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Method for preparing benzopyrone compound through adopting pentacarbonyl iron as CO release source

A technology of benzopyrone and iron pentacarbonyl, applied in the direction of organic chemistry, etc., to achieve the effect of reducing the harsh requirements of reaction equipment, easy control, and mild reaction conditions

Inactive Publication Date: 2017-05-10
SHAANXI NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] The technical problem to be solved by the present invention is to overcome the shortcomings of the existing preparation methods of benzopyrone compounds, and provide a CO supply source without adding ligands, mild reaction conditions, short reaction time, single reaction product, and safety Preparation method of benzopyrone compounds with high efficiency and high yield

Method used

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  • Method for preparing benzopyrone compound through adopting pentacarbonyl iron as CO release source
  • Method for preparing benzopyrone compound through adopting pentacarbonyl iron as CO release source
  • Method for preparing benzopyrone compound through adopting pentacarbonyl iron as CO release source

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0012] Preparation of 2-phenyl-4H-benzopyran-4-one with the following structural formula

[0013]

[0014] 0.11g (0.5mmol) 2-iodophenol, 72μL (0.75mmol) phenylacetylene, 0.0056g (0.025mmol) palladium acetate, 0.1293g (1.5mmol) piperazine and 30μL (0.15mmol) pentacarbonyl iron, 3mL anhydrous Add acetonitrile into the Shrek tube, stir and react at 50°C for 12 hours, stop the reaction, cool down to room temperature naturally, and separate by column chromatography to obtain a yellow solid 2-phenyl-4H-benzopyran-4-one with a yield of 95%, the structural characterization data is: 1 H NMR (400MHz, CDCl 3 )δ8.24(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, 107.78, 100.13.

Embodiment 2

[0016] Preparation of 2-(4-methoxyphenyl)-4H-benzopyran-4-one with the following structural formula

[0017]

[0018] In Example 1, the phenylacetylene used was replaced with equimolar 4-methoxyphenylacetylene, and other steps were the same as in Example 1 to obtain a yellow solid 2-(4-methoxyphenyl)-4H-benzopyridine Furan-4-one, its yield is 94%, and structural characterization data is: 1 H NMR (400MHz, CDCl 3 )δ8.23(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 C NMR (101MHz, CDCl 3 )δ 178.68, 163.92, 162.71, 156.72, 133.70, 128.16, 125.83, 125.23, 124.21, 124.11, 118.10, 114.63, 106.36, 100.13, 55.65.

Embodiment 3

[0020] Preparation of 2-(4-tolyl)-4H-benzopyran-4-one with the following structural formula

[0021]

[0022] In Example 1, the phenylacetylene used was replaced with an equimolar 4-methylphenylacetylene, and other steps were the same as in Example 1 to obtain a yellow solid 2-(4-methylphenyl)-4H-benzopyran-4- Ketone, its yield is 94%, and structural characterization data is: 1 HNMR (400MHz, CDCl 3 )δ8.22(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 C NMR (101MHz, CDCl 3 ) δ 178.61, 163.75, 156.37, 142.38, 133.78, 129.89, 129.07, 126.35, 125.80, 125.25, 124.11, 118.17, 107.09, 21.65.

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Abstract

The invention discloses a method for preparing a benzopyrone compound through adopting pentacarbonyl iron as a CO release source. The method comprises the step of subjecting a 2-iodophenol compound and terminal alkyne to a coupling reaction under mild conditions in a manner of taking palladium acetate as a catalyst, taking piperazine as a base and taking the pentacarbonyl iron as the CO release source, so as to produce the benzopyrone compound. According to the method, the operation is simple, the reaction conditions are mild, the consumption of the catalyst is low, the consumption of the CO release source is low, the toxicity is relatively low, the cost is relatively low, the substrate applicability is high, and the yield of target object is high, so that the method can be extensively applied to the preparation of a natural product, i.e., the benzopyrone compound.

Description

technical field [0001] The invention belongs to the technical field of synthesis of benzopyrone compounds, and specifically relates to a method that uses iron pentacarbonyl as a carbon monoxide (CO) release source and 2-iodophenol compounds as a reaction substrate without adding any ligands. A method for synthesizing benzopyrone compounds under the conditions of using palladium acetate as a catalyst and piperazine as a base. 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, adopting a simple method to prepare benzopyrone compounds has attracted much attention in the organic and pharmaceutical fields. [0003] In the early days, CO gas was used as the carbonyl su...

Claims

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Application Information

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IPC IPC(8): C07D311/30C07D409/04
CPCC07D311/30C07D409/04
Inventor 高子伟杨丹丹徐珊张伟强郑绍华孙华明张国防
Owner SHAANXI NORMAL UNIV
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