Electrochemical synthesis method of 3-arylseleno quinolinone compound

The technology of an arylselenoquinolinone and a synthesis method, which is applied in a method field, can solve the problems of increasing the difficulty of product separation and purification, increasing the reaction cost and the like, and achieves the advantages of large-scale production, reduction of recovery steps and wide selectivity. Effect

Active Publication Date: 2020-11-10
HUNAN UNIV OF SCI & ENG
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

This method not only needs to use expensive periododine salt oxidant, but also needs to use 1.2 times the equivalent of diphenyldiselenide as the phenylselenide etherification reagent, which not only increases the reaction cost, but also increases the difficulty of separation and purification of the product

Method used

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  • Electrochemical synthesis method of 3-arylseleno quinolinone compound
  • Electrochemical synthesis method of 3-arylseleno quinolinone compound
  • Electrochemical synthesis method of 3-arylseleno quinolinone compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1～5

[0058] The following examples 1 to 5 all react according to the following reaction equation, mainly to investigate the yield situation of different substrates reacting under optimal conditions:

[0059]

[0060] The specific operation steps are: in a 25mL three-neck round bottom flask, add quinolinone (6mmol), diaryl diselenide (3mmol), potassium iodide (0.9mmol), DMSO (12mL) in sequence, two 15mm×15mm×3mm The RVC electrodes serve as anode and cathode, respectively. The resulting mixture was stirred and reacted under a 12mA direct current at room temperature. The progress of the reaction was followed by thin-layer chromatography, and the reaction time was 10 hours. After the reaction was completed, 12ml of water was added and the product was precipitated, filtered and dried to obtain the pure product.

Embodiment 1

[0062] Compound 1,3-(p-tolylselanyl)quinolin-4(1H)-one, yield 98%.

[0063]

[0064] 1 H NMR (400MHz, DMSO-d 6 )δ12.09(s,1H),8.13(d,J=7.4Hz,1H),8.00(d,J=7.2Hz,1H),7.67(t,J=7.2Hz,1H),7.59(d, J=8.2Hz, 1H), 7.36(t, J=8.2Hz, 1H), 7.33(d, J=8.2Hz, 2H), 7.12(d, J=8.2Hz, 2H), 2.27(s, 3H) ;

[0065] 13 C NMR (100MHz, DMSO-d 6 )δ174.8, 142.8, 140.1, 136.8, 132.4, 132.2, 130.5, 127.4, 125.8, 124.5, 124.3, 118.9, 110.9, 21.1.

Embodiment 2

[0067] Compound 2, 3-(phenylselanyl)quinolin-4(1H)-one, yield 95%.

[0068]

[0069] 1 H NMR (400MHz, DMSO-d 6 )δ12.20(s,1H),8.20-8.14(m,2H),7.72-7.69(m,1H),7.68-7.61(m,1H),7.41(t,J=7.2Hz,3H),7.29 -7.20(m,3H);

[0070] 13 C NMR (100MHz, DMSO-d 6 )δ175.0, 144.3, 140.2, 132.5, 131.9 131.0, 129.7, 126.9, 125.8, 124.2, 124.4, 119.0, 109.7.

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Abstract

The invention discloses an electrochemical synthesis method of a 3-aryl seleno quinolinone compound. According to the method, a solution containing a quinolinone compound, diaryldiselenide and potassium iodide is used as an electrolytic solution, a glassy carbon anode and a glassy carbon cathode are placed in the electrolytic solution, direct current is introduced, and an electrochemical reactionis carried out to obtain the 3-aryl seleno quinolinone compound. The method has the advantages of mild reaction conditions, simple operation, environmental protection, easily available raw materials,excellent compatibility of substrate functional groups, high reaction yield and the like.

Description

technical field [0001] The invention discloses an electrochemical synthesis method of a 3-aryl selenyl quinolinone compound, and particularly relates to a method for catalyzing quinolinone and diaryl diquinolone with potassium iodide under the condition of no external oxidant and electrolyte under the action of direct current. The invention discloses a method for synthesizing 3-aryl selenyl quinolinone derivatives by electrochemical reaction of selenide, which belongs to the technical field of organic intermediate synthesis. Background technique [0002] 3-Arylselenoquinolinone compounds have a wide range of biological activities and play an important role in the field of drug research and development. Diaryl diselenide is a very easy-to-obtain raw material. Using diaryl diselenide as a selenization reagent, the C-H / C-Se oxidative dehydrogenation coupling of quinolinone and diaryl diselenide The joint reaction is one of the ideal methods for the preparation of 3-aryl seleny...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C25B3/10C25B3/29
Inventor 何卫民彭莎
Owner HUNAN UNIV OF SCI & ENG
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