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3-(2,2-dimethyl) propionitrile-3-alkyl (aryl) indolone and preparation method thereof

A technology of dimethyl and propylcyano, which is applied in the field of simple synthesis, drug construction skeleton 3-propylcyano-3-alkylindolinone and its low cost, and can solve the problems of inability to synthesize

Inactive Publication Date: 2015-07-08
JISHOU UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

It is particularly worth noting that this reported method cannot synthesize 3-(2,2-dimethyl)propylcyano-3-alk(aryl)ylindole, which contains a tertiary cyanide structure. ketone

Method used

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  • 3-(2,2-dimethyl) propionitrile-3-alkyl (aryl) indolone and preparation method thereof
  • 3-(2,2-dimethyl) propionitrile-3-alkyl (aryl) indolone and preparation method thereof
  • 3-(2,2-dimethyl) propionitrile-3-alkyl (aryl) indolone and preparation method thereof

Examples

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Effect test

preparation example 1

[0031] The preparation of raw material B, taking the preparation of N-methyl-N-phenyl 2-methacrylamide as an example

[0032]

[0033] N-Methyl-N-phenyl 2-methacrylamide

[0034] Add 2-methacrylic acid (15mmol) and dry dichloromethane 20mL in a 100mL round-bottomed flask, then stir the mixture for 5min in ice bath, add 3-5 drops of DMF (N,N-dimethylformamide ), then slowly add equivalent oxalyl chloride (16.5mmol) dissolved in 5-10mL of dry dichloromethane, and then react at 0°C for 1h (opening the reaction system is conducive to the volatilization of hydrogen chloride gas generated). Then, under ice-bath conditions, triethylamine (30mmol, 2eq) dissolved in a small amount of dry dichloromethane was added, followed by aniline (10mmol, also dissolved in a small amount of dry methylene chloride, reacted in a closed system at room temperature for 1-2h. The mixture was washed with saturated brine, filtered, and the filtrate was distilled off to obtain a crude product. Using eth...

Embodiment 1

[0055] Preparation of target product A, taking the preparation of 3-(2,2-dimethyl)propylcyano-1,3-dimethylindol-2-one as an example

[0056]

[0057] Add N-methyl-N-phenyl-β-methyl-acrylamide (0.5mmol.0.052g), azobisisobutylcyanide AIBN (1.0mmol, 0.164g) and copper iodide successively in a round bottom flask (0.002mmol, 0.004g), acetonitrile (2mL), and finally add di-tert-butyl peroxide DTBP (1.0mmol, 0.146g), react at 80°C, after the reaction (usually 3-5 hours) , ethyl acetate was added, and then washed with brine, and the aqueous phase was extracted with ethyl acetate. The organic phase was collected, dried, concentrated, and separated by column chromatography to obtain the product 3-(2,2-dimethyl)propylcyano-1,3-dimethylindol-2-one, a colorless solid, melting point : 89-90°C, yield 75%.

[0058] Structure Characterization: 1 H NMR (400MHz, CDCl 3 )δ7.40-7.25 (m, 2H), 7.09 (t, J = 6.0Hz, 1H), 6.90 (d, J = 6.4Hz, 2H), 3.23 (s, 3H), 2.32 (d, J = 11.6 Hz,1H),2.16(d,J=1...

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Abstract

3-(2,2-dimethyl) propionitrile-3-alkyl (aryl) indolone with a following formula is prepared by a series addition / C-H cyclization reaction of reaction substrates of N-aryl acrylamide with a formula B and azodiisobutyronitrile (AIBN) in a reaction solution in the presence of a catalyst copper halide (such as copper iodide or bromide copper) and an oxidation agent of organic peroxide (such as di-tert-butyl peroxide).

Description

technical field [0001] The invention relates to a class of important drug construction skeleton 3-(2,2-disubstituted) propanylcyano-3-alk(aryl)indolinone and a cheap and convenient synthesis method thereof. Background technique [0002] Among many heterocyclic compounds, indolinones and their derivatives have attracted widespread attention due to their remarkable pharmacological and biological activities. They widely exist in many natural products and are the active ingredients and symbolic ingredients of a variety of plants. For example, the active ingredient (E)-dimethoxindolinone is extracted and isolated from the Chinese medicine Radix Isatidis, and is isolated from the Chinese medicine Daqingye. The active ingredient 6-hydroxy-2-indolinone is extracted, and the active ingredient (E)-3-(3-methyl-2-butenylene)-2-indolinone is separated and extracted from the traditional Chinese medicine Xing'an Cimicifuga, And the active ingredient 5-hydroxy-2-indolinone was extracted an...

Claims

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Application Information

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IPC IPC(8): C07D209/34A61P35/00A61P29/00
CPCC07D209/34
Inventor 唐石周栋李自豪邓佑林黎淑华
Owner JISHOU UNIVERSITY
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