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Simple synthesizing method of uracil derivatives

A technology of derivatives and uracil, which is applied in the field of rapid preparation of uracil derivatives, can solve the problems of high activity requirements and limited application range of β-dicarbonyl compounds, and achieve short synthesis time, simple operation process, and easy synthesis The effect of short routes

Inactive Publication Date: 2017-09-08
CHONGQING UNIV OF ARTS & SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0003] At present, uracil compounds are prepared by condensation reaction of β-dicarbonyl compounds or their analogs with urea or thiourea in industry, but if urea is used as raw material, the activity requirements of β-dicarbonyl compounds are relatively high, which limits The scope of application of the reaction
At present, there are few reports on the synthesis of uracil compounds through multi-component reactions, and there is an urgent need for the attention and research of organic synthesis workers

Method used

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  • Simple synthesizing method of uracil derivatives
  • Simple synthesizing method of uracil derivatives
  • Simple synthesizing method of uracil derivatives

Examples

Experimental program
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Effect test

Embodiment 1

[0040] where R 1 is aryl, R 2 is an alkyl group, that is, 2-benzyl-4-(p-tolyl)pyrimido[1,6- a ] indole-1,3,5 (2 H )-triketone synthesis, the specific steps are as follows:

[0041] In a 10 mL microwave reaction tube, first dissolve ethyl glyoxylate (1.5 mmol) and methyl 2-aminobenzoate (1.0 mmol) in 2.0 mL of methanol solution, and then add p-methyl Benzoylformic acid (1.0 mmol) and benzyl isocyanide (1.0 mmol) were sequentially added to the solution, the reaction solution was stirred overnight at room temperature, and then the isocyanate was detected by TLC, if there was no remaining isocyanine starting material , the solution was blown dry with nitrogen, then dissolved in 5.0 ml of dimethylformamide (DMF), and then added 1,8-diazabicycloundec-7-ene (DBU) (2.0 mmol), 100 in the microwave o C for 10 minutes. The solution was diluted with ethyl acetate (15 ml), and washed three times with 20 ml of saturated brine. After the organic phase was dried with magnesium sulfate,...

Embodiment 2

[0044] where R 1 is aryl, R 2 is an alkyl group, that is, 2-phenethyl-4-phenylpyrimido[1,6- a ] indole-1,3,5 (2 H )-triketone synthesis, the specific steps are as follows:

[0045] In a 10 mL microwave reaction tube, first dissolve ethyl glyoxylate (1.5 mmol) and methyl 2-aminobenzoate (1.0 mmol) in 2.0 mL of methanol solution, and then dissolve benzoyl Formic acid (1.0 mmol) and phenethyl isocyanide (1.0 mmol) were added to the solution in turn, and the reaction solution was stirred overnight at room temperature, and then the isocyanate was detected by thin-layer chromatography. If there was no remaining isocyanine raw material, the solution Blow dry with nitrogen, then dissolve with 5.0 ml of dimethylformamide (DMF), then add 1,8-diazabicycloundec-7-ene (DBU) (2.0 mmol), in the microwave Medium 100 o C for 10 minutes. The solution was diluted with ethyl acetate (15 ml), and washed three times with 20 ml of saturated brine. After the organic phase was dried with magnes...

Embodiment 3

[0048] where R 1 is aryl, R 2 is an alkyl group, that is, 2-benzyl-4-(p-tolyl)pyrimido[1,6- a ] indole-1,3,5 (2 H )-triketone synthesis, the specific steps are as follows:

[0049] In a 10 mL microwave reaction tube, first dissolve ethyl glyoxylate (1.5 mmol) and methyl 2-aminobenzoate (1.0 mmol) in 2.0 mL of methanol solution, and then add p-bromobenzene Formylformic acid (1.0 mmol) and benzyl isocyanide (1.0 mmol) were sequentially added to the solution, and the reaction solution was stirred overnight at room temperature, and then the isocyanate was detected by thin-layer chromatography. If there was no remaining isocyanate, The solution was blown dry with nitrogen, then dissolved in 5.0 ml of dimethylformamide (DMF), and then added 1,8-diazabicycloundec-7-ene (DBU) (2.0 mmol), in 100 in the microwave o C for 10 minutes. The solution was diluted with ethyl acetate (15 ml), and washed three times with 20 ml of saturated brine. After the organic phase was dried with mag...

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Abstract

The invention relates to a preparation method and application of uracil derivatives. On the basis of a Ugi reaction, carboxylic acid, methyl-2-aminobenzoate, ethyl glyoxalate and isocyanide are used as raw materials, and the uracil derivatives are synthesized in a one-pot mode under the alkaline condition with the assistance of microwaves. The synthesizing method has the advantages of being simple in operation, short in synthesizing route, low in cost and the like, and is suitable for quick synthesis of the uracil derivatives.

Description

technical field [0001] This application relates to the field of drug synthesis, especially a rapid preparation method of uracil derivatives. Background technique [0002] Uracil is a base unique to RNA and is equivalent to thymine (T) in DNA. It is one of the four bases that make up RNA. Uracil is the stable ketone structure of 2,4-dihydroxypyrimidine. It is an important intermediate in the synthesis of antineoplastic drug 5-fluorouracil and its derivative drugs such as tegafur, bisfurfururacil, doxifluridine, carmofur and antiviral 5-iodo 2'-deoxyuridine. Since C. Heidelberger et al first synthesized 5-fluorouracil in 1957 and discovered its good physiological activity (Nature, 1957,179,633), chemists and pharmacologists have done a lot of research on it. So far, 5-fluorouracil has been widely used in the clinical treatment of various tumors, such as the treatment of digestive system cancer, head and neck cancer, gynecological cancer, liver cancer, bladder cancer, pancre...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D487/04A61P35/00
CPCC07D487/04
Inventor 徐志刚陈中祝
Owner CHONGQING UNIV OF ARTS & SCI
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