Synthetic method of imidazo[1,2-a]pyridine

A synthesis method, 2-a technology, applied in the direction of organic chemistry, etc., can solve the problems of harsh reaction conditions, lack, low yield, etc., and achieve the effects of being conducive to industrial production, mild reaction conditions, and simple process flow

Inactive Publication Date: 2016-07-27
NORTHWEST UNIV(CN)
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, there are some shortcomings in the existing methods for synthesizing imidazo[1,2-a]pyridine, such as long reaction time, harsh reaction conditions, low yield, difficult raw materials, expensive catalysts, lack of deficiencies, etc. These shortcomings are all To a certain extent, the industrial synthesis of imidazo[1,2-a]pyridine derivatives is limited

Method used

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  • Synthetic method of imidazo[1,2-a]pyridine
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  • Synthetic method of imidazo[1,2-a]pyridine

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0019] Example 1: Synthesis of 2-phenyl-3-benzoylimidazo[1,2-a]pyridine (1a)

[0020] Add 1.2mmol of 2-aminopyridine, 1.0mmol of chalcone, 20mol% iodine and 5mL of 1,2-dichloroethane into a 25mL round bottom flask, and heat the mixture at 110 o C under stirring for 10 h, and the progress of the reaction was detected by a thin-layer chromatographic plate. After the reaction was completed, it was washed with saturated sodium thiosulfate solution, extracted with ethyl acetate (15 mL×3), washed with saturated brine, and dried over anhydrous sodium sulfate. After concentrated by vacuum distillation, silica gel column chromatography with ethyl acetate / petroleum ether (1:2) gave 256 mg of a yellow solid with a yield of 86%.

[0021] Characterization data: Mp121~122°C; 1 HNMR (400MHz, CDCl 3 )δ9.56(d,J=7.0Hz,1H),7.81(d,J=8.9Hz,1H),7.58–7.48(m,3H),7.32(dd,J=5.1,3.1Hz,2H), 7.29–7.23(m,1H),7.17–7.05(m,6H); 13 CNMR (101MHz, CDCl 3 )δ187.37,154.99,147.42,138.66,133.99,131.75,130.20,1...

Embodiment 2

[0023] Similar to the examples, the difference is that copper chloride or copper acetate is used as a catalyst, and chlorobenzene is a solvent, and the temperature of reaction is 120 o C, reacted for 12 hours, washed with water to remove copper ions, there were still residues detected by ICP, and the reaction yield was 70%.

Embodiment 3

[0024] Example 3: Synthesis of 7-methyl 2-phenyl-3-benzoylimidazo[1,2-a]pyridine (1c)

[0025] Add 1.2mmol of 2-amino-4-picoline, 1.0mmol of chalcone, 20mol% iodine and 5mL of 1,2-dichloroethane into a 25mL round-bottomed flask, and put the Mixture at 110 o C under stirring for 10 h, and the progress of the reaction was detected by a thin-layer chromatographic plate. After the reaction was completed, it was washed with saturated sodium thiosulfate solution, extracted with ethyl acetate (15 mL×3), washed with saturated brine, and dried over anhydrous sodium sulfate. After concentrated by distillation under reduced pressure, it was chromatographed on silica gel with ethyl acetate / petroleum ether (1:3) to obtain 265 mg of a yellow solid with a yield of 85%.

[0026] Characterization data: Mp137?138°C; 1 HNMR (400MHz, CDCl 3 )δ9.45(d,J=7.1Hz,1H),7.56(s,1H),7.52–7.47(m,2H),7.32–7.28(m,2H),7.24(d,J=7.5Hz,1H ),7.16–7.03(m,5H),6.94(dd,J=7.1,1.4Hz,1H),2.52(s,3H);13CNMR(1MHz,CDCl ...

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Abstract

The invention discloses a novel method for synthesizing imidazo[1,2-a]pyridine. According to the method, imidazo[1,2-a]pyridine is synthesized from 2-aminopyridine and chalcone through oxidization cyclization by taking 1,2-dichloroethane as a solvent and iodine as a catalyst. The method has the advantages that the operation is simple, the raw materials are easily available, reaction conditions are mild, the yield is relatively high, and the practicability is strong. The method is applicable to industrial production.

Description

technical field [0001] The invention relates to a synthesis method of imidazo[1,2-a]pyridine, which belongs to the field of organic chemistry. Background technique [0002] Imidazo[1,2-a]pyridine is an important nitrogen-containing heterocyclic aromatic compound, and imidazo[1,2-a]pyridine-based derivatives have been widely used in chemistry, pharmacy and This also makes imidazo[1,2-a]pyridine derivatives a very important class of structures in nitrogen heterocyclic compounds. Imidazo[1,2-a]pyridine is widely used in the fields of medicinal chemistry and material science, and is the main component of some important drugs, such as saripidem, zolimidine, zolpidem, etc. all contain imidazo[1,2-a]pyridine. The structure of 1,2-a]pyridine. Imidazo[1,2-a]pyridine derivatives also have good biological activities, such as anti-virus, anti-tumor, anti-inflammatory, sedative-hypnotic and anti-ulcer. At present, the method of synthesizing imidazo[1,2-a]pyridine is mainly prepared by...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D471/04
CPCC07D471/04
Inventor 李剑利朱月路李成刘萍王亚棋
Owner NORTHWEST UNIV(CN)
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