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

Synthesis method of 1, 2, 3-triazole quinoxalinone derivative

A technology of triazole quinoxalinone and synthesis method, which is applied in the direction of organic chemistry and the like, can solve the problems of many steps, narrow range of substrate universality, low yield and the like, and achieves the effect of strong biological activity

Active Publication Date: 2022-03-18
CHANGZHOU UNIV
View PDF3 Cites 0 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, there are few reports on the synthesis of these structures, and the reported traditional methods have limitations such as many steps, narrow substrate universality, and low yields.

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
  • Synthesis method of 1, 2, 3-triazole quinoxalinone derivative
  • Synthesis method of 1, 2, 3-triazole quinoxalinone derivative
  • Synthesis method of 1, 2, 3-triazole quinoxalinone derivative

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0022] Under blue light irradiation, 1-methylquinoxalinone (0.5mmol), diazotrivalent iodine reagent 1 (0.75mmol), three (2,2'-bipyridyl) ruthenium dichloride (5%mmol) and 1,1 dichloroethane (2 mL) was added into a 15 mL test tube, reacted at room temperature for 10 hours, and separated by silica gel column chromatography to obtain the target compound 3a in a yield of 66%. 1 H NMR (300MHz, CDCl 3 )δ8.61(dd, J=8.7,1.7Hz,1H),7.68-7.62(m,1H),7.49-7.44(m,2H),4.56(q,J=7.1Hz,2H),3.77(s ,3H),1.49(t,J=7.1Hz,3H).

Embodiment 2

[0024] Under blue light irradiation, 7-fluoro-1-methylquinoxalinone (0.5mmol), diazotrivalent iodine reagent 1 (0.75mmol), tris(2,2'-bipyridyl)ruthenium dichloride (5 % mmol) and 1,1-dichloroethane (2 mL) were added to a 15 mL test tube, reacted at room temperature for 12 hours, and separated by silica gel column chromatography to obtain the target compound 3b with a yield of 75%. 1 H NMR (500MHz, CDCl 3 )δ8.33(dd,J=7.9,2.8Hz,1H),7.49-7.46(m,1H),7.42-7.40(m,1H),4.57(q,J=7.1Hz,2H),3.78(s ,3H).

Embodiment 3

[0026] Under blue light irradiation, 7-chloro-1-methylquinoxalinone (0.5mmol), diazo trivalent iodine reagent 1 (0.75mmol), three (2,2'-bipyridyl) ruthenium dichloride (5 % mmol) and 1,1-dichloroethane (2 mL) were added to a 15 mL test tube, reacted at room temperature for 12 hours, and separated by silica gel column chromatography to obtain the target compound 3c with a yield of 80%. 1 H NMR (300MHz, CDCl 3 )δ8.53(d, J=2.0Hz, 1H), 7.53(dd, J=8.9, 2.2Hz, 1H), 7.34(d, J=9.0Hz, 1H), 4.48(q, J=7.1Hz, 2H), 3.67(s, 3H), 1.41(t, J=7.1Hz, 3H).

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 belongs to the technical field of organic synthesis and medicines, and particularly relates to a synthesis method of a 1, 2, 3-triazole quinoxalinone derivative. Under ruthenium catalysis, a quinoxaline ketone derivative and a diazonium trivalent iodine reagent are used as raw materials, under blue light irradiation, stirring is performed in a solvent, and a reaction is performed at room temperature to obtain the 1, 2, 3-triazole quinoxaline ketone derivative. By using the method provided by the invention, the 1, 2, 3-triazole quinoxalinone derivative can be obtained by reacting for 10-15 hours at room temperature, and the yield is 66-82%. According to the reaction, the 1, 2, 3-triazole quinoxalinone derivative is simply, conveniently and rapidly synthesized by adopting simple and easily available raw materials under the conditions of ruthenium catalysis and blue light irradiation, and a novel simple, efficient and mild synthesis method is provided for synthesizing the 1, 2, 3-triazole quinoxalinone derivative.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis and medicine, in particular to a synthesis method of 1,2,3-triazolequinoxalinone derivatives. Background technique [0002] Heterocyclic compounds are the largest class of organic compounds, which are commonly found in drug molecules. Heteropolycyclic compounds, especially 1,2,3-triazolequinoxalinone derivatives and their similar tricyclic systems, have shown strong biological activities, such as G-protein coupled hydrochloric acid receptor 109A antagonists, diazepam receptor inhibitors, etc. [(a) Sharma, S.; Sharma, P.K.; Kumar, N.; Dudhe, R. Pharma. Chemica., 2010, 2, 253. (b) Khalilullah, H.; Ahsan, M.J.; Hedaitullah, M.; Khan, S.; Ahmed, B. Mini-Rev. Med. Chem., 2012, 12, 789]. However, there are few reports on the synthesis of these structures, and the reported traditional methods have limitations such as many steps, narrow substrate universality, and low yields. [0003] At pre...

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
IPC IPC(8): C07D487/04
CPCC07D487/04
Inventor 李剑赵文艳朱娅南邓长江董春萍陈俊名马晓明
Owner CHANGZHOU UNIV
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