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

Method for synthesizing 3-cyano-substituted imidazo [1, 5-a] quinoline compound

A technology of cyano substitution and imidazolo, applied in the field of organic synthesis methodology, can solve the problem that there are no relevant reports on aromatic cyanide compounds

Active Publication Date: 2020-11-10
UNIV OF SCI & TECH OF CHINA
View PDF7 Cites 4 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[7]However, for multi-component reactions, there is still no relevant report on the construction of aromatic cyanides

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 3-cyano-substituted imidazo [1, 5-a] quinoline compound
  • Method for synthesizing 3-cyano-substituted imidazo [1, 5-a] quinoline compound
  • Method for synthesizing 3-cyano-substituted imidazo [1, 5-a] quinoline compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0079] Preparation of 1-phenyl-imidazo[1,5-a]quinoline-3-carbonitrile

[0080]

[0081] Put 2-methylquinoline (0.3mmol, 43.0mg), benzylamine (0.9mmol, 96.4mg), trimethylsilyl cyanide (0.9mmol, 89.3mg) and ammonium iodide in a 10mL non-separated electrolytic cell (0.3 mmol, 43.5 mg) and N,N-dimethylacetamide (3.0 mL), the platinum plate electrode was used as both anode and cathode, and reacted under electric stirring (I=10mA) at 90°C. After the reaction was completed (TLC tracking detection), the obtained residue was spin-dried and used ethyl acetate / petroleum ether system as the eluent to pass through the chromatographic column to obtain the product 1-phenyl-imidazo[1,5-a]quinoline-3 -Formonitrile, 97% yield.

[0082] The cyanation product is analyzed by a nuclear magnetic resonance spectrometer, and the results can be found in Figure 1~2 . figure 1 For the cyanation product that the embodiment of the present invention 1 provides 1 H NMR ( 1 H-NMR) spectrogram; figu...

Embodiment 2

[0085] Preparation of 1-(4-methylphenyl)-imidazo[1,5-a]quinoline-3-carbonitrile

[0086]

[0087] Put 2-methylquinoline (0.3mmol, 43.0mg), 4-methylbenzylamine (0.9mmol, 109.1mg), trimethylsilyl cyanide (0.9mmol, 89.3mg) in a 10mL electrolytic cell without separation , ammonium iodide (0.3mmol, 43.5mg) and N,N-dimethylacetamide (3.0mL), the platinum plate electrode was used as both anode and cathode, and reacted under electric stirring (I=10mA) at 90°C. After the reaction was completed (TLC tracking detection), the obtained residue was spin-dried and used ethyl acetate / petroleum ether system as the eluent to pass through the chromatographic column to obtain the product 1-(4-methylphenyl)-imidazo[1,5- a] Quinoline-3-carbonitrile in 94% yield.

[0088] The cyanation product is analyzed by a nuclear magnetic resonance spectrometer, and the results can be found in Figure 3-4 . image 3 For the cyanation product that the embodiment of the present invention 2 provides 1 H NMR...

Embodiment 3

[0091] Preparation of 1-(4-chlorophenyl)imidazo[1,5-a]quinoline-3-carbonitrile

[0092]

[0093] 2-Methylquinoline (0.3mmol, 43.0mg), 4-chlorobenzylamine (0.9mmol, 127.4mg), trimethylsilyl cyanide (0.9mmol, 89.3mg), Ammonium iodide (0.3mmol, 43.5mg) and N,N-dimethylacetamide (3.0mL) were reacted at 90°C with electric stirring (I=10mA) using a platinum sheet electrode as both anode and cathode. After the reaction was completed (TLC tracking detection), the obtained residue was spin-dried and used ethyl acetate / petroleum ether system as an eluent to pass through the chromatographic column to obtain the product 1-(4-chlorophenyl)imidazo[1,5-a] Quinoline-3-carbonitrile, 79% yield.

[0094] The cyanation product is analyzed by a nuclear magnetic resonance spectrometer, and the results can be found in Figure 5-6 . Figure 5 For the cyanation product that the embodiment of the present invention 3 provides 1 H NMR ( 1 H-NMR) spectrogram; Figure 6 For the cyanation product t...

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 relates to a method for synthesizing a 3-cyano-substituted imidazo [1, 5a] quinoline compound. Particularly, the invention provides a method for constructing a 3-cyano-substituted imidazo [1, 5a] quinoline compound by using an electrocatalytic three-component reaction, and the method comprises the following steps: 1) respectively adding an electrolyte, unsubstituted or substituted 2-methylquinoline, substituted fatty amine, a cyano source and a solvent into a non-separated electrolytic cell, installing an electrode in the electrolytic cell, and performing electrifying and stirring to react; 2) separating and purifying the solution after the reaction to obtain the 3-cyano-substituted imidazo [1, 5a] quinoline compound.

Description

technical field [0001] The invention belongs to the field of organic synthesis methodology, in particular to a method for synthesizing 3-cyano-substituted imidazo[1,5-a]quinoline compounds. Background technique [0002] Aryl cyanide compounds are widely found in natural products, drug molecules, pesticides and dyes. [1] In addition, the cyano group is a very important class of synthetic intermediates in organic chemistry because it can be converted into a variety of functional groups. [2] Therefore, the synthesis of aryl cyanide compounds has always been the research focus of organic chemists. [3] Especially cyano-functionalized imidazo[1,5-a] nitrogen-containing heterocycles, [4] It is an important aromatic cyanide compound with a biologically active framework, and its research is relatively less than other aryl cyanide compounds. [0003] In recent years, some metal-catalyzed cyano-functionalized imidazo[1,5-a] nitrogen-containing heterocycles have been developed at hom...

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): C25B3/00
CPCC25B3/00
Inventor 汪志勇钱鹏查正根
Owner UNIV OF SCI & TECH OF CHINA
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