Method for synthesizing 3-hydroxy-3-arylindole-2-one derivative

A synthesis method and derivative technology, applied in the field of chemical synthesis of 3-hydroxy-3-arylindol-2-one derivatives, can solve the problems of strict structure requirements, difficulty in obtaining, expensive catalysts, etc., and achieve product quality Good, cheap, large implementation value and the effect of social and economic benefits

Inactive Publication Date: 2012-05-02
WENZHOU UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] In the prior art, some (such as: Angew.Chem.Int.Ed.2011, 50, 7620) use intramolecular cyclization to synthesize 3-hydroxyl-3-arylindol-2-one derivative compounds, which The method is to use a metal palladium catalyst to form a ring structure, which has strict requirements on the structure of the reaction substrate and is difficult to obtain, and the catalyst used is relatively expensive
Some (such as J.Am.Chem.Soc.2004, 126, 12888 and Bioorg.

Method used

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  • Method for synthesizing 3-hydroxy-3-arylindole-2-one derivative
  • Method for synthesizing 3-hydroxy-3-arylindole-2-one derivative
  • Method for synthesizing 3-hydroxy-3-arylindole-2-one derivative

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0024] N-methyl isatin, phenylboronic acid, copper trifluoromethanesulfonate, o-phenanthroline monohydrate, and lithium hydroxide monohydrate are charged at a material ratio of 1.0:2.0:0.05:0.1:3.0, and N-methyl Isatin 16.1g (0.1mol); Phenylboronic acid 24.4g (0.2mol); Copper trifluoromethanesulfonate 1.8g (0.005mol); O-phenanthroline monohydrate 2.0g (0.01mol); Lithium hydroxide monohydrate 12.6 g (0.3mol); Organic solvent is xylene 241.5g, and its total consumption is 15 times of N-methyl isatin quality.

[0025] Put N-methylisatin, phenylboronic acid, copper trifluoromethanesulfonate, phenanthroline monohydrate, and lithium hydroxide monohydrate into the reaction kettle, add xylene to dissolve, the reaction temperature is 100°C, and react after 48 hours Finish.

[0026] After the reaction, the organic solvent was recovered by distillation under reduced pressure, and the solid remaining in the reaction flask was recrystallized from ethanol dried with calcium chloride to obt...

Embodiment 2

[0029] N-methylisatin, phenylboronic acid, copper trifluoromethanesulfonate, 4,4'-dimethyl-2,2'-bipyridine, and lithium hydroxide monohydrate have a material ratio of 1.0:2.0:0.05 : 0.1: 3.0 feeding, N-methylisatin 16.1g (0.1mol); phenylboronic acid 24.4g (0.2mol); copper trifluoromethanesulfonate 0.92g (0.005mol); 4,4'-dimethyl- 2,2'-bipyridine 2.08g (0.01mol); Lithium hydroxide monohydrate 12.6g (0.3mol); The organic solvent is 241.5g xylene, the total amount of which is 15 times the mass of N-methylisatin.

[0030] The rest are the same as in Example 1, and the obtained product N-methyl-3-hydroxyl-3-phenylindol-2-one is 11.9 g, the yield is 50%, and the purity is 98.5%.

Embodiment 3

[0032] N-methyl isatin, phenylboronic acid, copper trifluoromethanesulfonate, o-phenanthroline monohydrate, and cesium carbonate are charged with a material ratio of 1.0: 2.0: 0.05: 0.1: 3.0, N-methyl isatin 16.1 g (0.1mol); 24.4g (0.2mol) of phenylboronic acid; 1.8g (0.005mol) of copper triflate; 2.0g (0.01mol) of phenanthroline monohydrate; 97.8g (0.3mol) of cesium carbonate; Organic solvent is xylene 241.5g, and its total consumption is 15 times of N-methyl isatin quality.

[0033] The rest are the same as in Example 1, and the obtained product N-methyl-3-hydroxyl-3-phenylindol-2-one is 13.9 g, the yield is 58%, and the purity is 98.4%.

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Abstract

The invention discloses a method for synthesizing a 3-hydroxy-3-arylindole-2-one derivative shown as a structural formula (I), which comprises the following steps of: fully reacting raw materials such as an isatin compound shown as a structural formula (II) and arylboric acid shown as a structural formula (III) in an inert organic solvent in the presence of a copper catalyst, a nitrogen-containing bidentate ligand and an alkaline compound, and separating and purifying reaction liquid after the reaction is finished to obtain the 3-hydroxy-3-arylindole-2-one derivative, wherein the copper catalyst is one or any combination of copper trifluoromethanesulfonate, copper acetylacetonate, copper acetate, cuprous iodide, copper bromide, copper fluoride and copper chloride. The method is high in implementation value and good in social benefit and economic benefit.

Description

(1) Technical field [0001] The invention relates to a chemical synthesis method of 3-hydroxy-3-arylindol-2-one derivatives. (2) Background technology [0002] 3-Hydroxy-3-arylindol-2-one compounds are a class of compounds with good biological activity and pharmacological activity, which are widely used in the synthesis of pesticides and medicines, and have high practical value. It plays an active role in anti-cancer, anti-inflammatory, and treatment of blood diseases. [0003] In the prior art, some (such as: Angew.Chem.Int.Ed.2011, 50, 7620) use intramolecular cyclization to synthesize 3-hydroxyl-3-arylindol-2-one derivative compounds, which The method is to use a metal palladium catalyst to form a ring structure, which has strict requirements on the structure of the reaction substrate and is difficult to obtain, and the catalyst used is relatively expensive. Some (such as J.Am.Chem.Soc.2004, 126, 12888 and Bioorg.Med.Chem.Lett.2010, 20, 3103) use organometallic reagents ...

Claims

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Application Information

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IPC IPC(8): C07D209/38
Inventor 陈久喜刘妙昌高文霞张吉磊吴华悦
Owner WENZHOU UNIVERSITY
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