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A kind of preparation method of benzothiophene derivative

A technology of benzothiophene and derivatives, which is applied in the field of preparation of benzothiophene derivatives, can solve problems such as troublesome operation, waste of raw materials, and environmental pollution, and achieve the effects of easy operation, high economic value, and strong fluorescence performance

Active Publication Date: 2019-07-16
JIAXING UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The method has cumbersome steps, troublesome operation, and a large amount of waste of raw materials, which pollutes the environment and limits the synthesis of such compounds.

Method used

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  • A kind of preparation method of benzothiophene derivative
  • A kind of preparation method of benzothiophene derivative
  • A kind of preparation method of benzothiophene derivative

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1～9

[0022] Add catalyst, sulfur-containing alkynyl compound (II) and organic solvent 2ml in the Schlenk tube of 25ml according to the raw material ratio of Table 1, mix and stir evenly, after the reaction is completed according to the reaction conditions of Table 2, filter, silica gel sample mixing, through Column chromatography (eluent is sherwood oil: ethyl acetate) is purified and obtains corresponding benzothiophene derivative (I), and the reaction process is shown in the following formula:

[0023]

[0024] Table 1

[0025]

[0026] Table 2

[0027]

[0028]

[0029] In Table 1 and Table 2, T is the reaction temperature, t is the reaction time, Me is methyl, OMe is methoxy, DBU is 1,8-diazabicycloundec-7-ene, TBD is 1 ,5,7-Triazabicyclo[4.4.0]dec-5-ene.

[0030] Tested under 365nm fluorescence, the compounds of Examples 1-9 all have higher fluorescence intensity and can be used as potential fluorescent materials. In addition, further functionalization can be car...

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PUM

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Abstract

The invention discloses a preparation method of a benzothiophene derivative. The preparation method comprises the steps of adding a catalyst and a sulfur-containing alkynyl compound into an organic solvent, heating to 40-80 DEG C, and after the reaction is finished, carrying out post-treatment, so as to obtain the benzothiophene derivative. The preparation method of the benzothiophene derivative is easy in operation, simple and convenient in post-treatment, strong substrate designability and relatively strong in practicability, and a compound with a required structure can be designed and synthesized according to actual requirements.

Description

technical field [0001] The invention belongs to the field of organic synthesis, in particular to a preparation method of benzothiophene derivatives. Background technique [0002] Benzothiophene compounds are a very important class of organic intermediates that widely exist in natural products. Common ones are Zileuton, a 5-lipoxygenase inhibitor that inhibits the formation of leukotrienes (LTB4, LTC4, LTD4, and LTE4); Raloxifene, an estrogen Receptor modulator, exhibits antagonistic estrogen effects in uterus and breast tissue, inhibits breast epithelial and endometrial hyperplasia (document: Joshi, E.M., etc., In VitroMetabolism of 2-Acetylbenzothiophene: Relevance to Zileuton Hepatotoxicity. Chemical Research in Toxicology 2004 , 17(2), 137-143). It exhibits excitatory effect on bone fat metabolism and has estrogenic effect (document: Li, H., etc., Drug Design Targeting Protein–Protein Interactions (PPIs) Using Multiple Ligand Simultaneous Docking (MLSD) and Drug Reposit...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D333/64C09K11/06
CPCC07D333/64C09K11/06C09K2211/1007C09K2211/1092
Inventor 姚金忠周宏伟张莲鹏
Owner JIAXING UNIV