2) or diaryl(alkyl) ditelluride (R2TeTeR2) as raw materials, copper salt that is low in price and is easily available as a catalyst and a common oxidant as an oxidant and a common organic solvent as a reaction solvent. The method has the advantages of being relatively low in cost, high in yield, simple to operate, less in pollution and the like, and has certain feasibility for realizing industrial production.

Description

【Technical field】 [0001] The invention belongs to the field of catalytic organic synthesis, and in particular relates to a 5-position substituted thioetherified / selenoetherified / tellurified quinoline compound and a preparation method thereof. 【Background technique】 [0002] Due to their important role in natural products and pharmaceutical industry, quinolines have been widely concerned by chemical researchers in recent years. The introduction of thioether structure (-SR) or selenoether structure (-SeR) or telluride (-TeR) makes the compound have special activity and has a great prospect of medicinal value. Since the last century, many classic synthetic methods have been reported one after another. At present, the more common method is to use precursor aniline and carbonyl compound or alkyne to carry out cycloaddition reaction and ring closure to prepare corresponding quinoline compounds. However, this kind of method requires pre-preparation of expensive multi-substituted ...

Claims

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Application Information

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IPC IPC(8): C07D215/40
CPCC07D215/40
Inventor 邱仁华朱龙志曹鑫尹双凤雷健
Owner HUNAN UNIV
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