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A kind of method of one-pot synthetic benzofuran derivative

A technology for benzofuran and derivatives, applied in the field of one-pot synthesis of benzofuran derivatives, can solve the problems of inappropriate halogen atom-containing benzofuran, limited raw material sources, high price and the like, and achieves low cost and suitable for use. Wide range of effects with high yield and purity

Inactive Publication Date: 2014-10-08
BEIJING NORMAL UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] The most prominent advantage of the above method is that it is versatile, the reaction is simple, and it is a "one-pot" synthesis. However, the sources of raw materials for this method are not extensive. For example, the alkynes used often require multi-step reactions to obtain
In addition, this method also needs to use expensive precious metals such as palladium, which is also one of the bottlenecks that this method is difficult to apply to industrial production.
It should be pointed out that this method is not suitable for the preparation of halogen-containing benzofuran derivatives, especially iodo-containing benzofuran derivatives.

Method used

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  • A kind of method of one-pot synthetic benzofuran derivative
  • A kind of method of one-pot synthetic benzofuran derivative
  • A kind of method of one-pot synthetic benzofuran derivative

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0029] The preparation of embodiment 1,2-(3,4-dimethoxyphenyl) benzofuran

[0030]

[0031] Salicylaldehyde (0.61g, 5mmol), 3,4-dimethoxybenzyltriphenylphosphonium chloride (2.5g, 5.5mmol), potassium hydroxide (0.34g, 6.0mmol) were successively added to 50mL of toluene , Stir the reaction at room temperature (25° C.) until the salicylaldehyde disappears substantially or completely. Add powdered anhydrous potassium carbonate (3.5g, 25.0mmol) to the system and stir for half an hour. If stirring is difficult, add an appropriate amount of toluene or tetrahydrofuran, add iodine (6.4g, 25.0mmol), and stir at room temperature (25°C) until the reaction completely. Add 80 mL of saturated sodium bicarbonate solution to the reaction mixture, add the protective sodium bisulfite solution dropwise until the color of the reaction solution fades, the resulting mixture is extracted with ethyl acetate (3×80 mL), the organic layer is dried over anhydrous sodium sulfate, and the solvent is re...

Embodiment 2

[0033] Example 2, 2-(3-methoxy-4-benzyloxyphenyl)-6-methoxybenzofuran

[0034]

[0035]4-methoxy salicylaldehyde (0.76g, 5mmol), 3-methoxy-4-benzyloxybenzyltriphenylphosphonium chloride (2.9g, 5.5mmol), potassium hydroxide (0.70g, 12.5 mmol) into a thoroughly dried mortar in turn, grind vigorously at room temperature (25°C) for 30 minutes, then grind intermittently for 2 to 3 hours, transfer the resulting paste to a 250mL three-necked reaction flask, and use 20mL tetrahydrofuran (or Toluene) to wash the residue and move it into a reaction flask, add tetrahydrofuran (or toluene) to 50 mL, and stir at room temperature (25° C.) for 2 to 3 hours. Add powdered anhydrous potassium carbonate (3.5g, 25.0mmol) to the system and stir for half an hour. If the stirring is difficult, add an appropriate amount of toluene or tetrahydrofuran, add iodine (6.4g, 25.0mmol), and stir at room temperature (25°C) until the reaction completely. Add 80 mL of saturated sodium bicarbonate solution ...

Embodiment 3

[0041] Example 3, 4-(7-methoxy-2-benzofuryl) methyl benzoate

[0042]

[0043] 3-methoxysalicylaldehyde (0.76g, 5mmol), 4-formylmethylbenzyltriphenylphosphonium chloride (2.5g, 5.5mmol), potassium hydroxide (0.6g, 6.0mmol) were added to In 50 mL of toluene, stir the reaction at room temperature (25° C.) until 3-methoxy salicylaldehyde disappears substantially or completely. Add glacial acetic acid (0.40g, 6mmol) dropwise to the system, add dichlorodicyanobenzoquinone (DDQ) (1.7g, 7.5mmol), and heat to reflux until the reaction is complete. 80mL of saturated sodium bicarbonate solution was added to the reaction mixture, and the resulting mixture was extracted with ethyl acetate (3×80mL), the organic layer was dried over anhydrous sodium sulfate, and the solvent was recovered, and the resulting crude product was purified by column chromatography to obtain the target product 4-(7 -Methoxy-2-benzofuryl)methyl benzoate, yield: 69%.

[0044] The prepared product was a white sol...

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Abstract

The invention relates to a method for synthesizing benzofuran derivatives in a one pot process, which includes the following steps: (1) adding quaternary phosphonium salt or phosphite ester salt and inorganic alkali or organic alkali in salicylaldehyde or salicylaldehyde derivatives, mixing and stirring materials in solvents or leading the materials to be in solid phase and to be grinded for reaction in solvent-free conditions so as to generate 2-styryl phenol derivatives, and (2) adding oxidants into the 2-styryl phenol derivatives obtained through the step (1) in normal position mode for oxidation and cyclization to obtain the benzofuran derivatives. The method has the advantages of being simple and smooth by operating in the one pot process, mild in conditions, easy to magnify, especially suitable for industrial production, wide in application range, high in yield and low in cost.

Description

technical field [0001] The invention relates to the field of preparation of benzofuran derivatives, in particular, the invention relates to a method for synthesizing benzofuran derivatives in one pot. Background technique [0002] Benzofuran and its derivatives are an important class of benzoheterocyclic compounds, which occupy a very important position in natural product chemistry and medicinal chemistry. For example Cicerfuran (I) shows good antibacterial and antifungal effects [Stevenson P.C., Veitch N.C. Phytochemistry, 1998, 48, 995]. Another example is the compound Ailanthoidol (II) isolated from the traditional Chinese medicine Zanthoxylum ailanthoides, which has a wide range of biological activities such as anti-tumor, anti-virus, immunosuppressant, anti-oxidation, anti-fungal and anti-free radical activities [Kao C.L., Chern J.W, J.Org.Chem., 2002, 67, 6772]. In addition, a large number of benzofuran derivatives, such as oleanol [Egonol (III)], Corsifuran C (IV), ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07B41/04C07D307/80C07D307/79C07D409/04C07D407/04C07D493/04C07D307/92
Inventor 段新方廖连燕沈刚段晓峰张雪
Owner BEIJING NORMAL UNIVERSITY