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A kind of imidazo[1,2-a]pyrimidine compound and its preparation method

A 2-a, imidazolo technology, applied in the field of imidazo[1,2-a]pyrimidine compounds and their preparation, can solve the problem of not containing functional groups, etc., and achieve the effect of simple operation steps, mild reaction conditions and convenient raw materials

Active Publication Date: 2022-04-26
LUDONG UNIVERSITY
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  • Abstract
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  • Application Information

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Problems solved by technology

At present, the synthesis method of this type of compound mostly uses three-component coupling reaction of aldehyde, alkyne and amine (A 3 coupling) and subsequent intramolecular nucleophilic addition reactions, the constructed imidazo[1,2-a]pyrimidine skeleton does not contain functional groups that are easy to further modify

Method used

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  • A kind of imidazo[1,2-a]pyrimidine compound and its preparation method
  • A kind of imidazo[1,2-a]pyrimidine compound and its preparation method
  • A kind of imidazo[1,2-a]pyrimidine compound and its preparation method

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Embodiment

[0032] The preparation method of phenyl (4-phenylbenzo [4,5] imidazo [1,2-a] pyrimidin-2-yl) ketone, concrete steps are as follows:

[0033] 2-Aminobenzimidazole (II) (133.2mg, 1.0mmol, 1.0eq.), phenylglyoxal (III) (536.6mg, 2.0mmol, 1.0eq.) was added to the dried Add 1.5mL of anhydrous DCM to the reaction bottle of the child, after reacting at room temperature for 2h, extract with DCM (dichloromethane) (10mL×3 times), combine the extracts, remove the solvent under reduced pressure, and perform silica gel column chromatography Separation (PE:EA=4:1, that is, according to the volume ratio, petroleum ether:ethyl acetate=4:1) to obtain phenyl (4-phenylbenzo[4,5]imidazo[1,2-a] Pyrimidin-2-yl)methanone (I) (279.5 mg, 80%). After NMR analysis, the NMR spectrum data is 1 HNMR (500MHz, CDCl 3 )δ7.34(d,J=7.5Hz,2H),7.97(d,J=8.5Hz,1H),7.68-7.56(m,6H),7.47-7.44(m,4H),7.06(t,J =8.0Hz,1H)6.75(d,J=8.5Hz,1H); 13 C NMR (126MHz, CDCl 3 )δ191.16,157.57,150.59,149.94,145.59,134.99,133.70,13...

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Abstract

The invention discloses an imidazo[1,2-a]pyrimidine compound and a preparation method thereof. The compound is phenyl(4-phenylbenzo[4,5]imidazo[1,2-a]pyrimidine- 2-yl)methanone is a compound synthesized by one-step reaction with 2-aminobenzimidazole and phenylglyoxal as starting raw materials. The imidazo[1,2‑a]pyrimidine skeleton is an important pharmacophore. Compounds containing this skeleton often have a wide range of biological activities, such as antibacterial, anti-inflammatory, antipyretic, hypnotic, etc. The synthesis of such compounds is of great importance The development of new drugs is of great significance. The preparation method of the invention has convenient and easy-to-obtain raw materials, simple operation steps and mild reaction conditions, is a new method for preparing imidazo[1,2-a]pyrimidine compounds, and is suitable for the needs of large-scale industrial production.

Description

technical field [0001] The invention belongs to the technical field of fine chemicals, and in particular relates to an imidazo[1,2-a]pyrimidine compound and a preparation method thereof. Background technique [0002] The imidazo[1,2-a]pyrimidine skeleton is an important pharmacophore. Compounds containing this skeleton often have a wide range of biological activities, such as antibacterial, anti-inflammatory, antipyretic, hypnotic, etc. The synthesis of such compounds is of great importance The development of new drugs is of great significance. At present, the synthesis method of this type of compound mostly uses three-component coupling reaction of aldehyde, alkyne and amine (A 3 coupling) and the subsequent intramolecular nucleophilic addition reaction, the constructed imidazo[1,2-a]pyrimidine skeleton does not contain functional groups that are easy to be further modified. Structural modification and structure-activity relationship analysis are key steps in the developm...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D487/04
CPCC07D487/04
Inventor 赵西梅王光辉贾健刘希光
Owner LUDONG UNIVERSITY