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2-aryl-5-arylselenenyl-1,3,4-oxadiazole compound and preparation method

A technology for oxadiazoles and compounds, which is applied in the field of organic compound synthesis, can solve the problems of complicated operation and poor functional group tolerance, and achieve the effects of high reaction efficiency, simple operation, and simple post-treatment

Active Publication Date: 2017-08-18
WENZHOU MEDICAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0017] The first technical problem to be solved by the present invention is the problem of complicated operation in the preparation process of 2-aryl-5-aryl selenyl-1,3,4-oxadiazole compound
[0018] The second technical problem to be solved by the present invention is the poor tolerance of functional groups in the preparation process of 2-aryl-5-arylselenyl-1,3,4-oxadiazole compounds

Method used

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  • 2-aryl-5-arylselenenyl-1,3,4-oxadiazole compound and preparation method
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  • 2-aryl-5-arylselenenyl-1,3,4-oxadiazole compound and preparation method

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Embodiment 1

[0078] Synthesis of 2-phenyl-5-phenylselenyl-1,3,4-oxadiazole

[0079]

[0080] At room temperature, iodobenzene (1.2mmol, 3equiv), elemental selenium (1.2mmol, 3equiv), 5-phenyl-1,3,4-oxadiazole (0.4mmol, 1equiv), Cu(OAc) 2 (0.04mmol), potassium carbonate (1.2mmol, 3equiv) were added to the reaction tube, then filled with nitrogen, and replaced three times, under nitrogen reaction environment, then added 2mL DMF reaction solvent, stirred at 140 ° C reaction temperature for 24h. After the end of the reaction was monitored by thin-layer chromatography, the reaction mixture was cooled, then diluted with ethyl acetate, the diluted solution was transferred to a separatory funnel, extracted with saturated brine, the aqueous phase and the organic phase were separated, and then diluted with acetic acid Extract the aqueous phase 3 times with ethyl ether, combine the organic phases, add 5g of anhydrous sodium sulfate, stand still for 30min, wash the filter cake with 5mL ethyl acetat...

Embodiment 2

[0089] Synthesis of 2-phenyl-5-(4-methylphenylselenyl)-1,3,4-oxadiazole

[0090]

[0091] At room temperature, 4-methyliodobenzene (1.2mmol, 3equiv), elemental selenium (1.2mmol, 3equiv), 5-phenyl-1,3,4-oxadiazole (0.4mmol, 1equiv), Cu( OAc) 2 (0.04mmol), potassium carbonate (1.2mmol, 3equiv) were added to the reaction tube, then filled with nitrogen, and replaced three times, under nitrogen reaction environment, then added 2mL DMF reaction solvent, stirred at 140 ° C reaction temperature for 24h. After the end of the reaction was monitored by thin-layer chromatography, the reaction mixture was cooled, then diluted with ethyl acetate, the diluted solution was transferred to a separatory funnel, extracted with saturated brine, the aqueous phase and the organic phase were separated, and then diluted with acetic acid Extract the aqueous phase 3 times with ethyl ether, combine the organic phases, add 5g of anhydrous sodium sulfate, stand still for 30min, wash the filter cake w...

Embodiment 3

[0100] Synthesis of 2-phenyl-5-(4-oxyphenylselenyl)-1,3,4-oxadiazole

[0101]

[0102] At room temperature, 4-methoxyiodobenzene (1.2mmol, 3equiv), elemental selenium (1.2mmol, 3equiv), 5-phenyl-1,3,4-oxadiazole (0.4mmol, 1equiv), Cu (OAc) 2 (0.04mmol), potassium carbonate (1.2mmol, 3equiv) were added to the reaction tube, then filled with nitrogen, and replaced three times, under nitrogen reaction environment, then added 2mL DMF reaction solvent, stirred at 140 ° C reaction temperature for 24h. After the end of the reaction was monitored by thin-layer chromatography, the reaction mixture was cooled, then diluted with ethyl acetate, the diluted solution was transferred to a separatory funnel, extracted with saturated brine, the aqueous phase and the organic phase were separated, and then diluted with acetic acid Extract the aqueous phase 3 times with ethyl ether, combine the organic phases, add 5g of anhydrous sodium sulfate, stand still for 30min, wash the filter cake wit...

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Abstract

The invention relates to a 2-aryl-5-arylselenenyl-1,3,4-oxadiazole compound and a preparation method. The preparation method comprises the following steps: in an organic solvent, taking 2-aryl-1,3,4-oxadiazole and aryl iodide as reaction raw materials and taking elemental selenium as an selenylation reagent; carrying out serial reaction under a common promotion effect of a copper catalyst and an alkali to obtain the 2-aryl-5-arylselenenyl-1,3,4-oxadiazole compound. The method provided by the invention has a wide substrate range, simple reaction conditions and relatively high yield and purity of a product; novel synthesis route and method are developed for the 2-aryl-5-arylselenenyl-1,3,4-oxadiazole compound; the method has good application potential and research value.

Description

technical field [0001] The invention belongs to the technical field of organic compound synthesis, and in particular relates to a 2-aryl-5-arylselenyl-1,3,4-oxadiazole compound and a preparation method. Background technique [0002] Selenium has anti-cancer, anti-oxidation, enhances human immunity, antagonizes harmful heavy metals, regulates vitamin absorption, regulates protein synthesis in the human body, and enhances reproductive function. It is also an important component of peroxidase in muscles and seminal plasma. It is recognized by scientists It is called the "king of anti-cancer" of human trace elements. [0003] So far, people have developed a number of drug molecules containing selenoether structures in many specific application fields such as medicine and chemical engineering: Ebselen (Ebselen) is a new type of anti-inflammatory drug developed by Japan's Daiichi Pharmaceutical and Germany's Nattermann, Currently in phase III clinical research; selenium-containin...

Claims

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Application Information

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IPC IPC(8): C07D271/10C07D413/12
CPCC07D271/10C07D413/12
Inventor 吴戈
Owner WENZHOU MEDICAL UNIV
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