A kind of synthetic method of quinoxalinone compound

A quinoxalinone and a synthesis method technology are applied in the field of new quinoxalinone compounds and their preparation, and can solve the problems of reagent toxicity, inability to meet production requirements in the fields of medicine and chemical synthesis, single type of reaction substrate, and the like, Achieve the effect of green post-treatment, wide range of system application and strong reaction specificity

Active Publication Date: 2022-08-09
NINGXIA UNIVERSITY
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  • Claims
  • Application Information

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Problems solved by technology

[0003] Although the preparation methods of various types of quinoxalinone compounds have been disclosed in the prior art, these methods still cannot meet the production requirements in the fields of medicine and chemical synthesis
These methods still have relatively large limitations, such as the types of reaction substrates that can be catalyzed are relatively single; the reagents used in some reactions are more toxic, etc., and it is necessary to develop new methodology for the synthesis of quinoxalinone compounds

Method used

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  • A kind of synthetic method of quinoxalinone compound
  • A kind of synthetic method of quinoxalinone compound
  • A kind of synthetic method of quinoxalinone compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0017] combine figure 2 ,Be explained. The chloroimine substrate 1 (1 equiv., 0.5 mmol), palladium trifluoroacetate (0.2 equiv., 0.1 mmol), Na 2 CO 3 (2.0 equiv., 1.0 mmol) in 1,2-dichloroethane (DCE, 5 mL). The reaction solution was placed at 100 o C oil bath, react under argon for 6h. After the completion of the reaction was detected by TLC, the reaction solution was washed with saturated NH 4 Quenched with aqueous Cl solution, extracted with ethyl acetate, anhydrous Na 2 SO 4 After drying, the solvent was removed and the expected product 2 was obtained by column chromatography.

Embodiment 2

[0019] combine image 3 ,Be explained. The chloroimine substrate 3 (1 equiv., 0.5 mmol), palladium trifluoroacetate (0.2 equiv., 0.1 mmol), Na 2 CO 3 (2.0 equiv., 1.0 mmol)) in 1,2-dichloroethane (DCE, 5 mL). The reaction solution was placed at 100 o In the C oil bath, the reaction was carried out under air condition for 20h. After the completion of the reaction was detected by TLC, the reaction solution was washed with saturated NH 4 Quenched with aqueous Cl solution, extracted with ethyl acetate, anhydrous Na 2 SO 4 After drying, the solvent was removed and the expected product 4 was obtained by column chromatography.

[0020] After characterization, the spectral information of some products is analyzed as follows:

[0021]

[0022] 4-Benzyl-3-oxo-3,4-dihydroquinoxaline-2-carboxylate ethyl ester

[0023] butter; 1 H NMR (CDCl 3 , 400 MHz, o ppm): 7.92 (d, J = 8.0 Hz, 1H), 7.52-7.48 (m, 1H), 7.34-7.24 (m, 7H), 5.48 (s, 2H), 4.52 (q, J = 7.2 Hz, 2H), 1.44(t, ...

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Abstract

The present invention is to dissolve the chloroimine substrate in the addition of Na 2 CO 3 In the dichloroethane solution, under the catalysis of palladium trifluoroacetate, the reaction is carried out in an oil bath for 6-20 h. According to the different functional groups carried by the chloroimine substrate, the reaction atmosphere under the oil bath reaction conditions is different: Imine substrate with CO attached 2 When the Et group is used, the reaction atmosphere is argon, and when the chloroimine substrate is attached to an aryl group, the reaction atmosphere is air. After the completion of the reaction, through thin layer chromatography (TLC) detection, the reaction solution was saturated NH 4 Quenched with aqueous Cl solution, extracted with ethyl acetate, anhydrous Na 2 SO 4 After drying, the solvent was removed, and the quinoxalinone compounds were obtained by column chromatography.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis, and in particular relates to a novel quinoxalinone compound and a preparation method thereof. Background technique [0002] Quinoxalinone compounds are important nitrogen-containing heterocyclic compounds with important medicinal value and application prospects, and are widely used in chemistry, medicine, materials, agricultural science and other fields. Their synthesis has increasingly attracted the attention of organic chemists. Interest, a variety of new methods for the synthesis of quinoxalinone products have been developed, such as figure 1 . [0003] Although the preparation methods of various types of quinoxalinone compounds have been disclosed in the prior art, these methods still cannot meet the production requirements in the fields of medicine and chemical synthesis. These methods still have major limitations, such as the type of reaction substrates that can be catalyzed is ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D241/44
CPCC07D241/44Y02P20/584
Inventor 李典军杨金会李文爽樊煦
Owner NINGXIA UNIVERSITY
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