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

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 ...

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.Med.Chem.Lett.2010, 20, 3103) use organometallic reagents (such as Grignard reagents or organic lithium reagents) as arylation Reagent synthesis 3-hydroxyl-3-arylindol-2-one compound, this method is to utilize the stronger nucleophilicity of organometallic reagent, but due to the toxicity of organometallic reagent and the limitation to functional group, and to air and Water sensitivity and other shortcomings limit the widespread use of this method

Images