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Synthesis method of 3-nitro-imidazo [1,2-a] pyridine derivative

A technology of pyridine derivatives and synthetic methods, applied in the field of organic chemical synthesis, can solve the problems of use, low product yield, non-reusable use, etc., and achieve the effects of mild reaction conditions, cheap and easy-to-obtain solvents, and fewer operation steps

Inactive Publication Date: 2015-11-25
HEBEI NORMAL UNIV
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Problems solved by technology

[0012] As mentioned above, although the preparation of 3-nitroimidazo[1,2- a ] a variety of methods for pyridine derivatives, but there are some defects in the above-mentioned different synthetic methods, such as the use of harmful, non-reusable organic solvents, long reaction times, or low product yields, or the use of expensive and unavailable organic solvents. Recycled catalyst, not conducive to industrial production

Method used

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  • Synthesis method of 3-nitro-imidazo [1,2-a] pyridine derivative
  • Synthesis method of 3-nitro-imidazo [1,2-a] pyridine derivative
  • Synthesis method of 3-nitro-imidazo [1,2-a] pyridine derivative

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Embodiment 1

[0029] The present embodiment is 3-nitro-2-phenylimidazo[1,2- a ] The synthesis of pyridine is raw material with nitromethane, 2-aminopyridine and benzaldehyde, and its reaction formula is as follows:

[0030]

[0031] Experimental procedure: 2-aminopyridine (1.0mmol), benzaldehyde (1.05mmol), nitromethane (1.1mmol) and CoFe 2 o 4 / CNT-Cu nanoparticles (0.05mmol) were added to PEG400 (5ml), stirred at 80°C for an appropriate time. After completion of the reaction (monitored by thin layer chromatography), the reaction mixture was cooled to room temperature, extracted with ethyl acetate (3 x 10 mL), and the catalyst was recovered magnetically. MgSO for organic layer 4 Dry and concentrate by distillation under reduced pressure. The crude product was purified by column chromatography to obtain the target product (95% yield).

[0032] Product data: yellow solid, melting point: 176-177°C; 1 HNMR (CDCl 3 ,500MHz)δ7.31-7.28(m,1H),7.51(t, J =3.0Hz,3H),7.68-7.65(m,1H),7.85(d,...

Embodiment 2

[0034] The present embodiment is 3-nitro-2-(4-methylphenyl)-imidazo[1,2- a ] The synthesis of pyridine is raw material with nitromethane, 2-aminopyridine and 4-methylbenzaldehyde, and its reaction formula is as follows:

[0035]

[0036] Experimental procedure: 2-aminopyridine (1.0mmol), 4-methylbenzaldehyde (1.05mmol), nitromethane (1.1mmol) and CoFe 2 o 4 - Add CNT-Cu nanoparticles (0.05mmol) to PEG400 and stir at 80°C for an appropriate time. After completion of the reaction (monitored by thin layer chromatography), the reaction mixture was cooled to room temperature and extracted with EtOAc (3 x 10 mL). MgSO for organic layer 4 Dry and concentrate by distillation under reduced pressure. The crude product was purified by column chromatography to obtain the target product (92% yield).

[0037] Product data: yellow solid, melting point: 201-202°C; 1 HNMR (CDCl 3 ,500MHz)δ2.45(s,3H),7.28-7.26(m,1H),7.32(d, J =8.0Hz,2H),7.65(t, J =7.0Hz,1H),7.83(d, J =8.0Hz,3H),9.5...

Embodiment 3

[0039]The present embodiment is 3-nitro-2-(4-methoxyphenyl)-imidazo[1,2- a ] The synthesis of pyridine is raw material with nitromethane, 2-aminopyridine and 4-methoxybenzaldehyde, and its reaction formula is as follows:

[0040]

[0041] Experimental procedure: 2-aminopyridine (1.0mmol), 4-methoxybenzaldehyde (1.05mmol), nitromethane (1.1mmol) and CoFe 2 o 4 - Add CNT-Cu nanoparticles (0.05mmol) to PEG400 and stir at 80°C for an appropriate time. After completion of the reaction (monitored by thin layer chromatography), the reaction mixture was cooled to room temperature and extracted with EtOAc (3 x 10 mL). MgSO for organic layer 4 Dry and concentrate by distillation under reduced pressure. The crude product was purified by column chromatography to obtain the target product (yield 88%).

[0042] Product data: yellow solid, melting point: 171-172°C; 1 HNMR (CDCl 3 ,500MHz)δ3.90(s,3H),7.04(d, J =9.0Hz,2H),7.28-7.25(m,1H),7.67-7.63(m,1H),7.82(d, J =8.5Hz,1H),7.95(d,...

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Abstract

The present invention discloses a chemical synthesis method of 3-nitro-imidazo [1,2-a] pyridine derivative. The method is as below: fully reacting raw materials of aromatic aldehyde, 2-amino-pyridine, derivatives thereof and nitromethane in polyethylene glycol under the catalysis of a magnetic carbon nanotube loaded Cu (CoFe2O4 / CNT-Cu) at 80 DEG C to prepare 3-nitroimidazo [1,2-a] pyridine derivative. The invention has the advantages of reasonable process, readily available reaction raw materials, easy preparation of the catalyst, mild reaction conditions, recyclable solvent system, one-step reaction to obtain the desired product, and high product yield, and provides a green synthetic route for synthesis of 3-nitro-imidazo [1,2-a] pyridine derivative.

Description

technical field [0001] The invention relates to a method for synthesizing organic matter, in particular to a method for synthesizing imidazo[1,2-a]pyridine derivatives, and belongs to the technical field of organic chemical synthesis. Background technique [0002] imidazo[1,2- a ] Pyridine derivatives are heterocyclic compounds with significant biological activity, have antibacterial, antiviral, anti-tuberculosis properties, are inhibitors of VEGFR2 kinase, IGF-1R tyrosine kinase and ASK1, and have antiepileptic properties activity. Imidazo[1,2-α]pyridine derivatives exist in natural products and are pharmacologically important organic molecules. Exemplary of these compounds include alpitant, zolpidem, miprofen, necopitant, and mesyridine. For imidazo[1,2- a ] The synthesis of pyridine derivatives, people have developed a variety of chemical synthesis methods and routes. For example, starting from nitrostyrene and 2-aminopyridine, using N-substituted 2-aminopyridine as ...

Claims

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Application Information

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IPC IPC(8): C07D471/04
CPCC07D471/04Y02P20/584
Inventor 张占辉芦军马翠廷默丽萍
Owner HEBEI NORMAL UNIV
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