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Method for synthesizing 2-phenyl-3-methylbenzofuran compounds

A synthesis method and technology of benzofuran methyl phenyl ether are applied in the field of synthesis of 2-phenyl-3-methyl benzofuran compounds, can solve the problems of serious environmental pollution, expensive catalyst and the like, and achieve high reaction Yield, wide range of reaction applications, simple and convenient reaction operation

Active Publication Date: 2019-02-26
SHENYANG PHARMA UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0016] The technical problem solved by the present invention is to overcome the shortcomings of expensive catalysts and serious environmental pollution in the prior art, and provide a kind of 3-benzofuran methyl phenyl ether compound as the substrate for the first time without the need for catalysts and solvents by adding Silica gel as an additive can reduce the reaction temperature and increase the reaction yield. A new method for the synthesis of 2-phenyl-3-methylbenzofuran compounds through rearrangement reaction

Method used

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  • Method for synthesizing 2-phenyl-3-methylbenzofuran compounds
  • Method for synthesizing 2-phenyl-3-methylbenzofuran compounds
  • Method for synthesizing 2-phenyl-3-methylbenzofuran compounds

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0030] Substrate 1 (1 mmol) was dissolved in mesitylene (2 mL), the reaction mixture was heated to 180 ° C, and stirred for 4 hours. After the reaction was completed, the target product a was separated by flash column chromatography with a yield of 35 %. Its reaction equation is:

[0031]

[0032] The spectral data of product a is: 1 H NMR (600MHz, CDCl 3 )δ7.46(d, J=7.4Hz, 2H), 7.42(d, J=7.1Hz, 2H), 7.39(t, J=8.4Hz, 5H), 7.33(m, 2H), 7.25(m, 5H), 7.08(d, J=2.2Hz, 1H), 6.97(dd, J=8.5, 2.2Hz, 1H), 6.32(d, J=2.2Hz, 1H), 6.29(d, J=2.2Hz, 1H), 5.93(s,1H), 5.12(s,2H), 5.04(s,2H), 5.02(s,2H), 2.09(s,3H); 13 C NMR (150MHz, CDCl 3 )δ161.7,158.6,157.3,156.7,155.6,143.9,137.1,136.8,136.7,128.8,128.7,128.6,128.3,128.1,127.8,127.7,127.6,127.1,124.1,119.7,115.8,112.2,100.4,97.3,94.7 ,94.2,70.8,70.6,70.30,9.26; HRMS(ESI):m / z:Calcd.for C 36 h 30 o 5 [M+H] + 543.2166, Found 543.2173.

Embodiment 2

[0034] Substrate 1 (1 mmol) was dissolved in toluene (2 mL), ZnCl was added 2 (0.2mmol, 27mg), the reaction mixture was heated to 140°C and stirred for 4 hours. After the reaction was completed, the target product a was separated by flash column chromatography with a yield of 40%. Its reaction equation is:

[0035]

[0036] The spectral data of product a is: 1 H NMR (600MHz, CDCl3 )δ7.46(d, J=7.4Hz, 2H), 7.42(d, J=7.1Hz, 2H), 7.39(t, J=8.4Hz, 5H), 7.33(m, 2H), 7.25(m, 5H), 7.08(d, J=2.2Hz, 1H), 6.97(dd, J=8.5, 2.2Hz, 1H), 6.32(d, J=2.2Hz, 1H), 6.29(d, J=2.2Hz, 1H), 5.93(s,1H), 5.12(s,2H), 5.04(s,2H), 5.02(s,2H), 2.09(s,3H); 13 C NMR (150MHz, CDCl 3 )δ161.7,158.6,157.3,156.7,155.6,143.9,137.1,136.8,136.7,128.8,128.7,128.6,128.3,128.1,127.8,127.7,127.6,127.1,124.1,119.7,115.8,112.2,100.4,97.3,94.7 ,94.2,70.8,70.6,70.30,9.26; HRMS(ESI):m / z:Calcd.for C 36 h 30 o 5 [M+H] + 543.2166, Found 543.2173.

Embodiment 3

[0038] Substrate 1 (1 mmol) was dissolved in dichloromethane (2 mL), silica gel (1 g) was added, dichloromethane was evaporated to dryness by distillation under reduced pressure, the reaction mixture was heated to 140° C., and the reaction was stirred for 4 hours. After the reaction was completed, The target product a was separated by flash column chromatography with a yield of 75%. Its reaction equation is:

[0039]

[0040] The spectral data of product a is: 1 H NMR (600MHz, CDCl 3 )δ7.46(d, J=7.4Hz, 2H), 7.42(d, J=7.1Hz, 2H), 7.39(t, J=8.4Hz, 5H), 7.33(m, 2H), 7.25(m, 5H), 7.08(d, J=2.2Hz, 1H), 6.97(dd, J=8.5, 2.2Hz, 1H), 6.32(d, J=2.2Hz, 1H), 6.29(d, J=2.2Hz, 1H), 5.93(s,1H), 5.12(s,2H), 5.04(s,2H), 5.02(s,2H), 2.09(s,3H); 13 C NMR (150MHz, CDCl 3 )δ161.7,158.6,157.3,156.7,155.6,143.9,137.1,136.8,136.7,128.8,128.7,128.6,128.3,128.1,127.8,127.7,127.6,127.1,124.1,119.7,115.8,112.2,100.4,97.3,94.7 ,94.2,70.8,70.6,70.30,9.26; HRMS(ESI):m / z:Calcd.for C 36 h 30 o 5 [...

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Abstract

The invention provides a method for synthesizing 2-phenyl-3-methylbenzofuran compounds, belonging to the technical field of medicinal chemistry. A general reaction formula is as described in the specification. The reaction substrates of the method are differently-substituted 3-benzofuranmethylphenyl ethers, and reactions are accelerated by stirring and heating under the conditions of no catalyst and no solvent. The reactions can prodoce a series of 2-phenyl-3-methylbenzofuran compounds through rearrangement; and the method of the invention has the characteristics of simple operation, a wide application scope, few by-products, high yield, green reactions, etc.

Description

technical field [0001] The invention belongs to the technical field of medicinal chemistry and relates to a synthesis method of 2-phenyl-3-methylbenzofuran compounds. It specifically relates to a method for generating 2-phenyl-3-methylbenzofuran compounds through rearrangement of 3-benzofuran methyl phenyl ether with specific substitution under the condition of no catalyst and no solvent. Background technique [0002] 2-Phenyl-3-methylbenzofuran is a class of natural products isolated from plants with diverse structures and various activities. Due to its wide range of biological activities, it has attracted the attention of many scientists and can be used as a drug A class of lead compounds developed. A variety of natural products with 2-phenyl-3-methylbenzofuran as the backbone have various biological activities and pharmacological effects, such as antibacterial activity (J.Nat.Prod.2006,69,121-124.), antioxidant activity (Biosci.Biotechnol.Biochem.2001,65,1402-1405.), an...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D307/80
CPCC07D307/80
Inventor 刘永祥程卯生汤迎湛江崇国肖建勇林斌
Owner SHENYANG PHARMA UNIVERSITY
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