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Preparation method of heteroaromatic iminazole [1,2-Alpha]pyridine compounds

A technology for heteroaromatic imidazole and aryl imidazole is applied in the field of preparation of heteroaromatic imidazo[1,2-a]pyridine compounds, and can solve the problems of complicated conditions, low atom economy, poor selectivity and the like , to achieve the effect of large application potential, simple reaction conditions and high atom economy

Inactive Publication Date: 2014-12-17
WUHAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Although these methods can prepare the target product, the starting materials used in the reaction are relatively complicated, the conditions are relatively cumbersome, the atom economy of the reaction is generally low, and the selectivity is not very good.

Method used

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  • Preparation method of heteroaromatic iminazole [1,2-Alpha]pyridine compounds
  • Preparation method of heteroaromatic iminazole [1,2-Alpha]pyridine compounds
  • Preparation method of heteroaromatic iminazole [1,2-Alpha]pyridine compounds

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Experimental program
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Effect test

Embodiment 1

[0010] In the Schlenk reaction tube, add 2-aminopyridine (1.0mmol), silver carbonate (1.0mmol), replace the system with nitrogen protection, add 6 milliliters of 1,4-dioxane, phenylacetylene (0.5mmol), in 100 °C for 10 hours. Stop the reaction, filter the reaction system with diatomaceous earth, wash the filter residue with 20-30 ml of dichloromethane, and combine the filtrates. The product imidazo[1,2-a]pyridine compound was obtained by column chromatography. (The product can also be obtained by using other conventional separation and purification methods.)

Embodiment 2

[0012] In the Schlenk reaction tube, add 2-aminopyridine (1.5mmol), silver oxide (1.0mmol), replace the system with nitrogen protection, add 6 milliliters of 1,4-dioxane, phenylacetylene (0.5mmol), at 110 °C for 10 hours. Stop the reaction, filter the reaction system with diatomaceous earth, wash the filter residue with 20-30 ml of dichloromethane, and combine the filtrates. The product imidazo[1,2-a]pyridine compound was obtained by column chromatography.

Embodiment 3

[0014] In the Schlenk reaction tube, add 2-aminopyridine (1.0mmol), silver carbonate (1.0mmol), replace the system with nitrogen protection, add 6 milliliters of N,N-dimethylformamide, phenylacetylene (0.5mmol), in The reaction was carried out at 120° C. for 15 hours. Stop the reaction, filter the reaction system with diatomaceous earth, wash the filter residue with 20-30 ml of dichloromethane, and combine the filtrates. The product imidazo[1,2-a]pyridine compound was obtained by column chromatography.

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Abstract

The invention relates to a preparation method of heteroaromatic iminazole [1,2-Alpha]pyridine compounds. The method comprises the steps that under the existence of univalent silver salt, 2-amino pyridine compounds and acetylene compounds are dissolved in organic solvents to be reacted for 10 to 24 hours at the reacting temperature of 100 to 130 DEG C, and then the compounds are separated and purified to prepare the heteroaromatic iminazole [1,2-Alpha]pyridine compounds. The reacting compounds used in the method of the utility model can be simply prepared at a low cost, the reacting condition is very simple, atom economy is very high, and the oxidation cyclization reaction of the 2-amino pyridine compounds and the acetylene compounds can be realized in a highly selective mode, so as to prepare the heteroaromatic iminazole [1,2-Alpha]pyridine compounds. The method can prepare the prodrug of a drug with adone zoli pyridine simply, and the drug is widely applied to treating gastric ulcers and gastroesophageal reflux diseases. The preparation method provided by the invention has great application potential for synthetizing medicine, natural products and the like.

Description

technical field [0001] The invention relates to a preparation method of a heteroaromatic ring imidazo[1,2-a]pyridine compound Background technique [0002] Heteroaromatic imidazo[1,2-a]pyridine compounds are a very important class of nitrogen-containing fused heterocyclic compounds, and their skeletons are widely found in many natural products and drugs with biological activity. Because of its special physiological activity and medicinal properties, it has always been a research hotspot of organic chemists and medicinal chemists. Especially imidazo[1,2-a]pyridine compounds, many of which have antiviral, antibacterial, antimicrobial and anticytokinin activities, and some of them can also be used as drugs for the treatment of gastric ulcer, diabetes and psychosis. The traditional preparation methods of imidazo[1,2-a]pyridine compounds mainly include the reaction of 2-aminopyridine with a-halogenated carbonyl compounds or the reaction of 2-aminopyridine with aldehyde compounds...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D471/04
Inventor 雷爱文何川
Owner WUHAN UNIV
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