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A method for electrochemically synthesizing 3-alkylselenyl-4-aminocoumarin compounds

A technology of aminocoumarin and synthesis method, which is applied in the field of electrochemically synthesizing 3-alkylselenyl-4-aminocoumarin compounds, can solve the problem of high cost, serious environmental pollution, and the inability to use 3-alkylselenyl-4 - Issues such as the synthesis of anilinocoumarin compounds, achieving the effects of reducing recovery steps, high reaction selectivity, and facilitating large-scale production

Active Publication Date: 2022-03-01
HUNAN UNIV OF SCI & ENG
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

This method not only has high cost and serious environmental pollution, but also cannot be used for the synthesis of 3-alkylselenyl-4-anilinocoumarin compounds

Method used

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  • A method for electrochemically synthesizing 3-alkylselenyl-4-aminocoumarin compounds
  • A method for electrochemically synthesizing 3-alkylselenyl-4-aminocoumarin compounds
  • A method for electrochemically synthesizing 3-alkylselenyl-4-aminocoumarin compounds

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1～3

[0053] The following examples 1 to 3 are all reacted according to the following reaction equation, mainly to investigate the yield situation of different substrates reacting under optimal conditions:

[0054]

[0055] The specific operation steps are: in a 25mL three-neck round bottom flask, add 4-anilinocoumarin (0.6mmol), dialkyl diselenide (0.3mmol), sodium bromide (0.06mmol), DMF (6mL) successively , 10mm × 10mm × 3mm foam electrode as the anode, 10mm × 10mm × 3mm graphite sheet electrode as the cathode. The resulting mixture was stirred and reacted under a 14 mA direct current at room temperature. The progress of the reaction was followed by thin-layer chromatography, and the reaction time was 4 hours. After the reaction was completed, 6ml of water was added and the product was precipitated, filtered and dried to obtain the pure product.

Embodiment 1

[0057] Compound 1, yield 96%, 3-(methylselanyl)-4-(phenylamino)-2H-chromen-2-one

[0058]

[0059] 1 H NMR (400MHz, CDCl 3 )δ7.81(s,1H),7.44-7.40(m,1H),7.34-7.32(m,3H),7.22-7.17(m,2H),7.05(d,J=8.0Hz,2H),6.90 (t,J=8.4Hz,1H),2.25(s,3H);

[0060] 13 C NMR (100MHz, CDCl 3 )δ160.9, 155.2, 153.9, 141.6, 132.1, 129.7, 126.5, 125.5, 123.2, 123.0, 117.5, 113.8, 99.1, 8.4;

Embodiment 2

[0062] Compound 2, yield 94%, 3-(benzylselanyl)-4-(phenylamino)-2H-chromen-2-one

[0063]

[0064] 1 H NMR (400MHz, CDCl 3 )δ7.54(s,1H),7.34-7.31(m,1H),7.27-7.23(m,1H),7.16(s,2H),7.12-7.08(m,3H),7.04-7.01(m, 3H),6.97-6.91(m,1H),6.84-6.77(m,1H),6.62(m,2H),4.04(s,2H);

[0065] 13 C NMR (100MHz, CDCl 3 )δ161.4, 156.5, 154.1, 141.1, 139.0, 132.2, 129.4, 128.9, 128.7, 127.1, 126.7, 125.7, 124.0, 123.0, 117.7, 113.6, 96.5, 31.1;

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Abstract

The invention discloses a method for electrochemically synthesizing 3-alkylselenyl-4-aminocoumarin compounds. The method is to use the solution containing 4-anilinocoumarin compound, dialkyl diselenide and bromine salt as the electrolyte, place a nickel anode and a graphite rod cathode in the electrolyte, feed in a direct current, and carry out electrolysis. 3-Alkylselenyl-4-anilinocoumarin compound can be obtained through chemical reaction; the method has the advantages of mild reaction conditions, simple operation, environmental protection, easy availability of raw materials, excellent compatibility of substrate functional groups, and high reaction yield.

Description

technical field [0001] The invention discloses a method for electrochemically synthesizing 3-alkylselenyl-4-aminocoumarin compounds. In particular, it relates to a method of electrochemically reacting 4-anilinocoumarin compound with dialkyl diselenide to synthesize 3-alkaselenyl-4- A method for an anilinocoumarin compound belongs to the technical field of organic intermediate synthesis. Background technique [0002] 3-Alkylselenyl-4-anilinocoumarin compounds have a wide range of biological activities and play an important role in the field of drug research and development. And dialkyl diselenide is a kind of very easy-to-get raw material, utilizes dialkyl diselenide as selenization reagent, is prepared 3-alkane by the C-H bond aromatic selenylation reaction of 4-anilinocoumarin One of the ideal methods for seleno-4-anilinocoumarin derivatives. [0003] In 2018, Yang Daoshan of Qingdao University of Science and Technology and others developed a synthesis method of 3-aryl s...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C25B3/23C25B3/05C25B3/07
Inventor 龚绍峰
Owner HUNAN UNIV OF SCI & ENG
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