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Synthetic method and application of cyanobenzofuran compound

A technology of benzofuran and synthesis method, which is applied in the direction of drug combination, organic chemistry, antineoplastic drugs, etc., can solve the problems of no literature reports, etc., and achieve the effects of good yield, easy price, and simple reaction operation

Inactive Publication Date: 2019-06-07
JISHOU UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0004] So far, there is still no relevant literature report on the conversion of cyanobenzofuran-2-ones to the synthesis of cyanobenzofuran compounds

Method used

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  • Synthetic method and application of cyanobenzofuran compound
  • Synthetic method and application of cyanobenzofuran compound
  • Synthetic method and application of cyanobenzofuran compound

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Embodiment Construction

[0036] The present invention will be further described below in conjunction with specific examples

[0037] Raw material synthesis

[0038] The reaction raw material benzofuran-2-one compound (2a) can be prepared from 2,6-di-tert-butylphenol and benzaldehyde as starting materials, and can be obtained by the following two steps.

[0039]

[0040]

[0041] step one:

[0042] 2,6-Di-tert-butylphenol (10 mmol), benzaldehyde (10 mmol), and 40 mL of dry toluene were successively added to the Dean-Stark device, heated to reflux, and di-n-propylamine (40 mmol) was slowly added dropwise thereto. , keep the temperature unchanged, continue to reflux, and react overnight. When the reaction temperature was lowered to the boiling point of the solvent, 40 mmol of acetic anhydride was added, the solution temperature was continued to be cooled naturally, and the reaction was stirred for 15 min. The reaction solution was poured into 200 mL of ice water, extracted with DCM (3-100 mL),...

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Abstract

The invention discloses a synthetic method of a cyanobenzofuran compound. The synthetic method comprises the following steps: taking a benzofuran-2-ketone compound as a reaction initiator, taking ethyl alcohol as a solvent, slowly adding a reducing agent NaBH4 under a condition of 0 DEG C, then carrying out stirring for a reaction at room temperature, adding water for quenching, extracting the product by using ethyl acetate, then carrying out washing with saturated salt water, collecting the organic layer, carrying out drying and concentrating, carrying out column chromatography or thin-layerchromatography to obtain an intermediate benzofuran-2-ol, taking the benzofuran-2-ol as a raw material, AlCl3 as an additive, and benzene as a solvent to carrying out stirring for a reaction for 2 hours at 60 DEG C in a nitrogen environment, adding water for quenching, extracting the obtained product by using ethyl acetate, collecting the organic layer, carrying out drying and concentrating, and carrying out column chromatography or thin-layer chromatographic separation purification to obtain the target product. The synthesis reaction is simple to operate, the adopted reagents are cheap and are easily available, the reaction system is mild, the conditions are simple, the yield is good, and the method has relatively good popularization and application values.

Description

technical field [0001] The invention relates to a method for synthesizing a cyano group-containing benzofuran compound and its application. Background technique [0002] Benzofuran compounds are the basic skeletons of many drug molecules and have attracted extensive attention due to their remarkable pharmacological and biological activities. Therefore, the synthesis method and research of compounds containing this kind of molecular skeleton can bring great economic benefits and theoretical value. Several benzofuran compounds are shown below, which show important physiological activities, such as anti-infection, for the treatment of vitiligo, psoriasis (psoriasis); such as sedation, for the treatment of insomnia; such as reducing blood uric acid concentration, For the treatment of gout, etc. Therefore, the development of synthetic methods for cyano-containing benzofuran compounds has important practical significance and theoretical basis. [0003] [0004] So far, there...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D307/83A61P35/00
Inventor 唐石余健盛回香王硕文
Owner JISHOU UNIVERSITY
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