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A kind of preparation method of ether substituted 2-pyrrolidone compound

A pyrrolidone and compound technology, applied in the field of preparation of 2-pyrrolidone compounds, can solve the problems of low reaction selectivity, low reaction efficiency, and uneconomical reaction system, and achieve simple and efficient reaction process, high selectivity, and atom economy And the effect that the step economy is high

Active Publication Date: 2022-02-01
YANGTZE NORMAL UNIVERSITY
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0007] In view of the above-mentioned deficiencies in the prior art, the purpose of the present invention is to: provide a new preparation method for ether-substituted 2-pyrrolidone compounds, and then provide a basis for the activity research and application of ether-substituted 2-pyrrolidone compounds At the same time, it also solves the problems of low reaction selectivity, uneconomical reaction system and low reaction efficiency in the cyclization reaction of existing 1,6-diene compounds

Method used

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  • A kind of preparation method of ether substituted 2-pyrrolidone compound
  • A kind of preparation method of ether substituted 2-pyrrolidone compound
  • A kind of preparation method of ether substituted 2-pyrrolidone compound

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Experimental program
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Effect test

Embodiment 1

[0025]

[0026] Add the 1,6-diene compound (40.2 mg, 0.2 mmol) represented by formula 1a, tetrahydrofuran (2 mL) represented by formula 2a and tert-butyl peroxybenzoate (TBPB, 77.7 mg, 2 eq. 2 times the number of moles of 1,6-diene compound, the same below), then the reactor was stirred and reacted in an air atmosphere at 120°C, and the reaction process was monitored by TLC until the raw materials disappeared (reaction time was 6 hours), and the reaction After completion, the reaction solution was extracted with ethyl acetate, the organic phase was dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure to remove the solvent, and the residue was separated by column chromatography (elution solvent: ethyl acetate / n-hexane ) to obtain the target product (78% yield, d.r.>20:1).

[0027] Detection of target products:

[0028] 1 H NMR (500MHz, CDCl 3 )δ:7.64-7.62(m,2H),7.36-7.33(m,2H),7.11(t,J=7.5Hz,1H),4.11-4.06(m,1H),3.89-3.80(m,2H) ,3.70-3.65(...

Embodiment 2

[0031]The oxidizing agent is tert-butyl peroxybenzoate (TBHP) instead of tert-butyl peroxybenzoate, and all the other conditions are the same as in Example 1, and the yield of the target product I-1 is 80%.

Embodiment 3

[0033] The oxidizing agent used di-tert-butyl peroxide (DTBP) instead of tert-butyl peroxybenzoate, and the remaining conditions were the same as in Example 1, and the yield of the target product I-1 was 15%.

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Abstract

The present invention relates to a kind of preparation method of ether-substituted 2-pyrrolidone compound, the method adds 1,6-diene compound, ether solvent and oxidant into schlenk bottle, then above-mentioned reactor is stirred and reacted under air atmosphere , after the reaction is completed, the target product is obtained through post-processing. The process can be realized only at high temperature without catalyst and alkali, avoids the generation of other free radicals, greatly improves the reaction yield, and shortens the reaction time. The invention has the advantages of simple operation, cheap and easy-to-obtain raw materials, mild reaction conditions, high efficiency and stability, high atom economy and step economy, is especially suitable for industrial production, has good application prospects, and is an ether-substituted 2-pyrrolidone compound It provides a basis for the research and application of the activity of , and also provides a new idea for the free radical cyclization reaction.

Description

technical field [0001] The invention relates to the technical field of organic synthesis, in particular to a preparation method of ether-substituted 2-pyrrolidone compounds. Background technique [0002] Pyrrolidone compounds are a class of pyrrolidine compounds with a five-membered lactam ring, which widely exist in natural products and various synthetic compounds. It is worth emphasizing that many natural products and synthetic compounds containing pyrrolidone structural units All have strong biological activity and are widely used in the field of medicine. For example, the invention patent CN104800209A discloses that pyrrolidone compounds can be used as bidirectional target inhibitors of acetylcholinesterase (AChE) and β-secretase (BACE1) for the preparation of drugs for the treatment of Alzheimer's disease, and the pyrrolidone compounds with the following structure have been verified. [0003] [0004] Due to the rich biological activities of pyrrolidones, developing...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D405/06
CPCC07D405/06
Inventor 陈锦杨吴燕梅兰钟春涛陈睿
Owner YANGTZE NORMAL UNIVERSITY
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