Photocatalytic preparation method of 3-aminoquinoxaline-2(1H)-ketone compound

A ketone compound and photocatalytic technology, applied in the direction of organic chemistry, can solve the problems of difficult to deal with metal ion residues, poor compatibility of reactive functional groups, high reaction temperature and other problems, and achieve the goal of reducing metal pollution, good compatibility and clean energy Effect

Active Publication Date: 2019-01-08
QUFU NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Although this method is more effective, there are still some shortcomings in this type of reaction. For example, as shown in the following reaction formula, route (a) needs to add 2 equivalents of potassium permanganate metal reagent or 1.2 equivalents of AgPy2MnO4 as the oxidant, and the reaction Poor functional group compatibility, serious environmental pollution (Tetrahedron 2008, 64, 696−707); route (b) uses transition metal copper salt to catalyze the reaction, and the reaction requires high reaction temperature, and the problem of metal ion residue is difficult to deal with (Org

Method used

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  • Photocatalytic preparation method of 3-aminoquinoxaline-2(1H)-ketone compound
  • Photocatalytic preparation method of 3-aminoquinoxaline-2(1H)-ketone compound
  • Photocatalytic preparation method of 3-aminoquinoxaline-2(1H)-ketone compound

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0033]

[0034] At room temperature, in a 15mL reaction tube, sequentially add quinoxalin-2(1H)-one 1a (0.2mmol), morpholine (0.4mmol), water-soluble eosin (0.002mmol), and tetrahydrofuran 2mL, mix well, and then Under the irradiation of 3W watt blue LED lamp, the reaction was stirred for 12h. After the reaction was detected by TLC, 2 mL of water was added, followed by extraction with ethyl acetate for 3 times, the extracts were combined, dried over anhydrous sodium sulfate, and then concentrated under vacuum (0.08Mpa) to nothing. Solvent, to obtain the crude product, then wash with the mixed eluent of sherwood oil and ethyl acetate with a volume ratio of 3:1, silica gel column flash column chromatography, obtain the present embodiment 3-aminoquinoxaline-2 (1H) - The ketone product 3aa is 40.2 mg of white solid, and the yield is 82%.

[0035] The obtained product nuclear magnetic spectrum data are: 1 H NMR (CDCl 3 , 500 MHz, ppm): δ 7.57 (dd, J =1.3Hz, 7.7Hz, 1H), 7....

Embodiment 2

[0038]

[0039] At room temperature, in a 15mL reaction tube, sequentially add quinoxalin-2(1H)-one 1b (0.2mmol), morpholine (0.4mmol), water-soluble eosin (0.002mmol), and tetrahydrofuran 2mL, mix well, and then Under the irradiation of 3W (watt) blue LED lamp, the reaction was stirred for 18h. After the reaction was detected by TLC, 2 mL of water was added, followed by extraction with ethyl acetate for 3 times, the extracts were combined, dried over anhydrous sodium sulfate, and then concentrated under vacuum (0.08Mpa) to nothing. Solvent, to obtain the crude product, then wash with the mixed eluent of sherwood oil and ethyl acetate with a volume ratio of 3:1, silica gel column flash column chromatography, obtain the present embodiment 3-aminoquinoxaline-2 (1H) - The ketone product 3ba is 39.4 mg of white solid, with a yield of 67%.

[0040] The obtained product nuclear magnetic spectrum data are: 1 H NMR (CDCl 3 , 500 MHz, ppm): δ 7.56 (dd, J =1.4Hz,7.8Hz, 1H), 7....

Embodiment 3

[0043]

[0044] At room temperature, in a 15mL reaction tube, add quinoxalin-2(1H)-one 1c (0.2mmol), morpholine (0.4mmol), rose bengal (0.002mmol), and tetrahydrofuran 2mL in sequence, mix well, and then Under the irradiation of 3W blue LED light, the reaction was stirred for 12h. After the reaction was detected by TLC, 2 mL of water was added, followed by extraction with ethyl acetate for 3 times, the extracts were combined, dried over anhydrous sodium sulfate, and then concentrated under vacuum (0.08Mpa) to nothing. Solvent, to obtain the crude product, then wash with the mixed eluent of sherwood oil and ethyl acetate with a volume ratio of 3:1, silica gel column flash column chromatography, obtain the present embodiment 3-aminoquinoxaline-2 (1H) - The ketone product 3ca is 45.6 mg of white solid, with a yield of 71%.

[0045] The NMR data of the obtained product are . 1 H NMR (CDCl 3 , 500 MHz, ppm): δ 7.56 (dd, J =1.4 Hz, 7.9 Hz, 1H), 7.30 (t, J = 7.1 Hz, 2H), ...

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Abstract

The invention relates to a photocatalytic preparation method of a 3-aminoquinoxaline-2(1H)-ketone compound, in particular to a method for preparing a 3-aminoquinoxaline-2(1H)-ketone compound based onphotocatalysis. The reaction formula of the preparation method is as shown in the description, wherein R1 is a hydrogen atom or randomly substituted fluorine, chlorine, bromine, iodine, nitryl, estergroup, cyanogroup, alkoxy, aryl, heteroaryl and 1-12 carbon alkyl; R2 is randomly substituted 1-12 carbon alkyl, allyl, propargyl, aryl or hydrogen atom; R3 is randomly substituted 1-12 carbon alkyl,naphthenic base, benzyl, allyl and propargyl; and R4 is randomly substituted 1-12 carbon alkyl, allyl, benzyl, propargyl or hydrogen atom. The photocatalytic preparation method of the 3-aminoquinoxaline-2(1H)-ketone compound adopts a visible light catalytic technology, is mild in reaction condition, simple to operate, clean in energy source and safe and reliable in process; and the use of a metalreagent and a strong oxidant is avoided, and a strong application value is achieved.

Description

technical field [0001] The invention belongs to the field of organic synthetic chemistry, in particular to a photocatalytic preparation method of a 3-aminoquinoxalin-2(1H)-one compound Background technique [0002] 3-Aminoquinoxaline-2(1H)-one compounds have a wide range of applications in the fields of organic synthesis and medicinal chemistry. Its skeleton derivatives widely exist in a variety of biologically active drug molecules, and they have significant biological activities such as anti-tumor, anti-cancer, antibacterial, hypotensive, and anti-diabetic. In recent years, various 3-aminoquinoxaline-2 (1H)-ketone compounds have also been developed as clinical therapeutic drugs, as shown in the following structural formula, compound A is used as a calcium ion channel blocker; compound B Used as an aldose reductase reductase inhibitor; Compound C is a PAS kinase regulator; Compound D is a histamine-4 receptor antagonist (WO 2009045382A1; Chem. Abstr. 2009,150, 398369; Eur...

Claims

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Application Information

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IPC IPC(8): C07D241/44C07D401/04
CPCC07D241/44C07D401/04
Inventor 魏伟王雷雷吕玉芬王桦
Owner QUFU NORMAL UNIV
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