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A kind of C-3 fully substituted oxindole derivative and its synthesis method and application

A technology of indole derivatives and synthesis methods, which is applied in the field of synthetic medicine and chemical industry, and can solve the problems that are not conducive to the application of C-3 fully substituted oxindole derivatives and their industrial synthesis and industrialization. The post-processing is cumbersome and other problems, and the effect of low cost, few reaction steps and short reaction route is achieved

Inactive Publication Date: 2019-02-01
EAST CHINA NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Afterwards, new synthetic methods were discovered one after another, but these new synthetic methods and routes have disadvantages such as long steps, high cost, long time-consuming, low yield, cumbersome operation and post-processing, etc., and are difficult to be applied on a large scale in industrialization. limited economic value
Therefore, above-mentioned method is all unfavorable for containing the application of C-3 fully substituted oxindole derivatives in organic synthesis and its industrialization

Method used

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  • A kind of C-3 fully substituted oxindole derivative and its synthesis method and application
  • A kind of C-3 fully substituted oxindole derivative and its synthesis method and application
  • A kind of C-3 fully substituted oxindole derivative and its synthesis method and application

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Embodiment 1

[0093]

[0094] Dissolve MBH carbonate (0.2mmol), β-ICD (0.25mmol) and allylpalladium chloride (0.05mmol) in 1mL i-PrOAc:DCM=1:1 mixed solvent, and prepare mixed solution A, in Stir at room temperature for 10 minutes. Then N-alkyl-N-aryl diazoamide (0.3 mmol) was dissolved in 1 mL i-PrOAc:DCM = 1:1 mixed solvent to prepare solution B. solution B at 20 o C, add mixed solution A with a syringe pump within 1 hour. Stir for 36 to 48 hours, and the reaction mixture is purified by column chromatography to obtain a pure product whose structure is shown in formula (a), which is tert-butyl-2-((R)-(4-bromophenyl)-( R)-1,3-dimethyl-2-oxindole-3-substituted)meth)acrylate, the yield is 64%, the dr value is equal to 95:5, and the ee value is greater than 99%. Compound shown in formula (a) 1 H NMR schematic as figure 1 As shown, its 13 C NMR schematic as figure 2 As shown, the liquid phase diagram of the racemic product is shown in image 3 As shown, the liquid phase diagram of i...

Embodiment 2

[0097]

[0098]Dissolve MBH carbonate (0.2mmol), β-ICD (0.25mmol) and allylpalladium chloride (0.05mmol) in 1mL i-PrOAc:DCM=1:1 mixed solvent, and prepare mixed solution A, in Stir at room temperature for 10 minutes. Then N-alkyl-N-aryl diazoamide (0.3 mmol) was dissolved in 1 mL i-PrOAc:DCM = 1:1 mixed solvent to prepare solution B. Add solution B to mixed solution A with a syringe pump within 1 hour at 20°C. Stir for 36 to 48 hours, and the reaction mixture is purified by column chromatography to obtain a pure product whose structure is shown in formula (b), which is methyl-2-((R)-((R)-5-bromo-1 , 3-Dimethyl-2-oxindole-3-substituted) (phenyl) meth)acrylate, the yield was 75%, the dr value was equal to 91:9, and the ee value was race. Compound shown in formula (b) 1 H NMR schematic as Figure 5 As shown, its 13 C NMR schematic as Image 6 shown.

[0099] 1 H NMR (400MHz, CDCl 3 )δ7.31(m,6H),6.90(s,1H),6.30(s,1H),5.54(s,1H),4.63(s,1H),3.64(s,3H),3.09(s,3H ),1.38(s...

Embodiment 3

[0101]

[0102] Dissolve MBH carbonate (0.2mmol), β-ICD (0.25mmol) and allylpalladium chloride (0.05mmol) in 1mL i-PrOAc:DCM=1:1 mixed solvent, and prepare mixed solution A, in Stir at room temperature for 10 minutes. Then N-alkyl N-aryl diazoamide (0.3 mmol) was dissolved in 1 mL of i-PrOAc:DCM = 1:1 mixed solvent to prepare solution B. Add solution B to mixed solution A with a syringe pump within 1 hour at 20°C. Stirring for 36-48 hours, the reaction mixture was purified by column chromatography to obtain a pure product, the structure of which was shown in formula (c), which was tert-butyl-2-((R)-((R)-1,3- Dimethyl-2-oxindole-3-substituted)(phenyl)meth)acrylates with a yield of 64%, a dr value greater than 95:5, and an ee value equal to 84%. Compound shown in formula (c) 1 H NMR schematic as Figure 7 As shown, its 13 C NMR schematic as Figure 8 As shown, the liquid phase diagram of the racemic product is shown in Figure 9 As shown, the liquid phase diagram of it...

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Abstract

The invention discloses a C-3-containing fully-substituted oxindole derivative and a synthesizing method thereof. The C-3-containing fully-substituted oxindole derivative is obtained by taking a diazo compound and MBH carbonate as raw materials and taking chiral organic alkali and allyl palladium chloride as co-catalyst through a one-step reaction in an organic solvent. The synthesizing method has the advantages of being high in atom economy and selectivity, the reaction conditions are mild, and operation is easy and safe. The C-3-containing fully-substituted oxindole derivative prepared through the method can serve as an important chemical engineering and medical intermediate, has the biological activity and is suitable for preparing colon cancer resisting drugs.

Description

technical field [0001] The invention relates to the field of synthetic medicine and chemical industry, and mainly relates to a C-3 fully substituted oxindole derivative and its rapid and highly selective chemical synthesis method and application. Background technique [0002] Oxindole derivatives are indispensable and important skeleton structural units for natural products and synthetic important drugs. Many marine organisms and fungal metabolites contain such skeleton structures, which have antibacterial, antitumor, anticancer and enzyme inhibitory properties. Biological activity, so the research on its synthesis method has always been a hot topic in the field of natural heat product research and medicinal chemistry. In recent years, chemists have also discovered many synthetic methods of oxidindole derivatives, such as when Overman synthesized gliocladine C (Gliocladine C), using Fu catalysis (Angew.Chem.Int.Ed., 2003, 42,3921-3924) to obtain the structural framework of ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D209/34A61K31/405A61P35/00
CPCC07D209/34
Inventor 胡文浩杨杨雷锐锐马超群刘顺英李自岩
Owner EAST CHINA NORMAL UNIV
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