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Method for preparing pyridinoquinazolinone compound through catalysis of copper compound

A technology of pyridoquinazolone and copper compound, which is applied in the field of organic synthesis and metal catalysis, can solve the problems of unavailable and expensive, and achieve the effects of high yield, simple reaction operation, and the development of industrial production

Active Publication Date: 2018-02-16
GUANGZHOU UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0013] In the prior art, the reaction for synthesizing pyridoquinazolinone compounds is generally at a higher temperature, and most of the reaction raw materials are ortho-halogenated compounds, which are expensive and difficult to obtain.
Therefore, they are subject to certain restrictions in industrial production

Method used

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  • Method for preparing pyridinoquinazolinone compound through catalysis of copper compound
  • Method for preparing pyridinoquinazolinone compound through catalysis of copper compound
  • Method for preparing pyridinoquinazolinone compound through catalysis of copper compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0051] Example 1: 11H-pyrido[2,1-b]quinazolin-11-one

[0052] 248mg (1mmol) N- (quinolin-8-yl) benzamide and 188mg (2mmol) 2-aminopyridine, 18mg (0.1mmol) catalyst Cu (OAc) 2 ,540mg (2mmol) Oxidant K 2 S 2 o 8 , 3mL solvent dimethyl sulfoxide (DMSO) was added to a 30mL sealed tube under air. Then the sealed tube was placed in an oil bath at 100°C for 4 h. After the reaction was finished, the reaction solution was cooled to room temperature, 80 mL of ethyl acetate was added, and the column chromatography (ethyl acetate was used as eluent) combined the organic layers, and the organic layers were washed with water, dried over anhydrous sodium sulfate, filtered, and the filtrate was reduced to After pressure distillation, it was separated by silica gel column chromatography (ethyl acetate: petroleum ether = 1:3 as eluent) to obtain 163 mg of yellow solid with a yield of 83%.

[0053] The various characterization data of the resulting product are as follows:

[0054] M.p.=208...

Embodiment 2

[0067] Example 2: 3-Methyl-11H-pyrido[2,1-b]quinazolin-11-one

[0068] With 262mg (1mmol) 4-methyl-N-(quinolin-8-yl) benzamide and 188mg (2mmol) 2-aminopyridine, 18mg (0.1mmol) catalyst Cu(OAc) 2 ,540mg (2mmol) Oxidant K 2 S 2 o 8 , 3mL solvent dimethyl sulfoxide (DMSO) was added to a 30mL sealed tube under air. Then the sealed tube was placed in an oil bath at 100°C for 4 h. After the reaction was finished, the reaction solution was cooled to room temperature, 80 mL of ethyl acetate was added, and the column chromatography (ethyl acetate was used as eluent) combined the organic layers, and the organic layers were washed with water, dried over anhydrous sodium sulfate, filtered, and the filtrate was reduced to After pressure distillation, it was separated by silica gel column chromatography (ethyl acetate / petroleum ether: 1 / 3 as eluent) to obtain 168 mg of yellow solid with a yield of 80%.

[0069] The various characterization data of the resulting product are as follows:...

Embodiment 3

[0082] Example 3: 3-methoxy-11H-pyrido[2,1-b]quinazolin-11-one

[0083] With 278mg (1mmol) 4-methoxy-N-(quinolin-8-yl) benzamide and 188mg (2mmol) 2-aminopyridine, 18mg (0.1mmol) catalyst Cu(OAc) 2 ,540mg (2mmol) Oxidant K 2 S 2 o 8 , 3mL solvent dimethyl sulfoxide (DMSO) was added to a 30mL sealed tube under air. Then the sealed tube was placed in an oil bath at 100°C for 4 h. After the reaction was finished, the reaction solution was cooled to room temperature, 80ml of ethyl acetate was added, flash column chromatography (ethyl acetate was used as eluent), the organic layers were combined, the organic layer was washed with water, dried over anhydrous sodium sulfate, filtered, and the filtrate was reduced After pressure distillation, it was separated by silica gel column chromatography (ethyl acetate / petroleum ether: 1 / 3 as eluent) to obtain 190 mg of a yellow solid with a yield of 84%.

[0084] The various characterization data of the resulting product are as follows: ...

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Abstract

The invention belongs to the fields of organic synthesis and metal catalysis, and discloses a method for preparing a pyridinoquinazolinone compound through the catalysis of a copper compound. The method comprises the following steps: adding a benzamide derivative, a 2-aminopyridine derivative, a catalyst, an oxidizing agent and a solvent into a closed pipe in an air environment; then performing aheating reaction; and after the reaction is completed, purifying the obtained reaction solution to obtain the required pyridinoquinazolinone compound. According to the method, a C-H activation cascadereaction is performed on the benzamide derivative and the 2-aminopyridine derivative under the catalytic action of the copper compound in the presence of the oxidizing agent in the air environment and the closed environment, thereby generating the pyridinoquinazolinone; the method can be performed in the air environment; and the used raw materials, catalyst and oxidizing agent are simple and accessible, the reaction is simple to operate, and the yield is high, thereby being beneficial to industrial production.

Description

technical field [0001] The invention belongs to the fields of organic synthesis and metal catalysis, and in particular relates to a method for preparing pyridoquinazolone compounds by catalyzing copper compounds. Background technique [0002] 11H-pyrido[2,1-b]quinazolin-11-ones are a class of alkaloids containing nitrogen atoms. This kind of alkaloid substances has potent anti-inflammatory, anti-allergic, anti-convulsant, anti-cancer, sedative hypnotic, hypotensive and other biological activities, and has a wide range of uses in the field of medicine, which has aroused great interest of biomedical researchers. Therefore, it is of great practical value to develop a synthetic method for 11H-pyrido[2,1-b]quinazolin-11-one. [0003] Thomas Kappe etc. (Chemische Berichte, 1979,112 (10), 3424-3431) have reported that anthranilic acid and 2-bromopyridine obtain pyridoquinazolone under the action of copper powder and potassium carbonate, and the reaction formula is as follows 1. ...

Claims

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Application Information

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IPC IPC(8): C07D471/04
CPCC07D471/04
Inventor 刘吉旦邹金辉陈国术郑李垚刘运林
Owner GUANGZHOU UNIVERSITY
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