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

A 3-iminoimidazo[1,2-a]pyridine compound

A technology of iminoimidazole and compound, which is applied in the field of synthesis of 3-iminoimidazo[1,2-a]pyridine compounds, achieving the effects of atom economy, simple reaction operation and good chemoselectivity

Active Publication Date: 2021-06-04
EAST CHINA UNIV OF TECH
View PDF2 Cites 0 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, so far, the synthesis of 3-iminoimidazo[1,2-a] from N-arylglycine esters and imidazo[1,2-a]pyridine compounds using green, clean and sustainable visible light Pyridine compounds have no literature and patent reports

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
  • A 3-iminoimidazo[1,2-a]pyridine compound
  • A 3-iminoimidazo[1,2-a]pyridine compound
  • A 3-iminoimidazo[1,2-a]pyridine compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0021] N-4-tolylglycine ethyl ester (0.15mmol), 2-phenylimidazo[1,2-a]pyridine (0.18mmol), eosin Y (0.015mmol) and citric acid monohydrate (0.18mmol) Add to a dry reaction tube with a magnetic stirrer. Then, ethanol (2 mL) was added to the test tube as a solvent, and the reaction mixture was placed in an air atmosphere at room temperature and irradiated with 18W LED blue light for 18 hours. After the reaction was detected by TLC, the solvent was distilled off with a rotary evaporator under reduced pressure, and the residue was separated and purified by column chromatography to obtain a pure yellow solid 3aa with a yield of 73%. The structural characterization data of the 3aa compound are as follows:

[0022]

[0023] Light yellow solid; mp 164.4-168.8℃; 1 H NMR (500MHz, CDCl 3 ): δ9.79(d, J=7.0Hz, 1H), 7.79(d, J=8.9Hz, 1H), 7.61(dd, J=6.6Hz, J=3.0Hz, 2H), 7.50-7.46(m ,1H),7.40(dd,J=5.0Hz,J=1.7Hz,3H),7.12(d,J=8.0Hz,2H),7.03(td,J=6.9Hz,J=1.2Hz,1H), 6.84(d, J=8.2Hz, 2H), ...

Embodiment 2

[0025] N-3-tolylglycine ethyl ester (0.15mmol), 2-phenylimidazo[1,2-a]pyridine (0.18mmol), eosin Y (0.015mmol) and citric acid monohydrate (0.18mmol) Add to a dry reaction tube with a magnetic stirrer. Then, ethanol (2 mL) was added to the test tube as a solvent, and the reaction mixture was placed in an air atmosphere at room temperature and irradiated with 18W LED blue light for 18 hours. After the reaction was detected by TLC, the solvent was distilled off with a rotary evaporator under reduced pressure, and the residue was separated and purified by column chromatography to obtain a pure light yellow solid 3ab with a yield of 53%. The structural characterization data of the 3ab compound are as follows:

[0026]

[0027] Light yellow solid; mp 161.4-164.3℃; 1 H NMR (500MHz, CDCl 3 ): δ9.81(d, J=7.0Hz, 1H), 7.80(d, J=9.0Hz, 1H), 7.63(dd, J=7.5Hz, J=4.0Hz, 2H), 7.51-7.47(m ,1H),7.43-7.40(m,3H),7.22(t,J=7.5Hz,1H),7.04(t,J=7.0Hz,1H),6.96(d,J=7.5Hz,1H),6.80 (s,1H),6.75(d,...

Embodiment 3

[0029]N-phenylglycine ethyl ester (0.15mmol), 2-phenylimidazo[1,2-a]pyridine (0.18mmol), eosin Y (0.015mmol) and citric acid monohydrate (0.18mmol) were added to In a dry reaction tube with a magnetic stirrer. Then, ethanol (2 mL) was added to the test tube as a solvent, and the reaction mixture was placed in an air atmosphere at room temperature and irradiated with 18W LED blue light for 17 hours. After the reaction was detected by TLC, the solvent was distilled off with a rotary evaporator under reduced pressure, and the residue was separated and purified by column chromatography to obtain a pure light yellow solid 3ac with a yield of 73%. The structural characterization data of the 3ac compound are as follows:

[0030]

[0031] Light yellow solid; mp 162.9-164.6℃; 1 H NMR (500MHz, CDCl 3 ):δ9.80(d,J=7.0Hz,1H),7.80(d,J=9.0Hz,1H),7.63-7.60(m,2H),7.51-7.47(m,1H),7.42-7.39( m,3H),7.34-7.30(m,2H),7.13(t,J=7.5Hz,1H),7.04(td,J=7.0Hz,J=1.0Hz,1H),6.93(dd,J=8.5 Hz, J=1.0Hz, 2...

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 visible light-catalyzed oxidative cross-coupling reaction of N-aryl glycine ester and imidazo[1,2-a]pyridine compound to prepare 3-imino imidazo[1,2-a]pyridine compound. In the method of the present invention, eosin Y is a photosensitizer, citric acid is an additive, and N-aryl glycine ester and imidazo[1,2-a]pyridine compound are directly dehydrogenated after being irradiated with visible light at room temperature in an organic solvent Cross-coupling yields 3‑iminoimidazo[1,2‑a]pyridine compounds. The method of the present invention uses eosin Y as a photosensitizer, citric acid monohydrate as an additive, and ethanol as a solvent, and utilizes visible light catalysis to effectively prepare a 3-iminoimidazo[1,2-a]pyridine in an air atmosphere at room temperature compound. The method of the invention has the advantages of simple and convenient operation, mild reaction conditions, good selectivity and atom economy.

Description

technical field [0001] The invention belongs to the field of organic chemistry, and relates to the synthesis of imidazo[1,2-a]pyridine compounds, in particular to a synthesis method of 3-imino imidazo[1,2-a]pyridine compounds. Background technique [0002] Imidazo[1,2-a]pyridine is an important class of aromatic nitrogen-containing heterocyclic compounds, which have a very wide range of applications in the fields of medicine, pesticides and materials science. These compounds have attracted great attention from chemists because of their specific physiological and chemical activities. Many imidazo[1,2-a]pyridine compounds have antibacterial, antiviral, and anxiolytic activities, and can be used as prescription drugs for the treatment of tumors, hypertension, diabetes, and psychosis, etc., and can also be used as backup drugs for the treatment of leukemia, hepatitis, etc. . For example, the structure of imidazo[1,2-a]pyridine substituted at the C3 position exists in some impo...

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 Patents(China)
IPC IPC(8): C07D471/04
Inventor 祝志强郭栋肖利金
Owner EAST CHINA 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