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A kind of preparation method of imidazole heterocyclic compound substituted by C-3 position oxygen

A technology of compounds and synthetic methods, applied in the directions of organic chemistry, drug combination, anti-tumor drugs, etc., to achieve the effects of high economic benefit, good economic value and wide application range

Active Publication Date: 2019-05-17
杭州尚合生物医药科技有限公司 +1
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  • 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

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  • A kind of preparation method of imidazole heterocyclic compound substituted by C-3 position oxygen
  • A kind of preparation method of imidazole heterocyclic compound substituted by C-3 position oxygen
  • A kind of preparation method of imidazole heterocyclic compound substituted by C-3 position oxygen

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 (0.01mmol) , 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%).

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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

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Application Information

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Patent Type & Authority Patents(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
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