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1,3-dihydro-2H-pyrrolidone compounds and synthetic method thereof

A compound, pyrrolidone technology, applied in the field of 1,3-dihydro-2H-pyrrolidone compound and its synthesis, can solve limitations and other problems, achieve high selectivity and yield, and good industrial application prospects

Active Publication Date: 2016-10-12
重庆市化工研究院有限公司 +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Although these methods can effectively synthesize pyrrolidone compounds, these methods have certain limitations: some reactions are limited to specific substituents; some reactions require multi-step synthesis; some use transition noble metal catalysts; Only react at higher temperature or under microwave conditions

Method used

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  • 1,3-dihydro-2H-pyrrolidone compounds and synthetic method thereof
  • 1,3-dihydro-2H-pyrrolidone compounds and synthetic method thereof
  • 1,3-dihydro-2H-pyrrolidone compounds and synthetic method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0027] Synthesis of 1-(Benzyloxy)-3,3-dimethyl-5-phenyl-1,3-dihydro-2H-pyrrol-2-one

[0028] Add 0.25 mmol of K to the reaction vessel 2 CO 3 , 0.1mmol phenylacetylene, then add 1ml trifluoromethanol, 0.12mmol α-halogenated amide (N-(benzyloxy)-2-bromo-2-methylpropionamide), react at 25°C, after the reaction, wash with aqueous solution , and then extracted with an organic solvent, dried, concentrated under reduced pressure to remove the solvent, and the crude product was separated by column chromatography to obtain the target product with a yield of 70%.

Embodiment 2

[0030] Synthesis of 1-(benzyloxy)-5-(4-methoxyphenyl)-3,3-dimethyl-1,3-dihydro-2H-pyrrol-2-one

[0031] Add 0.15 mmol of KOH, 0.1 mmol of 4-methoxyphenylacetylene to the reaction vessel, then add 1 ml of trifluoroethanol, 0.11 mmol of α-halogenated amide (N-(benzyloxy)-2-bromo-2-methylpropane Amide) was reacted at 25°C. After the reaction was completed, it was washed with an aqueous solution, then extracted with an organic solvent, dried, and evaporated under reduced pressure to remove the solvent. The crude product was separated by column chromatography to obtain the target product with a yield of 55%.

Embodiment 3

[0033] Synthesis of 1-(benzyloxy)-5-(4-fluorophenyl)-3,3-dimethyl-1,3-dihydro-2H-pyrrol-2-one

[0034] Add 0.15 mmol of NaOH, 0.1 mmol of 4-fluorophenylacetylene to the reaction vessel, then add 1 ml of acetonitrile, 0.12 mmol of α-halogenated amide (N-(benzyloxy)-2-bromo-2-methylpropionamide), 25 ℃ reaction, after the reaction, wash with aqueous solution, then extract with organic solvent, dry, evaporate and concentrate under reduced pressure to remove the solvent, and the crude product is separated by column chromatography to obtain the target product with a yield of 57%.

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Abstract

The invention discloses 1,3-dihydro-2H-pyrrolidone compounds and a synthetic method thereof. A solvent and an alkali are added to a container containing substituted alpha-halogenated amide and a substituted alkyne compound, the mixture is stirred at the reaction temperature of 25-100 DEG C, a product is washed with water or a salt solution after the reaction and then extracted with an organic solvent, an extraction product is dried and distilled at reduced pressure to remove the solvent, a crude product is subjected to column chromatography separation, and the target product, namely, the 1,3-dihydro-2H-pyrrolidone compounds are obtained. The method has the advantages that no transition metal catalyst is used, the raw materials are cheap and available, reaction substrates are highly adaptable, reaction conditions are mild, regioselectivity is good, the yield is high, environmental protection is realized and the like, and has good industrial application prospect.

Description

technical field [0001] The invention relates to the field of organic synthesis, in particular to a 1,3-dihydro-2H-pyrrolone compound and a synthesis method thereof. Background technique [0002] Pyrrolone compounds widely exist in natural products, synthetic drugs and agricultural chemicals. These compounds have good biological activity and pharmaceutical activity, and they are widely used in antibacterial, antiviral, anti-inflammatory, anti-senile dementia, anti-epilepsy and so on. Therefore, the synthesis of pyrrolidone compounds has always attracted the attention of pharmacologists, biologists and chemists. [0003] There are many synthetic methods of pyrrolone compounds: the reaction of substituted 2,5-dicarbonyl compounds and amines; the reaction of substituted enamines and substituted enones; the reaction of maleic anhydride and substituted enamines; The reaction of hydrogen amides and sulfur ylides; Pd, Ru, Rh, Au, Ag and other noble metal catalysts catalyze the rea...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D207/38C07D409/04
CPCC07D207/38C07D409/04
Inventor 汪钢强杨甜宏蒋龙强孙绍发汪舰
Owner 重庆市化工研究院有限公司
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