Benzothiophene compound as well as preparation method and application method thereof

A technology of benzothiophene and an application method, which is applied in the field of heterocyclic compound synthesis, can solve the problems of high environmental hazard of halogen-containing waste liquid, does not conform to green chemistry, harsh reaction conditions, etc., achieves good scalability, reduces synthesis cost, and reacts The effect of fewer steps

Inactive Publication Date: 2020-09-18
SHAOXING UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0004] Wherein, the method for preparing benzothiophene compounds through intramolecular cyclization of o-alkynylthiophenol (thioether) mainly includes: 1. using Pd / Cu as a catalyst, through I 2 、Br 2 , NBS, p-O 2 NC 6 h 4 SCl or PhSeCl carry out electrophilic cyclization to prepare benzothiophene compound, and this method condition is mild, and yield is high, but the halogen-containing waste liquid that produces is bigger to environmental hazards, does not accord with the concept of green chemistry; ② with Au(I) -IPr is used as a catalyst to prepare benzothiophene compounds through cyclization reaction. This method has good substrate adaptability, but the catalyst is expensive and the reaction conditions are relatively harsh; Cyclization reaction to prepare benzothiophene compounds, this method can simultaneously build multiple chemical bonds to obtain benzothiophene derivatives with various structures, but this type of reaction has poor selectivity, many by-products, and low yield

Method used

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  • Benzothiophene compound as well as preparation method and application method thereof
  • Benzothiophene compound as well as preparation method and application method thereof
  • Benzothiophene compound as well as preparation method and application method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0047] Embodiment 1: Preparation of benzothiophene compound 1

[0048] 2-Phenylethynylanisole sulfide (44.8mg, 0.2mmol), DTPB (117.0mg, 0.8mmol), disodium hydrogen phosphate (283.9mg, 0.2mmol), acetone (2mL), Under the protection of nitrogen, raise the temperature to 130°C and stir the reaction for 24 hours, extract with 2x8mL dichloromethane, combine the organic phases, dry overnight with anhydrous sodium sulfate or anhydrous magnesium sulfate, spin dry, and pass through the column with petroleum ether: ethyl acetate = 2:1 , to obtain 36.2 mg of the target compound as a white solid, with a yield of 68%.

[0049] Product structure verification (see attached Figures 1A-1B ):

[0050] 1 H NMR (δ, ppm, 400MHz, CDCl 3 ):δ7.86(dd,J=7.4,1.6Hz,1H),7.60(dd,J=7.4,1.6Hz,1H),7.52–7.42(m,5H),7.42–7.34(m,2H), 3.96(s,2H),2.14(s,3H);

[0051] 13 C NMR (δ, ppm, 100MHz, CDCl 3 ): δ206.2, 141.5, 140.0, 139.0, 133.9, 129.6, 128.8, 128.5, 124.8, 124.65, 124.62, 122.3, 122.0, 42.5, 29.4. ...

Embodiment 2

[0052] Embodiment 2: the selection of free radical initiator consumption

[0053] The experimental conditions and feeding amount of this embodiment are the same as those in Example 1, and different amounts of free radical initiators are selected for experimentation, as shown in Table 1.

[0054] The reaction result of the free radical initiator of different consumptions of table 1

[0055]

[0056]

[0057] It can be seen from Table 1 that the reaction effect and yield of DTPB in an amount of 4-6 equiv are better, and the amount of DTPB is preferably 4 equiv in comprehensive consideration.

Embodiment 3

[0058] Embodiment 3: the selection of disodium hydrogen phosphate consumption

[0059] The experimental conditions and the feeding amount of this embodiment are the same as those in Example 1, and different amounts of disodium hydrogen phosphate are selected for the experiment, as shown in Table 2.

[0060] Table 2 Na in different amounts 2 HPO 4 The result of the reaction

[0061] serial number Na 2 HPO 4 (x equiv)

[0062] It can be seen from Table 2 that the reaction effect and yield of disodium hydrogen phosphate in an amount of 1 to 4 equiv are better, and 1 equiv is preferred in comprehensive consideration.

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Abstract

The invention provides a benzothiophene compound as well as a preparation method and an application method thereof, and belongs to the technical field of heterocyclic compound synthesis. The preparation method comprises the following steps: taking acetone as a solvent, DTPB as a free radical initiator and a 2-ethynylphenylthioether derivative as a raw material, carrying out a one-step reaction ina nitrogen atmosphere in the presence of sodium dihydrogen phosphate to prepare a crude product, and refining the crude product to obtain the benzothiophene compound. The prepared compound is a new compound, the steps are short, the operation is simple, the cost is low, and a universal new method is provided for the preparation of benzothiophene compounds.

Description

technical field [0001] The application relates to a benzothiophene compound and a preparation and application method thereof, belonging to the technical field of synthesis of heterocyclic compounds. Background technique [0002] Benzothiophene and its derivatives are one of the aromatic heterocyclic compounds containing sulfur atoms, and their derivatives are widely used in medicine, dyes, new polymers and luminescent materials. In terms of medicine, drugs with benzothiophene as the pharmacophore include brepiprazole, ipagliflozin L-proline salt, sertaconazole nitrate, etc.; at the same time, benzothiophene derivatives can also be used to synthesize New materials such as liquid crystal polymers and superconductors are a new type of organic photoelectric materials, which have good application prospects in the field of organic electronic materials such as new batteries. For example, S, S-dioxy-dibenzothiophene is a good Luminescent material. However, the reaction of benzothi...

Claims

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Application Information

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IPC IPC(8): C07D333/56C07D409/04C07D495/04A61K31/381A61K31/4436A61K31/4365A61P17/00A61P31/10
CPCA61P17/00A61P31/10C07D333/56C07D409/04C07D495/04
Inventor 徐慧婷蔡涛吴春雷沈润溥盛国栋高晓忠
Owner SHAOXING UNIVERSITY
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