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Polychloromethyl-substituted indoline compound and synthetic method and application thereof

A technology of polychloromethyl group and synthetic method, applied in the directions of organic chemistry method, organic chemistry, drug combination, etc., can solve the problems such as unreported research work, and achieve the effects of simple post-processing, convenient processing, and wide application range of substrates.

Active Publication Date: 2018-12-07
JIANGSU UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

So far, no research work has been reported on the dichloromethylation or trichloromethylation of the indoline skeleton.

Method used

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  • Polychloromethyl-substituted indoline compound and synthetic method and application thereof
  • Polychloromethyl-substituted indoline compound and synthetic method and application thereof
  • Polychloromethyl-substituted indoline compound and synthetic method and application thereof

Examples

Experimental program
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Effect test

Embodiment 1

[0019] Under nitrogen protection, N-(2-methylallyl)-acetanilide 1a (0.2 mmol), di-tert-butyl peroxide (DTBP, 0.6 mmol), dichloromethane (2 mL) were added to a Schlenk reaction tube In, sealed. Heating to 100°C, the reaction time was 12 hours. After the reaction, the solvent was removed under reduced pressure, and the target product 3a was obtained by column chromatography with a yield of 78%.

Embodiment 2

[0021] Under nitrogen protection, N-(2-methylallyl)-acetyl-p-methylaniline 1b (0.2mmol), tert-butyl hydroperoxide (TBHP, 0.4mmol), dichloromethane (2mL) were added to Schlenk reaction tubes, sealed. Heating to 100°C, the reaction time was 24 hours. After the reaction, the solvent was removed under reduced pressure, and the target product 3b was obtained by column chromatography with a yield of 80%.

Embodiment 3

[0023] Under nitrogen protection, N-(2-methylallyl)-acetyl-p-ethoxyaniline 1c (0.2mmol), tert-butyl benzoyl peroxide (TBPB, 0.5mmol), dichloromethane (2mL ) into the Schlenk reaction tube and sealed. Heating to 120°C, the reaction time was 16 hours. After the reaction, the solvent was removed under reduced pressure, and the target product 3c was obtained by column chromatography with a yield of 76%.

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Abstract

The invention relates to a polychloromethyl-substituted indoline compound and a synthetic method and an application thereof, and specifically relates to the synthetic method of a 3-dichloromethyl and3-trichloromethyl-substituted indoline compound, which relates to the field of medicines, organic chemicals and fine chemicals. According to the method, N-(2-methylallyl)-acylarylamine compounds are utilized as raw materials, dichloromethane and carbon tetrachloride are utilized as sources of dichloromethyl and trichloromethyl, and a 3-dichloromethyl or 3-trichloromethyl-substituted N-acyl indoline compound is synthesized under catalysis of peroxide. Specific reaction conditions are that: tert-butyl hydroperoxide, tert-butyl peroxybenzoate, lauric aldehyde peroxide, di-tert-butyl peroxide, andbenzoyl peroxide are utilized as catalysts and free radical initiators under heating and stirring conditions. A reaction does not require participation of transition metal, an addition cyclization process of a free radical process is undergone, and post-treatment is simple, which is an effective way to synthesize the 3-dichloromethyl or 3-trichloromethyl-substituted N-acyl indoline compound.

Description

technical field [0001] The present invention relates to the fields of medicine, organic chemical industry and fine chemical industry, in particular to a polychloromethyl-substituted indoline compound and its synthesis method and application, specifically, the 3-position contains polychloromethyl substitution (dichloromethyl or The synthetic method of the indoline compound of trichloromethyl). Background technique [0002] Indoline (Indoline), also known as 2,3-dihydroindole, the skeleton structure widely exists in natural products and drug molecules with biological activity, in anti-tumor, anti-cancer, anti-inflammatory, anti-microbial and anti-malignant Areas such as Plasmodium play an extremely important role. It is also an important intermediate in organic synthesis reactions and has a wide range of applications in the field of materials science. However, compared with indole and indolone with similar structures, the construction of indoline is more difficult, the synth...

Claims

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Application Information

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IPC IPC(8): C07D209/10A61P35/00A61P29/00A61P31/00A61P33/06
CPCA61P29/00A61P31/00A61P33/06A61P35/00C07B2200/07C07D209/10Y02P20/55
Inventor 潘长多王赟高度杨震坤
Owner JIANGSU UNIV OF TECH
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