Method for synthesizing pyrrolidone compound through continuous light-induced catalysis

An amine compound and compound technology, which is applied in chemical instruments and methods, chemical/physical processes, chemical/physical/physical chemical processes, etc., can solve the problems of large metal residues and low reaction efficiency, and achieve no metal residues and light exposure. Uniform, high-yield effect

Active Publication Date: 2020-10-16
NANJING UNIV OF TECH
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0006] Purpose of the invention: The technical problem to be solved by the present invention is to provide a method for continuous light-induced catalytic synthesis of pyrrolidone compounds to solve the problems of low reaction efficiency and large metal residues in the prior art.

Method used

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  • Method for synthesizing pyrrolidone compound through continuous light-induced catalysis
  • Method for synthesizing pyrrolidone compound through continuous light-induced catalysis
  • Method for synthesizing pyrrolidone compound through continuous light-induced catalysis

Examples

Experimental program
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Effect test

Embodiment 1

[0043] At room temperature, 5,10-bis(4-(trifluoromethyl)phenyl)-5,10-dihydrophenazine (23.5mg, 50μmol, 5% equivalent), 2-bromo-2-methylpropane Ethyl acid (294.0μL, 2mmol, 2 equivalents), aniline (91.1μL, 1mmol, 1 equivalent) and styrene (116.8μL, 1mmol, 1 equivalent) were dissolved in the solvent DCE (4mL) and stirred with a stirring bar. Irradiate under simulated sunlight for 4h. Separate with petroleum ether and ethyl acetate 10:1 (volume ratio) eluent, and vacuum dry the obtained product for 4h. The conversion rate was 86%.

[0044] 1 H NMR(400MHz, Chloroform-d) δ7.42–7.25(m,7H), 7.24–7.01(m,3H), 5.42(dd,J=10.2,6.0Hz,1H),2.43(dd,J=12.7 ,6.0Hz,1H),2.04(s,1H),1.44(d,J=13.4Hz,6H). 13 CNMR (101MHz, Chloroform-d) δ139.20,127.70,127.59,127.53,127.32,127.08,124.39,124.29,122.52,121.71,121.67,121.43,79.14,45.06,40.83,39.74,25.30,25.18.HRMS calculated value C 18 H 19 NO[M+H + ]: 266.1539; Found: 266.1508.

Embodiment 2

[0046] At room temperature, 5,10-bis(4-(trifluoromethyl)phenyl)-5,10-dihydrophenazine (23.5mg, 50μmol, 5% equivalent), 2-bromo-2-methylpropane Ethyl acid (294.0μL, 2mmol, 2 equivalents), aniline (91.1μL, 1mmol, 1 equivalent) and styrene (116.8μL, 1mmol, 1 equivalent) were dissolved in the solvent DCE (4mL) to obtain a homogeneous solution. The above-mentioned homogeneous solution was pumped into the microchannel reactor, and the flow rate of the pump was controlled to be 0.1 mL / min. In the microchannel reactor under simulated sunlight, the retention time was 10min; the effluent liquid was collected with a sampling flask. Separate with petroleum ether and ethyl acetate 10:1 (volume ratio) eluent, and vacuum dry the obtained product for 4h. The conversion rate is 97%.

[0047] 1 H NMR(400MHz, Chloroform-d) δ7.42–7.25(m,7H), 7.24–7.01(m,3H), 5.42(dd,J=10.2,6.0Hz,1H),2.43(dd,J=12.7 ,6.0Hz,1H),2.04(s,1H),1.44(d,J=13.4Hz,6H). 13 CNMR (101MHz, Chloroform-d) δ139.20,127.70,127.59,127.5...

Embodiment 3

[0049] At room temperature, 5,10-bis(4-(trifluoromethyl)phenyl)-5,10-dihydrophenazine (23.5mg, 50μmol, 5% equivalent) was dissolved in the solvent DCE (2mL) to obtain The first homogeneous solution; ethyl 2-bromo-2-methylpropionate (294.0μL, 2mmol, 2 equivalents), aniline (91.1μL, 1mmol, 1 equivalent) and styrene (116.8μL, 1mmol, 1 equivalent) ) Was dissolved in the solvent DCE (2mL) to obtain a second homogeneous solution; then the above-mentioned first and second homogeneous solution was pumped into the microchannel reactor, and the pump flow rate was controlled to be 0.05mL / min. In the microchannel reactor, the retention time is 10 min; the effluent liquid is collected with a sampling flask. Separate with petroleum ether and ethyl acetate 10:1 (volume ratio) eluent, and vacuum dry the obtained product for 4h. The conversion rate is 96%. NMR figure 2 .

[0050] 1 H NMR(400MHz, Chloroform-d) δ7.42–7.25(m,7H), 7.24–7.01(m,3H), 5.42(dd,J=10.2,6.0Hz,1H),2.43(dd,J=12.7 ,6.0Hz,1...

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Abstract

The invention discloses a method for synthesizing a pyrrolidone compound by continuous light-induced catalysis. The method comprises the following steps: dissolving an organic catalyst, an olefin organic compound, a bromo-acetate compound and an amine compound in a solvent to obtain a homogeneous solution; pumping the homogeneous solution into a micro-channel reaction device provided with a lightsource for reaction to obtain a reaction solution containing the pyrrolidone compound. Compared with the prior art, a catalyst is replaced by organic photocatalysis, so that the method is green, efficient and free of metal residues, and has a wide application prospect in the aspect of synthesizing medical products.

Description

Technical field [0001] The present invention relates to the field of medicinal chemistry and fine chemical synthesis, in particular to a method for continuous light-induced catalytic synthesis of pyrrolone compounds Background technique [0002] Pyrrolone compounds have a special structure and good biological activity similar to indole, azaindole, etc., and have a wide range of applications in the medicine and pesticide industry (for example, treatment of cancer, treatment of hepatitis B virus, treatment of heart disease, etc.) . [0003] At present, metal catalysts (Pd, Fe, Cu, Ni, Co, Au) are generally used to catalyze cyclization to synthesize pyrrolone compounds, but there are often problems of high reaction temperature, long reaction time, low yield, and metal residue restrictions Focus on its application in medicine and other fields. [0004] In recent years, the difunctionalization reaction of olefins has been rapidly developed. This reaction can not only synthesize multi-si...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D207/267B01J19/12B01J19/00
CPCB01J19/0093B01J19/127C07D207/267
Inventor 郭凯魏明辉方正掌亚军朱宁何伟刘成扣
Owner NANJING UNIV OF TECH
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