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Synthesis method of C-3 alkyl substituted quinoxalinones catalyzed by nickel under electrochemical conditions

The technology of a quinoxalinone and a synthesis method is applied in the field of compound preparation, can solve the problems of high reaction temperature, environmental pollution, low yield and the like, and achieves the effects of simple operation, reduced energy consumption and convenient operation

Active Publication Date: 2021-04-09
BEIJING UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Although there are many studies on the synthesis of C-3 alkyl substituted quinoxalinones, stoichiometric metals and strong oxidants are usually used in the reaction process, and there are problems such as high reaction temperature and low yield. , also caused some pollution to the environment

Method used

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  • Synthesis method of C-3 alkyl substituted quinoxalinones catalyzed by nickel under electrochemical conditions
  • Synthesis method of C-3 alkyl substituted quinoxalinones catalyzed by nickel under electrochemical conditions
  • Synthesis method of C-3 alkyl substituted quinoxalinones catalyzed by nickel under electrochemical conditions

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0023]Example 1: Electrochemical method Synthesis 3-cyclohexylquinoline-2 (1H)-ketone

[0024]In a 10 ml single-chamber electrolytic cell, a raw material 2-quinoxalin (0.3 mmol), redox activated ester (0.6 mmol), Liclo4(1.0mmol), NICL2.6h2O (0.6 mmol), 4,4'-di-tert-butyl-2,2'-bisin (0.6 mmol). The sealing device and the argon injection into the tube (three times). Then, N, N-dimethylacetamide (DMA, 4.0 mL) and triethylamine (0.25 mL) were added via a syringe, and the argon balloon was inserted into the bottle with rubber plug. The mixture was first reacted with a magnetic force of 60 ° C for 30 minutes, then at 8 mA / cm2Electrolysis is 3 hours under current density. After the reaction was completed, the mixture was quenched with water and extracted with ethyl acetate (3 × 10 mL). The organic phase is concentrated on a rotary evaporator. The desired product was separated from the column chromatography eluting elut elut elut elut elut Rativity: 87%.

[0025]

[0026]White solid;1H NMR (400MHz...

Embodiment 2

[0027]Example 2: Electrochemical method synthesis 3- (4-isopropylcyclohexyl) quinoxaline-2 (1H)-ketone

[0028]In a 10 ml single-chamber electrolytic cell, a raw material 2-quinoxalin (0.3 mmol), redox activated ester (0.6 mmol), Liclo4(1.0mmol), NICL2.6h2O (0.6 mmol), 4,4'-di-tert-butyl-2,2'-bisin (0.6 mmol). The sealing device and the argon injection into the tube (three times). Then, N, N-dimethylacetamide (DMA, 4.0 mL) and triethylamine (0.25 mL) were added via a syringe, and the argon balloon was inserted into the bottle with rubber plug. The mixture was first reacted with a magnetic force of 60 ° C for 30 minutes, then at 8 mA / cm2Electrolysis is 3 hours under current density. After the reaction was completed, the mixture was quenched with water and extracted with ethyl acetate (3 × 10 mL). The organic phase is concentrated on a rotary evaporator. The desired product was separated from the column chromatography eluting elut elut elut elut elut elut Rativity: 79%.

[0029]

[0030]Whit...

Embodiment 3

[0031]Example 3: Electrochemical Method Synthesis 3- (4, 4-difluorocyclohexyl) quinoxalin-2 (1H)-ketone

[0032]In a 10 ml single-chamber electrolytic cell, a raw material 2-quinoxalin (0.3 mmol), redox activated ester (0.6 mmol), Liclo4(1.0mmol), NICL2.6h2O (0.6 mmol), 4,4'-di-tert-butyl-2,2'-bisin (0.6 mmol). The sealing device and the argon injection into the tube (three times). Then, N, N-dimethylacetamide (DMA, 4.0 mL) and triethylamine (0.25 mL) were added via a syringe, and the argon balloon was inserted into the bottle with rubber plug. The mixture was first reacted with a magnetic force of 60 ° C for 30 minutes, then at 8 mA / cm2Electrolysis is 3 hours under current density. After the reaction was completed, the mixture was quenched with water and extracted with ethyl acetate (3 × 10 mL). The organic phase is concentrated on a rotary evaporator. The desired product was separated from column chromatography eluting elut elut elut elut elut elut elut Yield: 69%.

[0033]

[0034]White...

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Abstract

The invention discloses a method for synthesizing C-3 alkyl substituted quinoxalinone catalyzed by nickel under electrochemical conditions, and belongs to the technical field of compound preparation. In the method, 2-hydroxyquinoxaline and N-hydroxyphthalimide ester are used as raw materials in a single-chamber electrolytic cell, in an electrolyte, nickel chloride hexahydrate is used as a catalyst, and 4,4' -Di-tert-butyl-2,2'-dipyridine as ligand, electrolyzed under the condition of lithium perchlorate as supporting electrolyte, the reaction temperature is 60℃, and the current density is 8mA / cm 2 , the reaction 3h can obtain C-3 substituted alkylated quinoxalinone compounds with different structures. The method is mild in reaction, uses cheap and readily available nickel metal catalysts, and has good functional group compatibility. In addition, this electrochemical method provides a green and efficient method for the synthesis of various alkyl-substituted quinoxalinone compounds, which contributes to atom economy, greatly reduces the cost and makes the operation simpler. It is more conducive to the realization of industrialized production.

Description

Technical field[0001]The present invention relates to a new method of synthesizing an electrochemical C-3 alkylated quinoxalinone in an inexpensive nickel salt as a catalyst, which belongs to the preparation of compounds.Background technique[0002]Quinoxalinone is an important heterocyclic compound that contains two heteroatoms, quinolinone compounds are also a very important azurocyclic compound, due to its anti-cancer, antibacterial, anti-thrombus, protein kinase inhibition Biological activity such as receptor agonist, as well as the activity of some pathogenic microorganisms, which are widely used in medicine, sterilization, herbicide, plant growth regulation and materials. At the same time, it is widely used in synthetic chemistry and is a key structural unit in materials, natural products and drugs. In organic chemistry, quinoxalinone is often used as a raw material, and a series of reactions can be performed. For example, acylation reactions, phosphating reactions, arylated rea...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D241/44C25B3/05C25B3/09C25B3/07C25B11/075
CPCC25B3/00C25B11/04
Inventor 徐坤廉菲曾程初
Owner BEIJING UNIV OF TECH
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