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Benzo[f]pyridin[1,2-a]indole-6,11-dione derivative and preparation method thereof

A 2-a, derivative technology, applied in the direction of organic chemistry, can solve the problems of limited synthetic product types, naphthoquinone types, poor atom economy and step economy, and achieve improved atom economy and step economy, Conducive to the protection of the environment, the effect of excellent biological activity

Active Publication Date: 2019-04-30
XUZHOU NORMAL UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0005] The disadvantage of this method is that 2,3-dichloronaphthoquinones are relatively expensive, and substituted 2,3-dichloronaphthoquinones are difficult to obtain, which greatly limits the types of synthetic products
[0008] The disadvantage of this method is that 2-substituted naphthoquinones are difficult to obtain, and they need to be synthesized by themselves when used, and the types of synthesized 2-substituted naphthoquinones are greatly limited
Compared with the direct use of acetophenone as a raw material, the reaction cost of this method is relatively expensive, and the atom economy and step economy are poor

Method used

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  • Benzo[f]pyridin[1,2-a]indole-6,11-dione derivative and preparation method thereof
  • Benzo[f]pyridin[1,2-a]indole-6,11-dione derivative and preparation method thereof
  • Benzo[f]pyridin[1,2-a]indole-6,11-dione derivative and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0033] (1) 12-benzoylbenzo[f]pyrido[1,2-a]indole-6,11-dione (12-Benzoylbenzo[f]pyrido[1,2-a]indole-6,11 -dione) (compound 5a):

[0034] Add 10 mmol of 1,4-naphthoquinone, 30 mmol of pyridine, 10 mmol of acetophenone, 1 mmol of copper bromide, and 50 mL of acetonitrile into a 250 mL round bottom flask and set the reactor temperature to 85°C, the round bottom flask was heated to reflux in the reactor for 12 hours. After the reaction, the acetonitrile solvent was distilled off under reduced pressure, then 50 ml of water was added, and then extracted three times with 20 ml of chloroform, the extracts were combined, washed with water, and dried over anhydrous sodium sulfate. Finally, the chloroform was distilled off under reduced pressure, and the obtained solid was recrystallized using absolute ethanol to obtain a red solid product, the melting point of which was measured to be 256-257.5°C.

[0035] (2) Characterization of the product

[0036] Structural characterization of the...

Embodiment 2

[0048] (1) 12-(4-methylbenzoyl)benzo[f]pyridin[1,2-a]indole-6,11-dione (12-(4-methylbenzoyl)benzo[f]pyrido[ 1,2-a] indole-6,11-dione) (compound 5b) preparation:

[0049] Add 10 mmol of 1,4-naphthoquinone, 20 mmol of pyridine, 10 mmol of p-methylacetophenone, 1.5 mmol of copper bromide, and 50 mL of acetonitrile into a 250-mL round-bottomed flask, set The temperature of the reactor was 80 degrees, and the round bottom flask was heated to reflux in the reactor for 10 hours. After the reaction, the acetonitrile solvent was distilled off under reduced pressure, then 50 ml of water was added, and then extracted three times with 20 ml of chloroform, the extracts were combined, washed with water, and dried over anhydrous sodium sulfate. Finally, the chloroform was distilled off under reduced pressure, and the obtained solid was recrystallized using absolute ethanol to obtain a red solid product. The red solid product was found to have a melting point of 217-220°C.

[0050] (2) Cha...

Embodiment 3

[0061] (1) 12-(4-isopropylbenzoyl)benzo[f]pyridin[1,2-a]indole-6,11-dione (12-(4-isopropylbenzoyl)benzo[f]pyrido Preparation of [1,2-a]indole-6,11-dione) (compound 5c):

[0062] Add 10 millimoles of 1,4-naphthoquinone, 25 millimoles of pyridine, 10 millimoles of p-isopropylacetophenone, 1.5 millimoles of copper bromide and 50 milliliters of acetonitrile into a 250-ml round-bottomed flask, The reactor temperature was set at 85 degrees, and the round bottom flask was heated to reflux in the reactor for 6 hours. After the reaction, the acetonitrile solvent was distilled off under reduced pressure, then 50 ml of water was added, and then extracted three times with 20 ml of chloroform, the extracts were combined, washed with water, and dried over anhydrous sodium sulfate. Finally, the chloroform was distilled off under reduced pressure, and the obtained solid was recrystallized using absolute ethanol to obtain a red solid product. The red solid product was found to have a melting...

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Abstract

The invention provides a benzo[f]pyridine[1,2-a]indol-6,11-diketone derivative and a preparation method thereof. The preparation method is characterized by preparing the benzo[f]pyridine[1,2-a]indol-6,11-diketone derivative from 1,4-naphthoquinone or substituted 1,4-naphthoquinone, a pyridine compound and acetophenone or substituted acetophenone under the existence of copper bromide. According to the benzo[f]pyridine[1,2-a]indol-6,11-diketone derivative and the preparation method thereof, provided by the invention, the acetophenone or the substituted acetophenone is directly adopted as a substrate to react with the 1,4-naphthoquinone or substituted 1,4-naphthoquinone and the pyridine compound, and the step of acetophenone bromination is omitted, so that atom economy and the step economy of the reaction are greatly increased, and the environment is favorably protected; meanwhile, according to the preparation method, the varieties of substituent groups on a naphthoquinone ring in a product are greatly extended, synthesis of wider benzo[f]pyridine[1,2-a]indol-6,11-diketone derivatives becomes possible, and wider activity research on the compounds becomes possible.

Description

technical field [0001] The invention relates to the technical field of preparation of biologically active compounds, in particular to a benzo[f]pyridine[1,2-a]indole-6,11-dione derivative and a preparation method thereof. Background technique [0002] Benzo[f]pyridine[1,2-a]indole-6,11-dione derivatives are a class of compounds with excellent biological activity and are widely used in the field of biomedicine. Existing methods for synthesizing benzo[f]pyridin[1,2-a]indole-6,11-dione derivatives mainly include the following three types: [0003] Method one, with 2,3-dichloronaphthoquinone as substrate, 2,3-dichloronaphthoquinone is reacted with the amine salt that bromoacetophenone and substituted pyridine generate, and the chemical reaction formula of this method is as formula (1 ) shown. [0004] [0005] The disadvantage of this method is that 2,3-dichloronaphthoquinones are relatively expensive, and substituted 2,3-dichloronaphthoquinones are difficult to obtain, whi...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D487/04
CPCC07D487/04
Inventor 刘蕴吴翚韩军文王文慧
Owner XUZHOU NORMAL UNIVERSITY
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