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Method for preparing benzopyrone compounds using acetoxy-protected acetylene ketones

A technology of benzopyrone and acetoxy, applied in the field of synthesis of benzopyrone compounds, can solve problems such as long reaction time, achieve short reaction time, wide biological activity and medicinal value, and reaction conditions mild effect

Inactive Publication Date: 2017-07-11
SHAANXI NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Subsequently, people use basic catalysts, such as diethylamine, etc., to catalyze alkyne ketones to prepare benzopyrone compounds. Although this method improves the yield of benzopyrone compounds, the reaction time is longer

Method used

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  • Method for preparing benzopyrone compounds using acetoxy-protected acetylene ketones
  • Method for preparing benzopyrone compounds using acetoxy-protected acetylene ketones
  • Method for preparing benzopyrone compounds using acetoxy-protected acetylene ketones

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0012] Taking the preparation of 2-phenyl-4H-benzopyran-4-one with the following structural formula as an example, the raw materials used and the preparation method are:

[0013]

[0014] Add 0.132g (0.5mmol) of 1-(2-acetoxyphenyl)-3-phenyl-2-ethynyl-1-one and 0.0252g (0.3mmol) of piperazine, 4mL of anhydrous acetonitrile into the Shrek tube , stirred at room temperature for 6 hours, stopped the reaction, and separated by column chromatography to obtain a yellow solid 2-phenyl-4H-benzopyran-4-one with a yield of 95%. The resulting product was characterized by a BrukerAvance type superconducting Fourier digital nuclear magnetic resonance spectrometer, and the characterization data were: 1 H NMR (400MHz, CDCl 3 )δ: 8.24 (d, J = 9.5Hz, 1H), 7.93 (d, J = 8.0Hz, 2H), 7.74-7.67 (m, 1H), 7.56 (dd, J = 18.1, 7.0Hz, 4H), 7.43(t, J=7.5Hz, 1H), 6.84(s, 1H); 13 C NMR (101MHz, CDCl 3 )δ: 178.63, 163.60, 156.45, 133.93, 131.98, 131.76, 129.20, 126.47, 125.89, 125.39, 124.15, 118.24, ...

Embodiment 2

[0016] Taking the preparation of 2-(4-methoxyphenyl)-4H-benzopyran-4-one as an example with the following structural formula, the raw materials used and the preparation method are:

[0017]

[0018] 0.147g (0.5mmol) 1-(2-acetoxyphenyl)-3-(4-methoxyphenyl)-2-ethynyl-1-ketone and 0.0252g (0.3mmol) piperazine, 4mL Anhydrous acetonitrile was added into a Shrek tube, stirred and reacted at room temperature for 3 hours, the reaction was stopped, and column chromatography was separated to obtain a yellow solid 2-(4-methoxyphenyl)-4H-benzopyran-4-one, which The yield is 98%. The resulting product was characterized by a BrukerAvance type superconducting Fourier digital nuclear magnetic resonance spectrometer, and the characterization data were: 1 H NMR (400MHz, CDCl 3 )δ: 8.23(d, J=8.0Hz, 1H), 7.89(d, J=8.8Hz, 2H), 7.68(t, J=7.6Hz, 1H), 7.54(s, 1H), 7.41(t, J=7.5Hz, 1H), 7.03(d, J=8.7Hz, 2H), 6.75(s, 1H), 3.89(s, 3H); 13 CNMR (101MHz, CDCl 3 )δ: 178.68, 163.92, 162.71, 156.72, ...

Embodiment 3

[0020] Taking the preparation of 2-(4-tolyl)-4H-benzopyran-4-one as an example with the following structural formula, the raw materials used and the preparation method are:

[0021]

[0022] 0.139g (0.5mmol) 1-(2-acetoxyphenyl)-3-(4-tolyl)-2-ethynyl-1-one and 0.0252g (0.3mmol) piperazine, 4mL anhydrous acetonitrile Add a Shrek tube, stir the reaction at room temperature for 3 hours, stop the reaction, and separate by column chromatography to obtain a yellow solid 2-(4-methylphenyl)-4H-benzopyran-4-one with a yield of 97%. The resulting product was characterized by a BrukerAvance type superconducting Fourier digital nuclear magnetic resonance spectrometer, and the characterization data were: 1 H NMR (400MHz, CDCl 3 )δ: 8.22(d, J=7.6Hz, 1H), 7.82(d, J=8.1Hz, 2H), 7.68(t, J=8.0Hz, 1H), 7.55(d, J=8.4Hz, 1H) , 7.41(t, J=7.5Hz, 1H), 7.31(d, J=8.1Hz, 2H), 6.79(s, 1H), 2.43(s, 3H); 13 CNMR (101MHz, CDCl 3 )δ: 178.61, 163.75, 156.37, 142.38, 133.78, 129.89, 129.07, 126.35, 125.8...

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Abstract

The invention discloses a method for preparing benzopyrone compounds through adopting acetoxy protected alkynyl ketone. The benzopyrone compounds are generated through a direct ring closure reaction of acetoxy protected alkynyl ketone at room temperature with piperazine as a catalyst. The method has the advantages of simple operation, no need of ligands, low price and small amount of the catalyst, stability of the catalyst to air and water, mild reaction conditions, short reaction time, low cost, high atom economy, extensive substrate applicability, and simple post-treatment and high yield of target products, and can be widely used to prepare natural products benzopyrone compounds.

Description

technical field [0001] The invention belongs to the technical field of synthesis of benzopyrone compounds, and in particular relates to a acetylene compound protected by acetoxy group as a reaction substrate, which is catalyzed by piperazine without adding any ligand. A method for benzopyrone compounds. Background technique [0002] Benzopyrone compounds are natural products widely present in plants and have a wide range of biological activities, such as: antibacterial, antifungal, antiviral, anti-inflammatory, anti-tubulin, etc., and in pharmaceutical intermediates Identified as a preferred structure, which is of great importance in organic synthesis. Therefore, the preparation of benzopyrone compounds has attracted much attention. [0003] In the early days, people used catalyst potassium alkoxide to catalyze alkyne ketones to prepare benzopyrone compounds. The reaction conditions of this method are relatively harsh, and the highest product yield can only reach 78%. Sub...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D311/30C07D311/58C07D409/04
CPCC07D311/30C07D311/58C07D409/04
Inventor 高子伟杨丹丹罗艳龙张伟强郑绍华孙华明张国防
Owner SHAANXI NORMAL UNIV
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