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Synthesis method for 3-thioether isoindolinone compound

A technology for isoindolinone and ketone compounds, which is applied in the field of synthesis of 3-sulfide isoindolinone compounds, can solve problems such as expensive catalysts, complex catalyst structures, difficult synthesis reaction conditions, etc., to avoid The effect of expensive catalyst, simple raw materials and reagents, and easy operation

Active Publication Date: 2019-11-12
山东济清科技服务有限公司
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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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  • Synthesis method for 3-thioether isoindolinone compound
  • Synthesis method for 3-thioether isoindolinone compound
  • Synthesis method for 3-thioether isoindolinone compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0024]

[0025] In the round bottom flask of 100mL, add 2.39g (10mmol) compound I-1, 1.24g (20mmol) compound II-1, 0.26g (1mmol) solid Ni(ClO 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 50mL×3 methylene chloride, and the extracted organic phases were combined, washed once with saturated brine, anhydrous Na 2 SO 4 Dry, filter, concentrate and remove the solvent to obtain a crude product, which is separated by column chromatography to obtain a pure product of compound III-1. Oily liquid, 2.60g, yield 92%. 1 HNMR (400MHz, CDCl 3 )δ: 7.87(d, J=7.5Hz, 1H), 7.57(s, 2H), 7.51–7.44(m, 1H), 7.30(dq, J=13.7Hz, 7.3Hz, 5H), 5.38(d, J=14.7Hz, 1H), 5.28(s, 1H), 4.39(d, J=14.7Hz, 1H), 1.96(dd, J=12.3Hz, 7.5Hz, 1H), 1.87–1.79(m, 1H) ,0.96(t,J=7.5Hz,3H); 13 C NMR (CDCl 3 ,100MHz)δ:167.33,143.66,136.91,...

Embodiment 2

[0027]

[0028] In the round bottom flask of 100mL, add 2.39g (10mmol) compound I-1, 1.52g (20mmol) compound II-2, 0.26g (1mmol) solid Ni(ClO 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 50mL×3 dichloromethane, combined and extracted organic phases, washed once with saturated brine, anhydrous Na 2 SO 4 Dry, filter, concentrate and remove the solvent to obtain a crude product, which is separated by column chromatography to obtain a pure product of compound III-2. Oily liquid, 2.67g, yield 90%. 1 HNMR (400MHz, CDCl 3 )δ7.87(d, J=7.5Hz, 1H), 7.57(d, J=12.6Hz, 2H), 7.52–7.43(m, 1H), 7.29(ddd, J=22.2Hz, 13.8Hz, 6.9Hz ,5H),5.37(d,J=14.7Hz,1H),5.27(s,1H),4.39(d,J=14.7Hz,1H),1.90(dt,J=12.3Hz,7.4Hz,1H), 1.82–1.69(m,1H),1.28(dt,J=14.5Hz,7.2Hz,2H),0.80(t,J=7.3Hz,3H); 13 C NMR (CDCl 3 ,10...

Embodiment 3

[0030]

[0031] In the round bottom flask of 100mL, add 2.39g (10mmol) compound I-1, 1.35g (15mmol) compound II-3, 0.09g (0.5mmol) solid Ni(NO 3 ) 2 , and finally 50 mL of dry DMSO was added, and the resulting mixture was stirred vigorously at 120° C. for 5 hours. After the reaction mixture was cooled to room temperature, it was poured into water, stirred, extracted with 50mL×3 dichloromethane, combined and extracted organic phases were washed once with saturated brine, anhydrous Na 2 SO 4 Dry, filter, concentrate and distill off the solvent to obtain a crude product, which is purified by column chromatography to obtain a pure product of compound III-3. Oily liquid, 2.58g, yield 87%. 1 HNMR (400MHz, CDCl 3 )δ: 7.87(d, J=7.5Hz, 1H), 7.60–7.51(m, 2H), 7.51–7.44(m, 1H), 7.30(ddd, J=22.5Hz, 13.9Hz, 7.0Hz, 5H) ,5.37(d,J=14.7Hz,1H),5.28(s,1H),4.37(d,J=14.7Hz,1H),1.80(dd,J=12.0Hz,6.7Hz,1H),1.63(dd ,J=11.9Hz,6.9Hz,1H),1.46(dt,J=13.3Hz,6.7Hz,1H),0.81(t,J=6.2Hz,6H); 13 C NMR (CD...

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Abstract

The invention provides a synthesis method for a 3-thioether isoindolinone compound. The synthesis method comprises the following steps: catalyzing a 3-hydroxyl -2-phenmethyl-isoindoline-1-one compoundand a thiol compound by using Ni (II) to generate imine cation in situ, and performing a nucleophilic addition reaction, so as to obtain 3-thioether isoindolinone, wherein the product yield is 82-95%. The method is completed at one step, is simple in operation, simple in raw material and reagent, high in reaction yield, capable of avoiding defects that a conventional method is high in catalyst price and harsh in condition and easy in product separation and purification, has great values for research on synthesis of 3-thioether isoindolinone compounds, and has great significances for synthesisof sulfur-containing natural products and medicine molecules.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis, and in particular relates to a synthesis method of 3-sulfide isoindolinone compounds. Background technique [0002] 3-thioetherisoindolinones are a class of very active and important intermediates that are widely used in natural product and medicinal chemistry. Because 3-thioether-isoindolinone compounds are widely used, the research on their preparation methods has always been the focus of attention of organic synthesis experts. Now there are many ways to prepare such compounds: such as noble metal catalysis, acidic, basic conditions, etc., the reaction conditions are relatively harsh. Most of the existing reaction methods are either expensive, or not suitable for the preparation of compounds containing acid-base sensitive functional groups, and the system needs to be neutralized to neutral after the reaction, and the post-treatment operation is cumbersome. [0003] The construction ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D209/46
CPCC07D209/46
Inventor 楼建芳范理鹏刘伟谭学杰张硕
Owner 山东济清科技服务有限公司
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