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Catalyst, system and method for catalytically preparing benzimidazolo[2,1-b]quinolin-6-one derivatives

A technology for benzimidazole and catalytic preparation, which is applied in the directions of organic compound/hydride/coordination complex catalysts, physical/chemical process catalysts, chemical instruments and methods, etc. Biodegradation and other problems, to achieve the effect of good recycling performance, high catalytic activity, and inhibition of side reactions

Active Publication Date: 2019-08-27
东营睿港投资服务有限责任公司
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0006] The purpose of the present invention is to overcome the disadvantages of the existing preparation process of benzimidazolo[2,1-b]quinolin-6-one derivatives, such as large amount of catalyst used, difficult biodegradation, high preparation cost and relatively complex preparation process. , providing a catalyst, system and method for catalytically preparing benzimidazolo[2,1-b]quinolin-6-one derivatives

Method used

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  • Catalyst, system and method for catalytically preparing benzimidazolo[2,1-b]quinolin-6-one derivatives
  • Catalyst, system and method for catalytically preparing benzimidazolo[2,1-b]quinolin-6-one derivatives
  • Catalyst, system and method for catalytically preparing benzimidazolo[2,1-b]quinolin-6-one derivatives

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preparation example Construction

[0040] The specific process of the preparation method of the present invention is as follows: the reaction raw materials and the catalyst are respectively added into the reaction vessel, mixed evenly with the reaction solvent, then placed in the microwave reactor for microwave heating reaction, and the power of the microwave reactor is controlled to be 300-350W, The reaction time is 8-14 minutes. After the reaction is completed, cool to room temperature, stand still, and filter with suction. The filter residue is washed with ethanol and vacuum-dried at 50°C to obtain benzimidazolo[2,1-b]quinolin-6-one Derivatives, and the filtrate obtained by the above-mentioned suction filtration can be reused without treatment.

[0041] The present invention is mainly aimed at the use of functionalized ionic liquids in the prior art to catalyze the preparation of benzimidazolo[2,1-b]quinolin-6-one derivatives in the process of using a large amount of catalyst, not easy to biodegrade, and the ...

Embodiment 1

[0046] 1mmol benzaldehyde, 1mmol 1,3-cyclohexanedione, 1mmol 2-aminobenzimidazole and 0.24mmol functionalized ionic liquid catalyst were respectively added to a belt containing 7ml 85% N,N-dimethylformamide aqueous solution In a 50ml single-necked flask with a condenser tube, fully shake the flask to fully mix the reaction system, place the flask in a microwave reactor, set the power of the reactor to 320W for the reaction, follow the reaction by TLC, and the reaction is completed in 14 minutes. After cooling to room temperature, a large amount of solids precipitated, crushed the solids, stood still, and filtered with suction. The resulting filter residue was washed with absolute ethanol (3ml×3), dried in vacuo to obtain benzimidazolo[2,1-b]quinoline-6 - Ketone, yield 84%. The filtrate was directly added with benzaldehyde, 1,3-cyclohexanedione and 2-aminobenzimidazole for repeated use.

[0047] The performance parameters of benzimidazolo[2,1-b]quinolin-6-one obtained in this ...

Embodiment 2

[0049] 1mmol p-fluorobenzaldehyde, 1mmol 1,3-cyclohexanedione, 1mmol 2-aminobenzimidazole and 0.16mmol functionalized ionic liquid catalyst were added to 8ml 85% N, N-dimethylformamide aqueous solution In a 50ml single-necked flask with a condenser tube, shake the flask fully to mix the reaction system fully, place the flask in a microwave reactor, set the power of the reactor to 320W for the reaction, follow the reaction by TLC, and the reaction ends in 12 minutes. After cooling to room temperature, a large amount of solids precipitated, crushed the solids, stood still, and filtered with suction. The obtained filter residue was washed with absolute ethanol (3ml×3), and dried in vacuo to obtain 5-(4-fluorophenyl)benzimidazolo[2 , 1-b] Quinolin-6-one in 87% yield. The filtrate was directly added with p-fluorobenzaldehyde, 1,3-cyclohexanedione and 2-aminobenzimidazole for repeated use.

[0050] The performance parameters of 5-(4-fluorophenyl)benzimidazo[2,1-b]quinolin-6-one obt...

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Abstract

The invention discloses a catalyst, a system and a method for achieving simple and convenient catalytic preparation of a benzimidazo [2, 1-b] quinolin-6-one derivative, and belongs to the technical field of preparation of chemical materials. The system comprises a reaction container, a microwave reactor, a suction filtration device, a washing device and a drying device. Aromatic aldehyde, 1, 3-cyclohexanedione and 2-aminobenzimidazole are used as reactive raw materials, and through selection of specific functionalized ionic liquid as a catalyst and in a microwave-assisted heating reaction way, the utilization rate of the raw materials and the yield rate of the obtained product can be effectively increased; the catalyst is relatively small in using amount, good in recycling performance and low in preparation cost and is conveniently produced industrially on a large scale.

Description

technical field [0001] The invention belongs to the technical field of chemical material preparation, and more specifically relates to a catalyst, system and method for catalytically preparing benzimidazolo[2,1-b]quinolin-6-one derivatives. Background technique [0002] Benzimidazole derivatives are a class of substances containing nitrogen heterocycles in their molecules, which can form hydrogen bonds with receptors in organisms, coordinate with metal ions, and have a wide range of biological activities, such as anticancer, antifungal, anti-inflammatory, therapeutic Hypoglycemia and physiological disorders, etc., are of great significance in medicinal chemistry. In recent years, the research on the synthesis and application of benzimidazole derivatives has never stopped and is still very active. In addition, heterocyclic compounds containing quinolinone structures also have a series of good physiological and biological activities, and have good applications in medical care...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D487/04B01J31/04
Inventor 沈智培卢华沈建忠
Owner 东营睿港投资服务有限责任公司
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