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A kind of synthetic method of 6h-isoindolo[2,1-α]indole-6-one derivative

A synthetic method, the technology of isoindole, applied in the direction of organic chemistry, etc., can solve the problems of low utilization rate of reaction atoms, lengthy reaction steps, expensive preparation cost, etc., and achieve the effect of simple operation, less by-products and wide application range

Inactive Publication Date: 2017-11-07
FUJIAN NORMAL UNIV
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

The above four paths have disadvantages: the raw materials do not exist widely in nature, they need to be prepared in advance, and the preparation cost is expensive; the reaction steps are lengthy, the operation steps are complicated, and there are many by-products; the utilization rate of reaction atoms is low

Method used

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  • A kind of synthetic method of 6h-isoindolo[2,1-α]indole-6-one derivative
  • A kind of synthetic method of 6h-isoindolo[2,1-α]indole-6-one derivative
  • A kind of synthetic method of 6h-isoindolo[2,1-α]indole-6-one derivative

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preparation example Construction

[0022] A method for synthesizing 6H-isoindolo[2,1-α]indol-6-one derivatives, comprising the following steps:

[0023] Add a magnetic stirrer, 2-(2-iodophenyl)-indole, catalyst, ligand, base, organic solvent into a 25ml vial, cover the vial, insert a needle, and put a small amount of silicone oil into a 50mL high-pressure Then put 20atm CO gas into the autoclave, and react in an oil bath at 90-110°C for 20-24 hours. After the reaction is completed, the product obtained is extracted with ethyl acetate as the extraction agent, and then washed with distilled water Three times, add anhydrous magnesium sulfate to dry, filter, and then concentrate the filtrate by rotary evaporation to obtain the crude product. The crude product uses petroleum ether and ethyl acetate as eluent, and uses 200-300 mesh silica gel as the separation resin for column chromatography. 6H-isoindolo[2,1-α]indol-6-one was isolated;

[0024] Wherein, the consumption of the catalyst is 5-10% of the molar consumpt...

Embodiment 1

[0031] 6H-isoindolo[2,1-α]indol-6-ketone (R in structural formula I 1 = H, R 2 =H) synthetic method, comprises the following steps:

[0032] To a 25ml vial was added 0.5mmol (159.6mg) 2-(2-iodophenyl)-1H-indole, 0.05mmol (11.2mg) Pd(OAc) 2 , 0.1mmol (26.2mg) PPh 3 , 0.5mL Et 3 N and 2mL N,N-dimethylformamide, cap the vial, insert a needle, put it into a 50mL autoclave filled with a small amount of silicone oil, put 20atm CO into the autoclave, and put it in an oil bath at 100°C React for 24 hours. After the reaction is over, the obtained product is extracted with ethyl acetate as an extractant, washed three times with distilled water, dried by adding anhydrous magnesium sulfate, filtered, and the filtrate is concentrated by rotary evaporation to obtain a crude product. The crude product is extracted with petroleum ether and acetic acid Ethyl ester mixture (volume ratio 30:1) is used as eluent column separation (200-300 mesh silica gel) to obtain 6H-isoindolo[2,1-α]indol-6-...

Embodiment 2

[0039]2-Methyl-6H-isoindolo[2,1-α]indol-6-one (R in structural formula I 1 =CH 3 , R 2 =H) synthetic method, comprises the following steps:

[0040] To a 25 ml vial was added 0.5 mmol (167.1 mg) 2-(2-iodophenyl)-5-methyl-1H-indole, 0.025 mmol (5.6 mg) Pd(OAc) 2 , 0.05mmol (13.1mg) PPh 3 , 0.5mmol (69.1mg) K 2 CO 3 , then add 1mL of toluene solvent, cap the vial, insert a needle, put it into a 50mL autoclave filled with a small amount of silicone oil, put 20atm CO into the autoclave, and react in an oil bath at 100°C for 24 hours, and the reaction is complete Finally, the resulting product was extracted with ethyl acetate as an extractant, washed three times with distilled water, dried by adding anhydrous magnesium sulfate, filtered, and then the filtrate was concentrated by rotary evaporation to obtain a crude product, which was prepared with petroleum ether and ethyl acetate The mixed solution (volume ratio 30:1) is used for eluent column separation (200-300 mesh silica...

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Abstract

The invention discloses a synthesis method of a 6H-isoindolo[2, 1-alpha]indol-6-one derivative. The synthesis method comprises the following steps: putting 2-(2-iodophenyl)-indol, a catalyst, a ligand and alkali into an organic solvent in an autoclave; filling the system with a CO gas with certain pressure for a carbonylation reaction; and after the reaction, performing column chromatographic separation to obtain the 6H-isoindolo[2, 1-alpha]indol-6-ketone derivative. According to the method disclosed by the invention, the 6H-isoindolo[2, 1-alpha]indol-6-one derivative is synthesized in one step by taking carbon monoxide as a carbon source, and the catalyst system is simple and easy to operate.

Description

technical field [0001] The invention belongs to the technical field of catalytic synthesis of fine chemical products, and in particular relates to a synthesis method of 6H-isoindolo[2,1-α]indol-6-one derivatives. Background technique [0002] Compounds with 6H-isoindolo[2,1-α]indol-6-one as the backbone are widely distributed in nature and are the active ingredients of many medicinal plants with rich biological activity and pharmaceutical value. Especially in the protection of nuclear DNA, preventing cell canceration, anti-cancer cell proliferation has outstanding performance. At present, the methods for preparing 6H-isoindolo[2,1-α]indol-6-one mainly include: (1) first carry out witting reaction by 2-nitrobenzaldehyde and phosphine ylide, and then carry out lactam ring reaction after reduction; (2) react tert-butyl isocyanide with 2-(2-bromophenyl)indole; (3) amidate 2-(2,2-bromovinyl)aniline with acyl halide The reaction is then prepared through a two-step de-HBr couplin...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D487/04
CPCC07D487/04
Inventor 黄秋锋傅淑蓉李彬彬张晓凤林深
Owner FUJIAN NORMAL UNIV