Supercharge Your Innovation With Domain-Expert AI Agents!

Method for preparing C-3 oxo substituted imidazole heterocyclic compounds

A technology of compounds and synthetic methods, applied in the fields of organic chemistry, drug combination, antibacterial drugs, etc., to achieve the effects of wide application prospect, high reaction yield and wide application range

Active Publication Date: 2017-07-14
杭州尚合生物医药科技有限公司 +1
View PDF7 Cites 3 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

No effective synthesis of 3-alkoxy or phenoxy substituted imidazole heterocycles has been reported

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 preparing C-3 oxo substituted imidazole heterocyclic compounds
  • Method for preparing C-3 oxo substituted imidazole heterocyclic compounds
  • Method for preparing C-3 oxo substituted imidazole heterocyclic compounds

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0031] Example 1: Preparation of 3-phenoxy-2-phenylimidazo[1,2-a]pyridine

[0032]

[0033] Take a clean reaction bottle, add a small magnet, dry it, add 2-aminopyridine (56.5mg, 0.6mmol), 2-phenoxyacetophenone (42.5mg, 0.2mmol), cuprous iodide (0.01mmol) , 1,2-dichloroethane (1.0 mL), heated at 100° C. under oxygen for 16 hours, and the reaction solution was separated by direct column chromatography to obtain the target product (44.0 mg, yield 77%). White solid, m.p.:145-146℃. 1 H NMR (400MHz, CDCl 3 ): δ=8.07(d, J=7.6Hz, 2H), 7.75(d, J=6.8Hz, 1H), 7.66(d, J=9.2Hz, 1H), 7.41(t, J=7.2Hz, 2H ),7.28-7.35(m,3H),7.20(t,J=7.6Hz,1H),7.12(t,J=7.2Hz,1H),6.97(d,J=8.0Hz,2H),6.77(t ,J=6.8Hz,1H). 13 C NMR (100MHz, CDCl 3 ):δ=156.1,139.9,132.5,131.1,130.2,128.7,127.8,126.5,124.4,123.7,121.6,117.9,115.0,112.3.FTIR(NaCl,cm -1 ):3053.3,2985.8,1647.2,1495.6,1421.5,1390.1,1362.2,1265.3,1201.7,895.0,738.7,706.0.HR-MS(ESI):m / zcalculated for C 19 h 14 N 2 O[M+H]+: 287.1184; found 287.1...

Embodiment 2

[0034] Example 2: Preparation of 3-phenoxy-2-phenylimidazo[1,2-a]pyridine

[0035]

[0036] Take a clean reaction bottle, add a small magnet, dry it, add 2-aminopyridine (56.5mg, 0.6mmol), 2-phenoxyacetophenone (42.5mg, 0.2mmol), cuprous iodide (0.01 mmol) , 1,2-dichloroethane (1.0 mL), heated at 80° C. under oxygen for 16 hours, and the reaction solution was separated by direct column chromatography to obtain the target product (40.0 mg, yield 70%).

Embodiment 3

[0037] Example 3: Preparation of 3-phenoxy-2-phenylimidazo[1,2-a]pyridine

[0038]

[0039] Take a clean reaction bottle, add a small magnet, dry it, add 2-aminopyridine (56.5mg, 0.6mmol), 2-phenoxyacetophenone (42.5mg, 0.2mmol), cuprous iodide (0.01mmol) , 1,2-dichloroethane (1.0 mL), heated at 120° C. under oxygen for 16 hours, and the reaction solution was separated by direct column chromatography to obtain the target product (37.8 mg, yield 66%).

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 compound represented by a formula (1) or a formula (2) or a formula (3) shown in the description. The method specifically comprises the steps of putting an o-amino nitrogen heterocyclic compound, a 2-oxo acetophenone derivative and a transition-metal salt catalyst into an organic solvent, carrying out a heated reaction in an oxygen-containing atmosphere, and subjecting the reaction solution to aftertreatment after the reaction ends, thereby obtaining the compound represented by the formula (1) or formula (2) or formula (3). 2-amino heterocyclic compounds are 2-aminopyridine compounds or 2-aminobenzo[d]thiazole compounds or 1-amino isoquinoline. According to the method disclosed by the invention, the operation is simple, the reaction conditions are mild, the byproduct is restricted to water, the reaction yield is high and reaches 97% to the maximum, and two kinds of heterocyclic compounds synthesized have pharmacological properties and can serve as important precursors of medicines.

Description

technical field [0001] The present invention relates to a preparation method of a C-3 oxygen substituted imidazole heterocyclic compound, in particular to C-3 oxygen substituted imidazo[1,2-a]pyridine and benzo[d]imidazo[2, 1-b] Synthetic method of thiazole heterocyclic compounds. Background technique [0002] In recent years, imidazo[1,2-a]pyridine and benzo[d]imidazo[2,1-b]thiazole have attracted the attention of chemists due to their wide applications in different fields. Imidazo[1,2-a]pyridine is an important class of nitrogen-containing heterocyclic compounds. This structure is one of the most common nitrogen-containing heterocycles in natural products and bioactive drug molecules. Wide range of uses. Two main synthetic methods have been reported so far, one is cyclization with 2-aminopyridine via oxidative amination or cascade reaction. The second is based on the nucleophilicity of the C-3 position of imidazo[1,2-a]pyridine, using a transition metal catalyst to acti...

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): C07D471/04C07D513/04A61P35/00A61P31/04
CPCC07D471/04C07D513/04
Inventor 张坚钟国富卢秀男
Owner 杭州尚合生物医药科技有限公司
Features
  • R&D
  • Intellectual Property
  • Life Sciences
  • Materials
  • Tech Scout
Why Patsnap Eureka
  • Unparalleled Data Quality
  • Higher Quality Content
  • 60% Fewer Hallucinations
Social media
Patsnap Eureka Blog
Learn More

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

© 2025 PatSnap. All rights reserved.Legal|Privacy policy|Modern Slavery Act Transparency Statement|Sitemap|About US| Contact US: help@patsnap.com