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Synthesis method of polysubstituted isoindoline derivative

A technology of isoindolinone and a synthesis method, applied in the field of organic synthesis, can solve the problems of complicated steps, difficult source of raw materials, high price, etc., and achieves the effects of good reaction universality, convenient source of raw materials, and good promotion prospect.

Active Publication Date: 2018-03-27
CHANGZHOU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] In the existing synthesis methods of isoindolinone derivatives, the sources of raw materials involved are often difficult and expensive, and some raw materials are relatively toxic and dangerous, and there are great safety hazards in the preparation process; The conditions required for the reaction are relatively complex and the steps are cumbersome; the prepared product is less selective when it is substituted and derivatized

Method used

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  • Synthesis method of polysubstituted isoindoline derivative
  • Synthesis method of polysubstituted isoindoline derivative
  • Synthesis method of polysubstituted isoindoline derivative

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0020] Synthesis of Isoindolinone Derivative 1

[0021]

[0022] Benzoyl chloride (5mmol), o-aminophenol (10mmol), methyl acrylate (5mmol), [Rh(cod)Cl] 2 (0.05mmol), AgSbF 6 (0.1mmol), copper acetate (2mmol), sodium hydroxide (10mmol) and acetonitrile (5mL) were added to the reaction tube, mixed thoroughly and heated to 60 ° C and kept for 24 hours; after the reaction, the resulting mixture was poured into ice water, extracted with ethyl acetate, fully washed with deionized water, dried, and distilled under reduced pressure to obtain a crude product. Through TLC spot plate analysis, there were no obvious by-products except the remaining raw materials, and almost only one new substance was produced. Chromatography obtained 1.04g of pure product, with a yield of 70% (the yield is based on the molar weight of aroyl chloride in the raw material, the same below), and was detected as the target product by mass spectrometry and carbon spectrometry:

[0023] 1 H NMR (300MHz, CDC...

Embodiment 2

[0025] Synthesis of Isoindolinone Derivative 2

[0026]

[0027] P-toluoyl chloride (5mmol), o-aminophenol (10mmol), methyl acrylate (15mmol), [Cp*RhCl 2 ] 2 (0.25mmol), AgSbF 6 (2mmol), copper acetate (5mmol), potassium carbonate (10mmol) and acetonitrile (50mL) were added to the reaction tube, after mixing thoroughly, the temperature was raised to 120°C and kept for 6 hours; after the reaction, the resulting mixture was poured into ice In water, extracted with ethyl acetate, fully washed with deionized water, dried, and distilled under reduced pressure to obtain a crude product. Through TLC spot plate analysis, there were no obvious by-products except the remaining raw materials, and almost only one new substance was formed. After column chromatography Obtain 1.48g of pure product, the yield is 95%, and it is the target product detected by mass spectrometry and carbon spectrometry:

[0028] 1 H NMR (300MHz, DMSO-d6) δ9.78(s, 1H), 7.64(d, J=7.7Hz, 1H), 7.44(s, 1H), 7.3...

Embodiment 3

[0030] Synthesis of Isoindolinone Derivative 3

[0031]

[0032] P-chlorobenzoyl chloride (5mmol), o-aminophenol (10mmol), methyl acrylate (10mmol), [RuCl 2 (p-Cymene)] 2 (0.1mmol), AgBF 4 (0.4mmol), copper acetate (3mmol), triethylamine (10mmol)

[0033] -3-

[0034] and acetonitrile (10mL) were added to the reaction tube, mixed thoroughly, heated to 100°C and kept for 12 hours of reaction; after the reaction, the resulting mixture was poured into ice water, extracted with ethyl acetate, fully washed with deionized water, and dried. The crude product was obtained by distillation under reduced pressure. Through TLC spot plate analysis, there were no obvious other by-products except the remaining raw materials, and almost only a new substance was generated. The pure product was 1.36g through column chromatography, and the yield was 82%. After mass spectrometry, carbon Spectral detection for the target product:

[0035] 1 H NMR (300MHz, CDCl 3 )δ8.09(s,1H),7.86(d,J=8.1...

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Abstract

The invention belongs to the field of organic synthesis and in particular relates to a synthesis method of a polysubstituted isoindoline derivative. The synthesis method comprises the following steps:after sufficiently mixing aryl chloride, o-aminophenol, olefin with an electron withdrawing group, a catalyst, an additive, an oxidant, an alkali and a solvent, raising temperature and reacting; after reaction is finished, carrying out post-treatment to obtain a target product.

Description

technical field [0001] The invention belongs to the field of organic synthesis, in particular to a method for synthesizing polysubstituted isoindolinone derivatives. Background technique [0002] Isoindolinone derivatives are a class of important organic intermediates. Some of these compounds have good antitumor activity and antibacterial activity, and are widely used in the field of medicine. [0003] In the existing synthesis methods of isoindolinone derivatives, the sources of raw materials involved are often difficult and expensive, and some raw materials are relatively toxic and dangerous, and there are great safety hazards in the preparation process; The conditions required for the reaction are relatively complicated and the steps are cumbersome; when the prepared product is substituted and derivatized, the selectivity is small. Therefore, it is necessary to develop a simple and efficient method for preparing isoindolinone derivatives. Contents of the invention [...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D209/46
CPCC07D209/46
Inventor 王亮周楷翔何明阳
Owner CHANGZHOU UNIV
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