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Pyridine-quinazolinone compound and preparation method thereof

A technology for pyridoquinazolones and compounds, applied in the field of pyridoquinazolone compounds and their preparation, capable of solving the problems of limited reaction raw materials, harsh reaction conditions, expensive reaction reagents, etc. The effect of wide range, high reaction yield and simple operation

Inactive Publication Date: 2013-06-26
SHANGHAI UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0026] In summary, there are many methods for preparing pyridoquinazolone compounds, but the raw materials for these reactions are not easy to obtain, and need to go through more complicated synthesis steps; the reaction raw materials in some reactions have relatively large limitations, and the reaction products The rate is low, the reaction reagents are expensive, and the reaction conditions are relatively harsh, etc.

Method used

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  • Pyridine-quinazolinone compound and preparation method thereof
  • Pyridine-quinazolinone compound and preparation method thereof
  • Pyridine-quinazolinone compound and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0042] Embodiment one: 11 H -pyrido[2,1- b ]quinazolin-11-one

[0043] 11 H -pyrido[2,1- b ] quinazoline-11-ketone adopts the following steps: 1. add 14.6 grams of 2-(2-bromophenyl)- N -(pyridin-2-yl)acetamide, 2.7 grams of 1,10-phenanthroline, 1.3 grams of cuprous iodide, 20 grams of potassium acetate, 20 grams of tetrabutylammonium chloride, 200 milliliters of DMF, heated to 90~ 100°C. Track the reaction with thin layer chromatography, to the reaction raw material 2-(2-bromophenyl)- N-(pyridin-2-yl)acetamide disappears; 2. after the reaction finishes, filter the system with diatomaceous earth and remove the solvent with a rotary evaporator to obtain a crude product; 3. use column chromatography for the crude product (petroleum ether: ethyl acetate = 5:1) Purification afforded 9.3 g of 11 H -pyrido[2,1- b ] quinazoline-11-one, the productive rate is 95%. Melting point: 208-210°C.

[0044] -1 1698, 1641, 1527, 1456, 764.

[0045] 1 H NMR (CDCl 3 , 500 M...

Embodiment 2

[0054] Example 2: 6-Methyl-11 H -pyrido[2,1- b ]quinazolin-11-one

[0055] 6-Methyl-11 H -pyrido[2,1- b ] quinazoline-11-ketone adopts the following steps: 1. add 15.3 grams of 2-(2-bromophenyl)- N -(3-methylpyridin-2-yl)acetamide, 2.9 g 1,10-phenanthroline, 1.6 g cuprous iodide, 15 g potassium acetate, 22 g tetrabutylammonium bromide, 200 ml DMF, Heat to 90-100°C. Track the reaction with thin layer chromatography, to the reaction raw material 2-(2-bromophenyl)- N -(3-methylpyridin-2-yl)acetamide disappears; 2. after the reaction finishes, filter the system with diatomaceous earth and remove the solvent with a rotary evaporator to obtain a crude product; 3. use column chromatography for the crude product (petroleum ether: Ethyl acetate = 5 : 1) purification to obtain 9.1 g of 6-methyl-11 H -pyrido[2,1- b ] Quinazoline-11-one, the productive rate is 87%. Melting point: 128-130°C.

[0056] -1 1699, 1641, 1530, 1456, 764.

[0057] 1 H NMR (CDCl 3 , 500 MH...

Embodiment 3

[0066] Example Three: 11-Oxygen-11 H -pyrido[2,1- b ]Quinazoline-6-carboxylic acid ethyl ester

[0067] 11-oxo-11 H -pyrido[2,1- b ] ethyl quinazoline-6-carboxylate adopts the following steps: 1. add 18.2 grams of 2-(2-(2-bromophenyl) acetamido) ethyl nicotinate in 250 milliliters of round bottom flasks, 2.9 grams 1,10-Phenanthroline, 1.6 g of cuprous iodide, 15 g of potassium acetate, 22 g of tetrabutylammonium iodide, 200 ml of DMF, heated to 90-100 °C. Use thin layer chromatography to track the reaction until the reaction raw material 2-(2-(2-bromophenyl)acetamido)ethyl nicotinate disappears; ②After the reaction is over, filter the system with diatomaceous earth and use rotary evaporation The crude product was obtained by removing the solvent with an instrument; ③ the crude product was purified by column chromatography (petroleum ether: ethyl acetate = 5: 1) to obtain 7.4 g of 11-oxo-11 H -pyrido[2,1- b ] Quinazoline-6-carboxylic acid ethyl ester, productive rate is 5...

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Abstract

The invention relates to a pyridino-quinazolinone compound and a preparation method thereof. The structural formula of the compound is shown in the specification, wherein R1=-Ome or H; and R2=-H, -Me, -Ph, -CO2Et, or-Br. The substituted pyridino-quinazolinone compound disclosed by the invention is an important pharmaceutical molecular active skeleton and organically synthesized intermediate, and plays an important role in pharmaceutical chemistry. According to the method, raw materials are available, the reaction yield is high, and the applicable scope of a substrate is wide. Conventional solvents are used in reaction, the operation is simple, the conditions are mild, the reaction is environment-friendly, and the reaction yield is up to 95%, and therefore, the pyridine-quinazolinone compound and the preparation method thereof disclosed by the invention are extremely suitable for industrial production.

Description

technical field [0001] The invention relates to a pyridoquinazolinone compound and a preparation method thereof. Background technique [0002] Nitrogen-containing heterocycle is a very common pharmacophore in the field of drug research, and it is one of the important targets of small molecule drug development today. In recent years, most of the top-selling branded drugs in the world have nitrogen-containing heterocyclic skeletons. The antibacterial, anti-tumor and other physiological activities of nitrogen-containing heterocyclic compounds, as well as their significance in basic theory and applied research, make the synthesis of such compounds and the study of their chemical and biological properties an important topic in organic chemistry and related fields. Hot topic. while 11 H -pyrido[2,1- b ]Quinazolin-11-one is a class of nitrogen-containing heterocycles, which are widely used in the field of medicine. These compounds have shown excellent biological activities in ...

Claims

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Application Information

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IPC IPC(8): C07D487/04
Inventor 许斌孙杰刘秉新
Owner SHANGHAI UNIV
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