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Method for synthesizing 5-substituted barbituric acid derivative under catalysis of rare earth chloride

A rare earth chloride, barbituric acid technology, applied in the direction of organic chemistry, can solve the problems of many side reactions, harsh reaction conditions, low yield, etc., to achieve good substrate universality, simple synthesis method, and easy application Effect

Inactive Publication Date: 2019-12-20
SHANGHAI URBAN CONSTR VOCATIONAL COLLEGE
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0003] The traditional synthesis method of this type of compound is realized by condensation reaction of malonate derivatives and urea under the action of strong base sodium alkoxide, but the reaction conditions are harsh, usually requiring conditions such as inert gas protection, high temperature and anhydrous solvent , and there are many side reactions, the yield is not high, and the product separation is difficult; there is also a method that Lam reported is the noble metal-catalyzed reaction of aromatic hydrocarbons and diazo compounds, but this reaction uses noble metal catalysts, and the cost is high. In addition, diazo compounds The stability is not good enough and has certain limitations

Method used

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  • Method for synthesizing 5-substituted barbituric acid derivative under catalysis of rare earth chloride
  • Method for synthesizing 5-substituted barbituric acid derivative under catalysis of rare earth chloride
  • Method for synthesizing 5-substituted barbituric acid derivative under catalysis of rare earth chloride

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0024]

[0025] Add 1.0mmol of 1,3-dimethylbarbituric acid, 1.0mmol of methyl iodide, and catalyst yttrium trichloride YCl to the reaction tube in sequence. 3 0.05 mmol, and 2 mL of solvent methanol was added, and the reaction was carried out at room temperature for 8 hours. After the reaction, the reaction solution was concentrated and separated by column chromatography to obtain the corresponding product with an isolation yield of 87%. 1 H NMR (400MHz, CDCl 3 ) δ: 4.78-4.72 (m, 1H), 3.40 (s, 6H), 1.05 (d, J=6.2Hz, 3H). HRMS theoretical value C 7 h 11 N 2 o 3 (M+H) + : 171.0770, actual measured value: 171.0775.

Embodiment 2

[0027]

[0028] Add 1.0mmol of 1,3-dimethylbarbituric acid, 1.2mmol of ethyl bromide, catalyst YbCl 3 0.02 mmol, and 2 mL of solvent methanol was added, and the reaction was carried out at room temperature for 6 hours. After the reaction, the reaction solution was concentrated and separated by column chromatography to obtain the corresponding product with an isolation yield of 85%. 1 H NMR (400MHz, CDCl 3 ) δ: 4.75(t, J=5.8Hz, 1H), 3.42(s, 6H), 1.09-1.05(m, 2H), 0.95(t, J=6.0Hz, 3H). HRMS theoretical value C 8 h 13 N 2 o 3 (M+H) + : 185.0926, actual measured value: 185.0930.

Embodiment 3

[0030]

[0031] Add 1.0mmol of 1,3-dimethylbarbituric acid, 1.2mmol of bromobenzene, catalyst ytterbium trichloride YbCl in the reaction tube 3 0.05 mmol, and 2 mL of solvent ethanol was added, and the reaction was carried out at room temperature for 10 hours. After the reaction, the reaction solution was concentrated and separated by column chromatography to obtain the corresponding product with an isolation yield of 90%. 1 H NMR (400MHz, CDCl 3 ) δ: 7.41-7.34 (m, 3H), 7.23 (dd, J=7.4, 1.8Hz, 2H), 4.67 (s, 1H), 3.36 (s, 6H). HRMS theoretical value C 12 h 13 N 2 o 3 (M+H) + : 233.0926, actual measured value: 233.0922.

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Abstract

The invention belongs to the technical field of synthetic chemistry, and particularly relates to a method for synthesizing a 5-substituted barbituric acid derivative under the catalysis of a rare earth chloride. The preparation method comprises: dissolving a halogenated hydrocarbon and 1,3-dimethyl barbituric acid in an organic solvent, carrying out a reaction for 6-10 h at a room temperature by using a rare earth chloride as a catalyst, and separating and purifying to obtain the 5-substituted barbituric acid derivative. According to the invention, the method has characteristics of simple andenvironmentally-friendly synthesis process, excellent selectivity, high yield and wide substrate range, and further has wide application value in the fields of biology, pharmaceutical chemistry industry and the like.

Description

technical field [0001] The invention relates to the technical field of chemical synthesis, in particular to a method for catalytically synthesizing 5-substituted barbituric acid derivatives with rare earth chlorides. Background technique [0002] Barbituric acid derivatives are a class of compounds with nitrogen-containing heterocyclic skeletons. These compounds usually have strong physiological activities and have important applications in the fields of biology, medicine and chemical industry. Among them, the 5-substituted barbituric acid derivatives It has potential sedative, hypnotic, immune regulation and anti-tumor functions. [0003] The traditional synthesis method of this type of compound is realized by condensation reaction of malonate derivatives and urea under the action of strong base sodium alkoxide, but the reaction conditions are harsh, usually requiring conditions such as inert gas protection, high temperature and anhydrous solvent , and there are many side ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D239/62
CPCC07D239/62
Inventor 刘金宝姚子健薛原
Owner SHANGHAI URBAN CONSTR VOCATIONAL COLLEGE
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