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A simple way to synthesize 3-ether-based pheasin ketones

A technology for isoindolinone and compounds, which is applied in the field of synthesizing 3-ether isoindolinone compounds, can solve problems such as difficult synthesis reaction conditions, complex catalyst structure, expensive catalyst, etc., and avoid complex methods and raw materials and the effect of simple reagents and high reaction yield

Active Publication Date: 2022-08-09
山东济清科技服务有限公司
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

For example Au(I) / Ag(I), Sn(NTf) 4 and Pd(II)-Ag(I) catalytic system, etc., but the existing synthetic methods have limitations: the catalyst used is expensive, the catalyst structure is more complex and difficult to synthesize or requires harsher reaction conditions, so it is urgent to develop a simple Efficient Synthetic Method for Forming Imide Ions

Method used

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  • A simple way to synthesize 3-ether-based pheasin ketones
  • A simple way to synthesize 3-ether-based pheasin ketones
  • A simple way to synthesize 3-ether-based pheasin ketones

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0020]

[0021] 2.39g (10mmol) of compound I-1, 0.64g (20mmol) of compound II-1, 0.26g (1mmol) of solid Ni(ClO) were added to a 100mL round-bottomed flask 4 ) 2 , and finally 20 mL of dry 1,2-dichloroethane was added, and the resulting mixture was stirred at 80 °C for 10 hours. After the reaction mixture was cooled to room temperature, it was poured into ice water, extracted with 50 mL×3 dichloromethane, the organic phases were combined and extracted, washed once with saturated brine, and anhydrous Na 2 SO 4 Dry, filter, and concentrate to remove the solvent to obtain the crude product, which is separated by column chromatography to obtain the pure product of compound III-1. Oily liquid, 2.40 g, 95% yield. 1 H NMR (400MHz, CDCl 3 )δ: 7.87(d, J=7.1Hz, 1H), 7.60–7.45 (m, 3H), 7.40–7.21 (m, 5H), 5.71 (s, 1H), 5.19 (d, J=14.7Hz, 1H) ), 4.21(d, J=14.7Hz, 1H), 2.88(s, 3H); 13 CNMR (CDCl 3 ,100MHz)δ:167.48,140.47,136.87,132.99,132.10,129.97,128.72,128.65,128.63,127.65,123.6...

Embodiment 2

[0023]

[0024] 2.39g (10mmol) of compound I-1, 0.92g (20mmol) of compound II-2, 0.26g (1mmol) of solid Ni(ClO) were added to a 100mL round-bottomed flask 4 ) 2 , and finally 25 mL of dry DMF was added, and the resulting mixture was stirred at 100° C. for 5 hours until the reaction was complete. The reaction mixture was cooled to room temperature, poured into water, stirred, extracted with 50 mL×3 dichloromethane, combined and extracted with organic phases, washed once with saturated brine, and anhydrous Na 2 SO 4 Dry, filter, and concentrate to remove the solvent to obtain the crude product, which is separated by column chromatography to obtain the pure product of compound III-2. Oily liquid, 2.62 g, 98% yield. 1 HNMR (400MHz, CDCl 3 )δ7.86(d,J=7.1Hz,1H),7.60–7.45(m,3H),7.31(ddd,J=22.6Hz,16.7Hz,6.9Hz,5H),5.71(s,1H),5.15 (d, J=14.7Hz, 1H), 4.27 (d, J=14.7Hz, 1H), 3.15 (dq, J=14.2Hz, 7.1Hz, 1H), 2.99 (dd, J=15.9Hz, 7.1Hz, 1H), 1.09 (t, J=7.0Hz, 3H); 13 C NMR (CDCl 3 ...

Embodiment 3

[0026]

[0027] 2.39g (10mmol) of compound I-1, 1.35g (15mmol) of compound II-3, 0.09g (0.5mmol) of solid Ni(NO) were added to a 100mL round-bottomed flask 3 ) 2 , and finally 50 mL of dry DMSO was added, and the resulting mixture was vigorously stirred at 120 °C for 5 hours. After the reaction mixture was cooled to room temperature, it was poured into water, stirred, extracted with 50 mL×3 dichloromethane, the organic phases were combined and extracted, washed once with saturated brine, and anhydrous Na 2 SO 4 Dry, filter, concentrate and evaporate the solvent to obtain the crude product, which is purified by column chromatography to obtain the pure product of compound III-3. Oily liquid, 2.70 g, 88% yield. 1 H NMR (400MHz, CDCl 3 )δ: 7.85(d, J=7.1Hz, 1H), 7.51(ddd, J=17.5Hz, 11.9Hz, 7.1Hz, 3H), 7.37–7.22(m, 5H), 5.64(s, 1H), 5.25 (d, J=14.9Hz, 1H), 4.24 (d, J=14.9Hz, 1H), 3.92–3.70 (m, 1H), 1.76–1.62 (m, 4H), 1.45 (ddt, J=15.2Hz, 12.3Hz, 7.7Hz, 4H); 13 C NMR (CDCl3...

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Abstract

The invention provides a simple method for synthesizing 3-ether-based isoindolinone compounds, which comprises Ni( II) catalyzing in-situ generation of imine cations and nucleophilic addition reaction to construct 3-ether isoindolinone compounds, the product yield is 88%-98%. The method is completed in one step, the operation is simple, the raw materials and reagents are simple, the reaction yield is high, the disadvantages of expensive catalysts and harsh conditions of the traditional method are avoided, the product is easy to be separated and purified, and the synthesis of 3-ether isoindolinone compounds Methodological research is of great value and is of great significance in the total synthesis of natural products and drug synthesis.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis, in particular to a simple method for synthesizing 3-ether isoindolinone compounds. Background technique [0002] Compounds containing isoindolinone skeletons are a very important class of nitrogen-containing heterocyclic compounds, which widely exist in a variety of natural products. In addition, due to their important biological activities, such as antioxidant, antiviral and antibacterial, the synthesis of compounds containing isoindolinone structural units has received extensive attention. A large number of synthetic methods for isoindolinone derivatives have been been reported. Condensation of o-halomethyl or o-acyl benzoates with amines is a traditional method for the synthesis of isoindolinones, selective reduction of phthalimides and benzopyrrolone derivatives A variety of organic transformations have also been used to synthesize isoindolinone derivatives. However, in view of t...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D209/48
CPCC07D209/48
Inventor 楼建芳闫志旺谭学杰张硕
Owner 山东济清科技服务有限公司