Method for synthesizing selenized benzothiophene compound

A benzothiophene and a synthesis method technology are applied in the field of selenized benzothiophene compounds and their synthesis, and can solve the problems of poor functional group tolerance, complicated operation of selenized benzothiophene compounds and the like, and achieve easy acquisition, wide reaction substrates, Simple post-processing effects

Active Publication Date: 2019-09-20
WENZHOU UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] Technical problem: the first technical problem to be solved by the present invention is the problem of complex operation in the preparation process of selenized benzothiophene compounds
[0007] The second technical problem to be solved by the present invention is the poor tolerance of functional groups in the preparation process of selenized benzothiophene compounds

Method used

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  • Method for synthesizing selenized benzothiophene compound
  • Method for synthesizing selenized benzothiophene compound
  • Method for synthesizing selenized benzothiophene compound

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preparation example Construction

[0036] In the preparation method of the present invention, the reaction temperature is 80°C-130°C, preferably 100°C.

[0037] (4) Response time

[0038] In the preparation method of the present invention, the reaction time is not particularly limited. For example, the appropriate reaction time can be determined by detecting the target product or the residual percentage of the raw material through a gas chromatograph, which is usually 12-24 hours. A non-limiting example is 12 hours, 18 hours, 24 hours, the reaction time is preferably 12 hours.

[0039] In a preferred embodiment, the post-processing step after the reaction can be as follows: after the reaction, the reaction solution is cooled and then filtered with ethyl acetate, concentrated under reduced pressure, and the concentrate is separated by column chromatography (wherein the silica gel 300-400 mesh silica gel), using the mixture of petroleum ether and diethyl ether as the eluent, collecting the eluate, and concentrat...

Embodiment 1

[0043] Synthesis of 2-phenyl-3-(phenylselenyl)benzothiophene

[0044]

[0045] At room temperature, 2-phenylethynyl thioanisole (0.2mmol, 1equiv) of the structure shown in formula 1a, phenylboronic acid (0.4mmol, 2equiv) of the structure shown in formula 2b, selenium powder (0.4mmol, 2equiv) and Silver nitrite (0.04mmol, 0.2equiv) was added to the reaction tube, then pumped and replaced with oxygen three times, 2mL (282mmol) of DMSO was added, and stirred at a reaction temperature of 100°C for 12h. After the end of the reaction was monitored by thin layer chromatography, the reaction mixture was cooled, then diluted with ethyl acetate (the volume ratio of ethyl acetate to the reaction solution was 5:1), concentrated under reduced pressure to obtain a reaction concentrate, and the reaction concentrate was passed through the column Chromatographic separation, using petroleum ether as the eluent, collecting the eluent, spinning off the solvent to obtain the product, the produc...

Embodiment 2

[0052] Synthesis of 2-phenyl-3-(4-chlorophenylselenyl)benzothiophene

[0053]

[0054] At room temperature, 2-phenylethynyl anisole (0.2 mmol, 1 equiv) of the structure shown in formula 1a, 4-chlorophenylboronic acid (0.4 mmol, 2 equiv) of the structure shown in formula 2b-1, selenium powder (0.4 mmol, 2 equiv) and silver nitrite (0.04 mmol, 0.2 equiv) were added to the reaction tube, then pumped and replaced with oxygen three times, 2 mL of DMSO was added, and stirred at a reaction temperature of 100 °C for 12 h. After the end of the reaction was monitored by thin layer chromatography, the reaction mixture was cooled, then diluted with ethyl acetate (the volume ratio of ethyl acetate to the reaction solution was 5:1), concentrated under reduced pressure to obtain a reaction concentrate, and the reaction concentrate was passed through the column Chromatographic separation, using petroleum ether as the eluent, collecting the eluent, spinning off the solvent to obtain the pro...

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Abstract

The invention relates to a method for synthesizing a selenized benzothiophene compound. According to the method, in an organic solvent, under the condition of oxygen, arylboronic acid and selenium powder generate a benzene selenium-based free radical in situ under the action of a silver catalyst, and the benzene selenium-based free radical and alkynyl thioanisole are further subjected to a free radical tandem cyclization reaction to obtain the selenized benzothiophene compound. The present invention further discloses a selenized benzothiophene compound prepared by the method. According to the present invention, the method has characteristics of easily available alkynyl thioanisole as the raw material, inexpensive and easily available elemental selenium, wide reaction substrate range, good functional group tolerance, simple reaction condition and high yield and high purity of product, develops the new synthesis rote and method for selenized benzothiophene compounds, and further 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 selenized benzothiophene compound and a synthesis method thereof. Background technique [0002] The traditional method of synthesizing benzothiophene selenide compounds is mainly catalyzed by some noble metals, such as palladium. [0003] Selenium is an essential nutrient element for animals and a beneficial nutrient element for plants. In recent decades, organoselenium compounds have received increasing attention as a structural framework in many bioactive compounds and medicines. For example, they can be used as antineoplastic, antibacterial, antiproliferative and antibacterial agents. Selenium is also widely used in chiral ligands and materials science. Among them, Professor Zhao Xiaodan from Sun Yat-sen University has made outstanding contributions in the field of chiral selenium-containing ligands. In addition, they are an important synth...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D333/62
CPCC07D333/62
Inventor 周云兵张雪黄阳凤黄小波刘妙昌吴华悦
Owner WENZHOU UNIVERSITY
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