Looking for breakthrough ideas for innovation challenges? Try Patsnap Eureka!

Method for synthesizing C-3 alkyl substituted quinoxalinone by nickel catalysis under an electrochemical condition

A quinoxalinone and synthesis method technology, applied in the direction of electrolysis components, electrodes, electrolysis process, etc., can solve the problems of low yield, high reaction temperature, environmental pollution, etc., and achieve the goal of reducing energy consumption, simple operation, and convenient operation Effect

Active Publication Date: 2020-04-10
BEIJING UNIV OF TECH
View PDF5 Cites 5 Cited by
  • 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

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
View more

Image

Smart Image Click on the blue labels to locate them in the text.
Viewing Examples
Smart Image
  • Method for synthesizing C-3 alkyl substituted quinoxalinone by nickel catalysis under an electrochemical condition
  • Method for synthesizing C-3 alkyl substituted quinoxalinone by nickel catalysis under an electrochemical condition
  • Method for synthesizing C-3 alkyl substituted quinoxalinone by nickel catalysis under an electrochemical condition

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0023] Embodiment 1: Electrochemical method synthesizes 3-cyclohexyl quinoline-2 (1H)-ketone

[0024] In a 10ml single-chamber electrolytic cell, add raw material 2-quinoxalinone (0.3mmol), redox active ester (0.6mmol), LiClO 4 (1.0mmol), NiCl 2 .6H 2 O (0.6 mmol), 4,4'-di-tert-butyl-2,2'-bipyridine (0.6 mmol). The apparatus was sealed and argon was injected into the tube (three times). Then, under an argon atmosphere, N,N-dimethylacetamide (DMA, 4.0 mL) and triethylamine (0.25 mL) were added via a syringe and closed with a rubber stopper, and an argon-filled balloon was inserted into the bottle. The mixture was first reacted under magnetic stirring at 60°C for 30 minutes, and then 2 Electrolyze for 3 hours at current density. After the reaction was complete, the mixture was quenched with water and extracted with ethyl acetate (3 x 10ml). The organic phase was concentrated on a rotary evaporator. The desired product was purified by column chromatography in a silica gel ...

Embodiment 2

[0027] Embodiment 2: Electrochemical synthesis of 3-(4-isopropylcyclohexyl)quinoxalin-2(1H)-one

[0028] In a 10ml single-chamber electrolytic cell, add raw material 2-quinoxalinone (0.3mmol), redox active ester (0.6mmol), LiClO 4 (1.0mmol), NiCl 2 .6H 2 O (0.6 mmol), 4,4'-di-tert-butyl-2,2'-bipyridine (0.6 mmol). The apparatus was sealed and argon was injected into the tube (three times). Then, under an argon atmosphere, N,N-dimethylacetamide (DMA, 4.0 mL) and triethylamine (0.25 mL) were added via a syringe and closed with a rubber stopper, and an argon-filled balloon was inserted into the bottle. The mixture was first reacted under magnetic stirring at 60°C for 30 minutes, and then 2Electrolyze for 3 hours at current density. After the reaction was complete, the mixture was quenched with water and extracted with ethyl acetate (3 x 10ml). The organic phase was concentrated on a rotary evaporator. The desired product was purified by column chromatography on silica gel ...

Embodiment 3

[0031] Example 3: Electrochemical synthesis of 3-(4,4-difluorocyclohexyl)quinoxalin-2(1H)-one

[0032] In a 10ml single-chamber electrolytic cell, add raw material 2-quinoxalinone (0.3mmol), redox active ester (0.6mmol), LiClO 4 (1.0mmol), NiCl 2 .6H 2 O (0.6 mmol), 4,4'-di-tert-butyl-2,2'-bipyridine (0.6 mmol). The apparatus was sealed and argon was injected into the tube (three times). Then, under an argon atmosphere, N,N-dimethylacetamide (DMA, 4.0 mL) and triethylamine (0.25 mL) were added via a syringe and closed with a rubber stopper, and an argon-filled balloon was inserted into the bottle. The mixture was first reacted under magnetic stirring at 60°C for 30 minutes, and then 2 Electrolyze for 3 hours at current density. After the reaction was complete, the mixture was quenched with water and extracted with ethyl acetate (3 x 10ml). The organic phase was concentrated on a rotary evaporator. The desired product was purified by column chromatography on silica gel (...

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

PUM

No PUM Login to View More

Abstract

The invention discloses a method for synthesizing C-3 alkyl substituted quinoxalinone by nickel catalysis under an electrochemical condition, and belongs to the technical field of preparation of compounds. The method comprises the steps: taking 2-hydroxyquinoxaline and N-hydroxyphthalimide ester as raw materials in a single-compartment electrolytic cell, in an electrolyte solution, taking nickel chloride hexahydrate as a catalyst, 4,4'-di-tert-butyl-2,2'-dipyridine as a ligand, carrying out electrolysis under the condition that lithium perchlorate is used as a supporting electrolyte, carryingout a reaction for 3 h at the reaction temperature of 60 DEG C and with the current density of 8 mA / cm<2>, and thus obtaining the C-3 substituted alkylated quinoxalinone compounds with different structures. The method has the advantages of mild reaction, use of the cheap and easily available nickel metal catalyst, and good functional group compatibility. Besides, the electrochemical method provides a green and effective method for the synthesis of various alkyl substituted quinoxalinone compounds, and is helpful for realizing atom economy, so that the cost is greatly reduced, the operation ismuch simpler, and the industrial production is facilitated.

Description

technical field [0001] The invention relates to a novel synthesis method of an electrochemical C-3 alkylated quinoxalinone using a cheap nickel salt as a catalyst, and belongs to the technical field of compound preparation. Background technique [0002] Quinoxalinones are an important class of heterocyclic compounds, which contain two heteroatoms. Quinolinones are also a very important nitrogen heterocyclic compound. Due to their anticancer, antibacterial, antithrombotic, and protein kinase inhibitory , receptor agonist activity and other biological activities, as well as the activity of some pathogenic microorganisms, they are widely used in medicine, sterilization, weeding, 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 pharmaceuticals. In organic chemistry, quinoxalinones are often used as raw materials for a series of reactions. For example, acylation, pho...

Claims

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

Application Information

Patent Timeline
no application Login to View More
Patent Type & Authority Applications(China)
IPC IPC(8): C25B3/00C25B11/06
CPCC25B3/00C25B11/04
Inventor 徐坤廉菲曾程初
Owner BEIJING UNIV OF TECH
Who we serve
  • R&D Engineer
  • R&D Manager
  • IP Professional
Why Patsnap Eureka
  • Industry Leading Data Capabilities
  • Powerful AI technology
  • Patent DNA Extraction
Social media
Patsnap Eureka Blog
Learn More
PatSnap group products

Browse by: Latest US Patents, China's latest patents, Technical Efficacy Thesaurus, Application Domain, Technology Topic, Popular Technical Reports.

© 2024 PatSnap. All rights reserved.Legal|Privacy policy|Modern Slavery Act Transparency Statement|Sitemap|About US| Contact US: help@patsnap.com