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A method for the continuous photo-induced catalytic synthesis of pyrrolidone compounds

A technology of amine compounds and compounds, applied in chemical instruments and methods, chemical/physical processes, chemical/physical/physical chemical processes, etc., can solve problems such as low reaction efficiency and large metal residues, and achieve uniform illumination and metal-free Residue, high yield effect

Active Publication Date: 2021-09-24
NANJING TECH UNIV
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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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  • A method for the continuous photo-induced catalytic synthesis of pyrrolidone compounds
  • A method for the continuous photo-induced catalytic synthesis of pyrrolidone compounds
  • A method for the continuous photo-induced catalytic synthesis of pyrrolidone compounds

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Experimental program
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Effect test

Embodiment 1

[0043]At room temperature, 5,10-bis(4-(trifluoromethyl)phenyl)-5,10-dihydrophenazine (23.5 mg, 50 μmol, 5% equivalent), 2-bromo-2-methylpropane Ethyl acetate (294.0 μL, 2 mmol, 2 equivalents), aniline (91.1 μL, 1 mmol, 1 equivalent) and styrene (116.8 μL, 1 mmol, 1 equivalent) were dissolved in the solvent DCE (4 mL), and stirred with a stirring bar, Exposure to simulated sunlight for 4 hours. The eluent of petroleum ether and ethyl acetate 10:1 (volume ratio) was used to separate, and the obtained product was vacuum-dried for 4 h. 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, 39.304, 25 18 h 19 NO[M+H + ]: 266.1539; measured value: 266.1508.

Embodiment 2

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

Embodiment 3

[0049] 5,10-Bis(4-(trifluoromethyl)phenyl)-5,10-dihydrophenazine (23.5 mg, 50 μmol, 5% equiv) was dissolved in solvent DCE (2 mL) at room temperature to give The first homogeneous solution; ethyl 2-bromo-2-methylpropanoate (294.0 μL, 2 mmol, 2 equiv), aniline (91.1 μL, 1 mmol, 1 equiv) and styrene (116.8 μL, 1 mmol, 1 equiv ) was dissolved in the solvent DCE (2mL) to obtain the second homogeneous solution; then the above-mentioned first second homogeneous solution was pumped into the microchannel reactor, and the control pump flow rate was 0.05mL / min. In the microchannel reactor, the retention time is 10 min; the effluent liquid is collected with a sampling flask. The eluent of petroleum ether and ethyl acetate 10:1 (volume ratio) was used to separate, and the obtained product was vacuum-dried for 4 h. The conversion rate was 96%. NMR see 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,1H...

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Abstract

The invention discloses a method for continuously photo-induced catalytically synthesizing pyrrolidone compounds. Organic catalysts, olefinic organic compounds, bromoacetate compounds and amine compounds are dissolved in a solvent to obtain a homogeneous solution; The homogeneous solution is pumped into a microchannel reaction device provided with a light source for reaction to obtain a reaction solution containing pyrrolidone compounds. Compared with the prior art, the invention replaces the catalyst by organic photocatalysis, is green and efficient, has no metal residue, and has wide application prospects in the synthesis of medical products.

Description

technical field [0001] The invention relates to the field of medicinal chemistry and fine chemical synthesis, in particular to a method for continuous light-induced catalytic synthesis of pyrrolidone compounds Background technique [0002] Pyrrolone compounds have a special structure similar to indole, azaindole, etc. and good biological activity, and have a wide range of applications in the pharmaceutical and agricultural chemical industries (such as the treatment of cancer, the treatment of viral hepatitis B, the treatment of heart disease, etc.) . [0003] At present, metal catalysts (Pd, Fe, Cu, Ni, Co, Au) are generally used to catalyze cyclization to synthesize pyrrolidone compounds, but there are often problems such as high reaction temperature, long reaction time, low yield, and limited metal residues. Its application in medicine and other fields. [0004] In recent years, the difunctionalization reaction of alkenes has been developed rapidly. This reaction can not...

Claims

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Application Information

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Patent Type & Authority Patents(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 TECH UNIV
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