Preparation method of polysubstituted nitrogenous heterocyclic compound

Abstract

The invention discloses a preparation method of a polysubstituted nitrogenous heterocyclic compound. The method comprises the following steps: sequentially adding a nitro compound 1, a methanol solvent and a reducing agent B2(OH)4 into a reaction bottle, putting the reaction bottle into an oil bath pan, carrying out heating and stirring to sufficiently dissolve the mixture, and when detecting thatnitrobenzene is reduced into an amino compound through TCL, stopping the reaction; reducing the temperature of the oil bath pan to normal temperature, and meanwhile, immediately and sequentially adding a keto-aldehyde compound, an isonitrile compound and a carboxylic acid compound into the reaction bottle, adding triethylamine and a toluene solvent; removing the solvents methanol and toluene under reduced pressure after TLC detection reaction is completed, and carrying out column chromatography on the remainder to obtain a target compound, thereby completing the preparation of the benzo nitrogenous heterocyclic compound. According to the technical scheme, based on the Ugi four-component reaction for capturing the amine compounds in situ and the method for synthesizing the nitrogenous heterocyclic compound, direct use of the amine compounds is avoided, and the defects that in the reaction, amine is prone to oxidation, poor in stability and large in harm to the environment are overcome.

Description

technical field [0001] The invention relates to the Ugi-4CR reaction based on capturing amino groups in situ and its application in the synthesis of nitrogen-containing heterocyclic compounds, belonging to the technical field of organic synthesis. Background technique [0002] Nitrogen-containing heterocyclic compounds are an important part of heterocyclic compounds, and they are widely used in many branches of organic chemistry, including active drug research, functional materials, catalysis and coordination chemistry. To expand the scope of such compounds, and to expand their application fields. In addition, nitrogen heterocyclic compounds have an inseparable relationship with life sciences. It has been found clinically that it has a wide range of biological and pharmacological activities and is widely used in the synthesis of drug molecules. Muscle relaxation and stabilizing effects have their own emphasis. This type of drug is well absorbed orally and has a high binding...

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Problems solved by technology

[0003] The patent of the present invention discloses a one-pot synthesis of benzo-nitrogen-containing heterocyclic compounds based on the Ugi-4CR reaction of in-situ capture of amino groups and subsequent series reactions. This method avoids the disadvantages of easy oxidation of amines, poor stability, and great environmental hazards, and solves the Issues such as separation, purification and storage of amines

The in-situ capture method is mostly used to capture active intermediates. Based on our previous research on in-situ capture reactions, we try to develop a green and convenient synthesis method from the perspective of green chemistry to solve the problem of amine compounds in the reaction process. Unfriendliness in

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