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Substituted furan isoquinolinone derivatives and preparation method thereof

A technology of furan isoquinolinone and derivatives, which is applied in the field of medicinal chemistry, can solve the problems of many by-products, difficult purification, harsh reaction conditions, etc., and achieve the effect of simple steps

Active Publication Date: 2018-09-18
ZHEJIANG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] The synthesis of isoquinoline rings has always been paid special attention by organic synthetic chemists and pharmaceutical synthetic chemists. Although there have been many reports on the synthesis of isoquinoline derivatives in recent years, they are not satisfactory because their reaction conditions are often It is relatively harsh, but the yield is not high, and there are many by-products, the purification is difficult, and some methods must use expensive catalysts, so it is urgent to develop new methods for the synthesis of isoquinoline and its derivatives that are simple and effective.

Method used

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  • Substituted furan isoquinolinone derivatives and preparation method thereof
  • Substituted furan isoquinolinone derivatives and preparation method thereof
  • Substituted furan isoquinolinone derivatives and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0037] Disperse 1,3-cyclohexanedione and potassium hydroxide uniformly in water, stir at room temperature for 5 minutes, add ethyl chloroacetoacetate in methanol, then stir the system at room temperature for 5 days, and then use 4N Acidify with hydrochloric acid, filter the acidified reaction solution, and the solid obtained is the product: ethyl 3-methyl-4-oxo-4,5,6,7-tetrahydrobenzofuran-2-carboxylate. In this step, the molar ratio of 1,3-cyclohexanedione to potassium hydroxide and ethyl chloroacetoacetate is 1:1:1, and the amount of 1,3-cyclohexanedione corresponding to each milliliter of water is 0.1g , The feed amount of ethyl chloroacetoacetate per milliliter of methanol is 0.2g. The yield of this step is 65%. The structure of the resulting product is:

[0038]

[0039] Molecular formula: C 12 H 14 O 4

[0040] Chinese name: ethyl 3-methyl-4-oxo-4,5,6,7-tetrahydrobenzofuran-2-carboxylate

[0041] English name: ethyl 3-methyl-4-oxo-4,5,6,7-tetrahydrobenzofuran-2-carboxylate ...

Embodiment 2

[0046] Dissolve ethyl 3-methyl-4-oxo-4,5,6,7-tetrahydrobenzofuran-2-carboxylate and potassium hydroxide in a mixed solvent of methanol and water, and stir the system at room temperature after dissolution Reaction for 5h. Then adjust the pH of the reaction solution to 1 with 6N hydrochloric acid, filter the reaction solution, and the solid obtained by filtration is the product: 3-methyl-4-oxo-4,5,6,7-tetrahydrobenzofuran-2- Formic acid. The mixed solvent used in this step is a 2.5:1 formula of methanol and water. The feed amount of ethyl 3-methyl-4-oxo-4,5,6,7-tetrahydrobenzofuran-2-carboxylate per milliliter of mixed solvent is 0.2g. In this step, the molar ratio of ethyl 3-methyl-4-oxo-4,5,6,7-tetrahydrobenzofuran-2-carboxylate to potassium hydroxide is 1:6. The yield of this step is 90%. The structure of the resulting product is:

[0047]

[0048] Molecular formula: C 10 H 10 O 4

[0049] Chinese name: 3-methyl-4-oxo-4,5,6,7-tetrahydrobenzofuran-2-carboxylic acid

[0050] En...

Embodiment 3

[0056] Disperse 3-methyl-4-oxo-4,5,6,7-tetrahydrobenzofuran-2-carboxylic acid uniformly in diethylene glycol, add copper powder and pyridine, and then heat the system to 175°C, Keep stirring for 10h. The system was cooled to room temperature, ice water was added, and acidified with 4N hydrochloric acid. The acidified reaction solution was extracted three times with petroleum ether. The combined extract was washed with water once, and then the extract was dried with anhydrous sodium sulfate and spin-dried. The resulting solid is the product: 3-methyl-6,7-dihydrobenzofuran-4-(5H)-one. In this step, the amount of 3-methyl-4-oxo-4,5,6,7-tetrahydrobenzofuran-2-carboxylic acid corresponding to each milliliter of diethylene glycol is 0.1 g. In this step, the molar ratio of 3-methyl-4-oxo-4,5,6,7-tetrahydrobenzofuran-2-carboxylic acid to copper powder and pyridine is 1:1:2. The yield of this step was 85%. The structure of the resulting product is:

[0057]

[0058] Molecular formula:...

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PUM

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Abstract

The invention relates to the field of medical chemistry, and aims at providing a substituted furan flavonol derivative and a preparation method thereof. The substituted furan flavonol derivative has a structure represented by formula (I) shown in the description; and in the formula (I), B ring is selected from a phenyl group or a furyl group; and R1, R2 and R3 are respectively independently selected from the hydrogen atom, a hydroxyl group, a methoxy group, a dimethylamino group, a nitro group and a cyan group. The above product is a new skeleton natural furan isoquinolone analog and has potential drug activity, and the preparation method of the compound provides support for the drug activity researches of furan isoquinolones. The preparation method of the derivative has the advantages of simple steps and easiness in obtaining, and is of great significance to industrial production.

Description

Technical field [0001] The present invention relates to the field of medicinal chemistry, and more specifically, to a substituted furan isoquinolinone derivative and a preparation method thereof. Background technique [0002] Isoquinolinone compounds widely exist in nature, and their derivatives have a variety of biological activities such as vasodilation and anti-tumor. The molecular diversity, synthesis methods and biological activities of isoquinolinone compounds have received attention in recent years. [0003] The synthesis of isoquinoline rings has always been paid special attention by synthetic organic chemists and pharmaceutical synthetic chemists. Although there have been many reports of synthetic isoquinoline derivatives in recent years, they are not satisfactory because their reaction conditions are often It is relatively harsh, but the yield is not high, and the by-products are many, and purification is difficult. Some methods must use expensive catalysts. Therefore, it...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D498/04
CPCC07D498/04
Inventor 吴军何兴瑞娄永根商志才顾海宁
Owner ZHEJIANG UNIV
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