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3-substituted oxindole derivatives, and synthetic method and application thereof

A technology of indole derivatives and synthesis methods, applied in the field of 3-substituted oxindole derivatives and their chemical synthesis, achieving the effects of mild reaction conditions, high yield, and great application prospects

Inactive Publication Date: 2015-03-11
EAST CHINA NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0002] Oxindole compounds widely exist in natural compounds and drug molecules. Due to their special physiological activities, the synthesis of these compounds is one of the important fields of organic chemistry research, especially the asymmetric synthesis is more challenging.

Method used

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  • 3-substituted oxindole derivatives, and synthetic method and application thereof
  • 3-substituted oxindole derivatives, and synthetic method and application thereof
  • 3-substituted oxindole derivatives, and synthetic method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0059]

[0060] Aniline (0.1mmol), glyoxylate (0.11mmol), Molecular sieves (100 mg), H-BINOL phosphoric acid (0.01 mmol) and allyl palladium dichloride (0.005 mmol) were dissolved in 1 mL of dichloromethane to form a reaction system, and methyl-N-methyldiazoacetanilide (0.2 mmol) was dissolved in 1 mL of dichloromethane to form a solution. At 20° C., the solution of diazo compounds dissolved in dichloromethane was added dropwise to the reaction system within 1 hour using an auto-sampling pump. After the injection was completed, the reaction was continued to stir at 20° C. for 1 hour. The solvent was removed by rotary evaporation under reduced pressure to obtain a crude product, the structure of which was shown in formula (1-1). Purify the crude product by column chromatography (petroleum ether: ethyl acetate = 15:1-10:1) to obtain a pair of pure diastereoisomers. Total yield: 85%, dr value: 55:45 .

[0061] 1 H NMR (400MHz, CDCl 3 )δ7.35-7.30 (m, 2H), 7.18-7.06 (m, 3H...

Embodiment 2

[0064]

[0065] P-bromoaniline (0.1mmol), glyoxylate (0.11mmol), Molecular sieves (100 mg), H-BINOL phosphoric acid (0.01 mmol) and allyl palladium dichloride (0.005 mmol) were dissolved in 1 mL of dichloromethane to form a reaction system, and methyl-N-methyldiazoacetanilide (0.2 mmol) was dissolved in 1 mL of dichloromethane to form a solution. At 20° C., the solution of diazo compounds dissolved in dichloromethane was added dropwise to the reaction system within 1 hour using an auto-sampling pump. After the injection was completed, the reaction was continued to stir at 20° C. for 1 hour. The solvent was removed by rotary evaporation under reduced pressure to obtain a crude product, the structure of which was shown in formula (1-2). Purify the crude product by column chromatography (petroleum ether: ethyl acetate = 15:1-10:1) to obtain a pair of pure diastereomers respectively. Total yield: 80%, dr value: 60:40 .

[0066] 1 H NMR (400MHz, CDCl 3 )δ7.36-7.29 (m, 2H),...

Embodiment 3

[0069]

[0070] p-Chloroaniline (0.1mmol), glyoxylate (0.11mmol), Molecular sieves (100 mg), H-BINOL phosphoric acid (0.01 mmol) and allyl palladium dichloride (0.005 mmol) were dissolved in 1 mL of dichloromethane to form a reaction system, and methyl-N-methyldiazoacetanilide (0.2 mmol) was dissolved in 1 mL of dichloromethane to form a solution. At 20° C., the solution of diazo compounds dissolved in dichloromethane was added dropwise to the reaction system within 1 hour using an auto-sampling pump. After the injection was completed, the reaction was continued to stir at 20° C. for 1 hour. The solvent was removed by rotary evaporation under reduced pressure to obtain a crude product, the structure of which was shown in formula (1-3). Purify the crude product by column chromatography (petroleum ether: ethyl acetate = 15:1-10:1) to obtain a pair of pure diastereoisomers. Total yield: 82%, dr value: 60:40 .

[0071] 1 H NMR (400MHz, CDCl 3 )δ7.36-7.29(m, 2H), 7.13-7.07...

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Abstract

The invention relates to a kind of 3-substituted oxindole derivatives, and a synthetic method and application thereof. The synthetic method comprises: taking a diazo compound, an aryl amine and a glyoxylate as raw materiasl, taking a 4A molecular sieve as a water adsorber, taking BINOL phosphoric acid and allylpalladium chloride as a co-catalyst, taking an organic solvent as a solvent, and performing one-step reaction, so as to obtain the product. The method has the advantages of high atomic economy, high yield, mild reaction conditions, simple and safe operation, and the like. The 3-substituted oxindole derivatives each with two chiral centers can be taken as important chemical engineering and medicinal intermediates, and have wide application prospect in the field of pharmaceutical chemical engineering.

Description

technical field [0001] The invention relates to the field of synthetic medicine and chemical industry, and mainly relates to a 3-substituted oxindole derivative and its chemical synthesis method and application. Background technique [0002] Oxindole compounds widely exist in natural compounds and drug molecules. Due to their special physiological activities, the synthesis of these compounds is one of the important fields of organic chemistry research, especially the asymmetric synthesis is more challenging. [0003] Existing bibliography reports have the method for multiple synthesis oxindole, mainly focus on the asymmetric addition reaction (Chem.Sci., 2011,2,2035 to prochiral indole; Chen, Chem.Comm., 2009, 11, 3955; Org. Lett., 2009, 11, 3874). Among them, there are relatively few reports on the Mannich reaction. In 2012, Professor Hu Wenhao disclosed a high-efficiency synthesis method for 3-substituted oxindole derivatives using bisaryl imines, see Nature Chemistry 4,...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D209/34A61P35/00
CPCC07D209/34
Inventor 胡文浩黄海峰车久威邢栋
Owner EAST CHINA NORMAL UNIV
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