3-imidazole[1,2-a]pyridine compound

An iminoimidazole, 2-a technology is applied in the field of synthesis of 3-iminoimidazo[1,2-a]pyridine compounds, and achieves the effects of good chemical selectivity, simple operation process and mild reaction conditions

Active Publication Date: 2019-05-10
EAST CHINA UNIV OF TECH
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  • 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

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  • 3-imidazole[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...

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Abstract

The invention discloses a 3-imidazole(1,2-a)pyridine compound which is prepared by an oxidation cross-coupling reaction of a visible-light photocatalytic N-aryl glycine ester and a imidazo(1,2-a)pyridine compound. In the preparation method, eosin Y serves as a photosensitizer, citric acid serves as an additive, and N-aryl glycine ester and imidazo(1,2-a)pyridine compound are directly dehydrogenated and cross-linked to form 3-imidazole(1,2-a)pyridine compound in an organic solvent at room temperature after being irradiated by visible light. Accoding to the preparation method, eosin Y serves asphotosensitizer, citric acid monohydrate serves as additive, ethanol serves as solvent, and the 3-imidazole(1,2-a)pyridine compoundand is effectively prepared by visible light photocatalysis at room temperature. The method has the advantages of simple operation, mild reaction conditions, good selectivity and atomic 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

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D471/04
Inventor 祝志强郭栋肖利金
Owner EAST CHINA UNIV OF TECH
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