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Method for compounding benzofuran derivatives by adding C-O bonds into olefin molecules through non-metallic Lewis acid catalysis

A Lewis acid catalyzed olefin and benzofuran technology, which is applied in organic chemistry and other fields, can solve problems such as transition metal residues, and achieve the effect of avoiding pollution and eliminating post-treatment

Inactive Publication Date: 2018-09-14
NANJING XIAOZHUANG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0004] The purpose of the present invention is to provide a non-metallic Lewis acid-catalyzed intramolecular C-O bonded method of benzofuran derivatives in olefins to solve the problem of transition metal residues caused by the use of transition metal catalysts in the prior art

Method used

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  • Method for compounding benzofuran derivatives by adding C-O bonds into olefin molecules through non-metallic Lewis acid catalysis
  • Method for compounding benzofuran derivatives by adding C-O bonds into olefin molecules through non-metallic Lewis acid catalysis
  • Method for compounding benzofuran derivatives by adding C-O bonds into olefin molecules through non-metallic Lewis acid catalysis

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Experimental program
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Embodiment 1

[0027] The synthesis of benzofuran derivative A in this embodiment includes the following steps:

[0028] (1) Preparation of olefins:

[0029] The reaction formula is:

[0030]

[0031] 12 grams of potassium carbonate, 8.6 mL of methallyl chloride and 7.6 grams of phenol (compound 1) were added to 20.0 mL of acetone solution being stirred, and the resulting mixture was refluxed overnight at room temperature, then 100 mL of water was added, and then Extracted with ether (12 x 10ml). The collected organic layer was washed with 2M NaOH (3x80 mL), washed with MgSO 4 Drying, filtration and concentration in vacuo yielded 4.8 g of intermediate compound 2, which was used without purification.

[0032] 4.8 g of compound 2 was dissolved in 4.0 mL of N,N-dimethylaniline, and the mixture was refluxed at 205° C. for 5 hours in a nitrogen atmosphere. After cooling to room temperature, 400 mL of diethyl ether was added, and the reaction mixture was washed with 1M HCl (3x200 mL). The ...

Embodiment 2

[0040] The synthesis of benzofuran derivative B in this embodiment includes the following steps:

[0041] (1) Preparation of olefins:

[0042] The reaction formula is:

[0043]

[0044] 12 g of potassium carbonate, 8.0 mL of methallyl chloride and 8.0 g of p-methoxyphenol (Compound 1) were added to 16.0 mL of stirred acetone solution, and the resulting mixture was refluxed overnight at room temperature, after which 100 mL of water was added , then extracted with ether (12 x 10ml). The collected organic layer was washed with 2M NaOH (3x80 mL), washed with MgSO 4 Drying, filtration and concentration in vacuo yielded 8.1 g of intermediate compound 2, which was used without purification.

[0045] 8.0 g of intermediate product 2 was dissolved in 35 mL of N,N-dimethylformamide DMF solvent, and the mixture was refluxed at 240 °C for 80 minutes under microwave conditions in a nitrogen atmosphere. Cool to room temperature and concentrate under reduced pressure. The crude produc...

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Abstract

The invention provides a method for compounding benzofuran derivatives by adding C-O bonds into olefin molecules through non-metallic Lewis acid catalysis. The method includes step 1, subjecting raw materials, namely phenol derivatives, to three-step reactions to obtain olefin serving as a reaction substrate; step 2, adding non-metallic Lewis acid and methylbenzene into the reaction substrate obtained in the step 1, and obtaining the benzofuran derivatives after reaction. The method has the advantages that the non-metallic Lewis acid is taken as a catalyst during reaction, so that pollution ofresidual metal catalysts to products is avoided, and troubles in post-treatment are omitted.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis, in particular to a method for synthesizing benzofuran derivatives. Background technique [0002] Benzofuran compounds are a class of natural organic compounds that widely exist in plants, such as in medicinal plants such as Salvia miltiorrhiza, Baibu, wild jasmine, and Zanthoxylum bungeanum. Benzofuran compounds have good antibacterial, antioxidative, antitumor, antiviral and other physiological activities, so they can be used as selective adenosine A1 receptor antagonists, immunosuppressants, etc. However, because the extraction of benzofuran compounds from natural products cannot meet people's needs, it is very important to obtain them by artificial synthesis. [0003] Alkene addition reaction is a very important class of chemical transformation reactions in organic synthesis and medicinal chemistry. The direct addition of C–O bonds to alkenes is a cost-effective method for the func...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D307/79
CPCC07D307/79
Inventor 赵继阳
Owner NANJING XIAOZHUANG UNIV
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