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Method for synthesizing 2-arylimidazo[1, 2-a]pyridine compounds from ethylbenzene compounds

A technology of aryl imidazo and compound, which is applied in the field of synthesis of 2-aryl imidazo[1,2-a]pyridine derivatives, can solve the problems of expensive raw materials, complicated operation, severe reaction conditions, etc., and achieve reduction The effect of three waste discharge and high reaction yield

Inactive Publication Date: 2018-11-16
HENAN NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0003] Many methods for the synthesis of 2-arylimidazo[1,2-a]pyridine derivatives have been reported so far, the most classic method is to use 2-bromoacetophenone as raw material and α-aminopyridine It is prepared by cyclization reaction, in addition to the cross-coupling reaction of imidazo[1,2-a]pyridine using arylating reagents to prepare such derivatives and the conversion of acetophenone to imidazopyridine catalyzed by cuprous iodide However, these synthetic methods generally have disadvantages such as expensive raw materials, complicated operations, severe reaction conditions and difficult control.

Method used

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  • Method for synthesizing 2-arylimidazo[1, 2-a]pyridine compounds from ethylbenzene compounds
  • Method for synthesizing 2-arylimidazo[1, 2-a]pyridine compounds from ethylbenzene compounds
  • Method for synthesizing 2-arylimidazo[1, 2-a]pyridine compounds from ethylbenzene compounds

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Experimental program
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Effect test

Embodiment 1

[0021] Synthesis of 2-phenylimidazo[1,2-α]pyridine

[0022]

[0023] Add 3mL of water, 30μL of Tween, 0.5mmol of ethylbenzene, 1.5mmol of NBS and 0.05mmol of AIBN into a 25mL reaction flask, react at 60°C for 4 hours, then add 2.0mmol of sodium bicarbonate and 0.5mmol of α-aminopyridine, React at 80°C for 2 hours. After the reaction, add ethyl acetate, add saturated brine for extraction, concentrate the organic phase, and obtain 80 mg of white solid with a yield of 82% by column chromatography.

[0024] Product characterization: 1 H NMR (CDCl 3 ,600MHz)δ:8.10(d,J=6.8Hz,1H),7.96(d,J=7.2Hz,2H), 7.85(s,1H),7.63(d,J=9.1Hz,1H),7.45- 7.42 (m, 2H), 7.35-7.31 (m, 1H), 7.18-7.14 (m, 1H), 6.78-6.75 (m, 1H).

Embodiment 2

[0026] Synthesis of 6-methyl-2-phenylimidazo[1,2-α]pyridine

[0027]

[0028] Add 3mL of water, 30μL of Tween, 0.5mmol of ethylbenzene, 1.5mmol of NBS and 0.05mmol of AIBN into a 25mL reaction flask, react at 60°C for 4 hours, then add 2.0mmol of sodium bicarbonate and 0.5mmol of 2-amino-5 - picoline, reacted at 80° C. for 2 h, after the reaction, added ethyl acetate, added saturated brine for extraction, concentrated the organic phase, and obtained 85 mg of white solid by column chromatography with a yield of 82%.

[0029] Product characterization: 1 H NMR (CDCl 3 ,600MHz)δ:7.93(d,J=7.5Hz,2H),7.84(s,1H),7.73(s,1H),7.52(d,J=9.1Hz,1H),7.42(t,J=7.3 Hz, 2H), 7.31(t, J=7.2Hz, 1H), 6.99(d, J=9.1Hz, 1H), 2.28(s, 3H).

Embodiment 3

[0031] Synthesis of 7-methyl-2-phenylimidazo[1,2-α]pyridine

[0032]

[0033] Add 3mL of water, 30μL of Tween, 0.5mmol of ethylbenzene, 1.5mmol of NBS and 0.05mmol of AIBN into a 25mL reaction flask, and react at 60°C for 4 hours, then add 2.0mmol of potassium carbonate and 0.5mmol of 2-amino-4- The picoline was reacted at 80° C. for 2 h. After the reaction, ethyl acetate was added, extracted with saturated brine, the organic phase was concentrated, and column chromatography gave 82 mg of a white solid with a yield of 79%.

[0034] Product characterization: 1 H NMR (CDCl 3 ,600MHz)δ:7.93-7.92(m,3H),7.73(s,1H),7.41(t,J=7.1Hz,2H),7.37(s,1H),7.31(t,J=7.1Hz,1H ), 6.56 (d, J=6.6Hz, 1H), 2.37 (s, 3H).

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Abstract

The invention discloses a method for synthesizing 2-arylimidazo[1, 2-a]pyridine compounds from ethylbenzene compounds and belongs to the field of 2-arylimidazo[1, 2-a]pyridine derivative synthesis. The method comprises that an ethylbenzene compound, a phase transfer catalyst, N-bromosuccinimide NBS and AIBN are added into water, the solution undergoes a reaction at 60 DEG C, an inorganic base andan alpha-aminopyridine compound are added into the reaction product, and the mixture undergoes a reaction at 80 DEG C to produce the 2-arylimidazo[1, 2-a]pyridine compound. The method creatively utilizes the ethylbenzene compound to synthesize the 2-arylimidazo[1, 2-a]pyridine compound. Compared with the 2-bromoacetophenone commonly used as a 2-arylimidazo[1, 2-a]pyridine compound synthesis raw material in the industry, the ethylbenzene compound is cheaper and more easily available.

Description

technical field [0001] The invention belongs to the technical field of synthesis of 2-aryl imidazo[1,2-a]pyridine derivatives, in particular to a synthesis of 2-aryl imidazo[1,2-a]pyridines from ethylbenzene compounds compound method. Background technique [0002] As a very important class of heterocyclic compounds, 2-arylimidazo[1,2-a]pyridine derivatives have good biological activity and are common heterocyclic compounds in natural products and medicines. Listed drugs such as zolpidem, zolimidine, and salipidem all use this group as the mother nucleus. Therefore, the development of new research methods is of great significance to the synthesis of these drugs and the discovery of new drugs. [0003] Many methods for the synthesis of 2-arylimidazo[1,2-a]pyridine derivatives have been reported so far, the most classic method is to use 2-bromoacetophenone as raw material and α-aminopyridine It is prepared by cyclization reaction, in addition to the cross-coupling reaction o...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D471/04
CPCC07D471/04
Inventor 赵明豪马春华张淑婷杨笑曾文杰
Owner HENAN NORMAL UNIV