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Simple method for synthesizing imidazo (1,2-a) pyridine derivatives

A technology for synthesizing imidazole and 2-a, which is applied in organic chemistry and other fields, can solve problems such as unfavorable industrial production, high reaction temperature, and long reaction time, and achieve good regioselectivity, mild reaction conditions, and short process flow

Active Publication Date: 2014-06-11
JINTAN DEPEI CHEM
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

The above-mentioned synthetic method of combining different raw materials, some synthetic raw materials are toxic, and some require higher reaction temperature and longer reaction time, which is not conducive to industrial production; or as a substrate is not conducive to expanding the structural diversity of products ; Some use metal catalysts that will leave metal components in the target product in the synthesis reaction, etc.
It can be seen that although there are many synthetic methods that have been disclosed so far, their shortcomings are urging scholars in the industry to develop green synthetic imidazo[1,2- a A New Method of Pyridine Derivatives

Method used

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  • Simple method for synthesizing imidazo (1,2-a) pyridine derivatives
  • Simple method for synthesizing imidazo (1,2-a) pyridine derivatives
  • Simple method for synthesizing imidazo (1,2-a) pyridine derivatives

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Experimental program
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Effect test

Embodiment 1

[0035] Embodiment 1: This embodiment is 3-nitro-2-phenyl-imidazo[1,2- a ] the synthesis of pyridine; With 2-aminopyridine and β-nitrostyrene as raw material, its reaction formula is as follows:

[0036]

[0037] Implementation steps:

[0038] 0.094 g (1 mmol) of 2-aminopyridine, 0.156 g (1.05 mmol) of β-nitrostyrene, 0.051 g (0.2 mmol) of iodine, 0.180 g (2 mmol) of tert-butanol peroxide and 0.049 g (0.62 mmol) of pyridine mmol) was placed in a reaction flask, 10 mL of methanol was added, heated to reflux (the temperature of the reaction solution was about 65° C.), and TLC was followed until the reaction was completed. After cooling to room temperature, methanol was removed by rotary evaporation, and the concentrated product was separated by chromatographic column to obtain the target product (yield 90%).

[0039] Product data: M.P. 172-174 ℃; 1 H NMR (400 MHz, CDCl 3 ) δ = 9.53 (d, J =6.9, 1H), 7.89 (dd, J=22.8, 5.7, 3H), 7.67 (t, J =7.9, 1H), 7.52 (d, J =2.6, ...

Embodiment 2

[0040] Embodiment 2: This embodiment is 3-nitro-2-(4-methylphenyl)-imidazo[1,2- a ] pyridine synthesis; with 2-aminopyridine and 4-methyl-β-nitrostyrene as raw materials, its reaction formula is as follows:

[0041]

[0042] Implementation steps:

[0043] 0.094 grams (1 mmol) of 2-aminopyridine, 0.171 grams (1.05 mmol) of 4-methyl-β-nitrostyrene, 0.051 grams (0.2 mmol) of iodine, 0.180 grams (2 mmol) of tert-butanol peroxide and Pyridine 0.049 g (0.62 mmol) was placed in a reaction flask, 10 mL of ethanol was added, heated to reflux (the temperature of the reaction solution was about 79° C.), followed by TLC until the reaction was completed. After cooling to room temperature, the ethanol was removed by rotary evaporation, and the concentrated product was separated by chromatographic column to obtain the target product (yield 87%).

[0044] Product data: M.P. 204-206 ℃; 1 H NMR (400 MHz, CDCl 3 ) δ = 9.51 (d, J =6.9, 1H), 7.83 (d, J =8.0, 3H), 7.64 (t, J =7.9, 1H...

Embodiment 3

[0045] Embodiment Three: This embodiment is 2-(4-methoxyphenyl)-3-nitro-imidazo[1,2- a ] The synthesis of pyridine; With 2-aminopyridine and 4-methoxy-β-nitrostyrene as raw material, its reaction formula is as follows:

[0046]

[0047] Implementation steps:

[0048] (1) 0.094 grams (1 mmol) of 2-aminopyridine, 0.283 grams (1.05 mmol) of 4-methoxy-β-nitrostyrene, 0.051 grams (0.2 mmol) of iodine, and 0.180 grams of tert-butanol peroxide ( 2 mmol) and 0.049 g (0.62 mmol) of pyridine were placed in a reaction flask, 10 mL of n-propanol was added, heated to reflux (the temperature of the reaction solution was about 97°C), and TLC was followed until the end of the reaction. After cooling to room temperature, propanol was removed by rotary evaporation, and the concentrated product was separated by chromatography column to obtain the target product (yield 85%).

[0049] Product Data: M.P. . 155-157℃; 1 H NMR (400 MHz, CDCl 3 ) δ 9.32 (d, J = 6.0 Hz, 1H), 7.94 (d, J =...

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Abstract

The invention relates to a simple method for synthesizing imidazo (1,2-a) pyridine derivatives. The method comprises the steps of: dissolving reactants including 2-aminopyridine or derivatives thereof and beta-nitrostyrolene or derivatives thereof into a solvent, and preparing the imidazo (1,2-a) pyridine at 25DEG C-150DEG C by taking iodine and pyridine as catalysts and t-butylhydroperoxide as an oxidant, wherein the mole ratio of 2-aminopyridine or derivatives thereof to beta-nitrostyrolene or derivatives thereof to iodine to t-butylhydroperoxide to pyridine is 1:(0.9-1.5):(0.1-0.5):(1-4):(0.3-1). The simple method uses low-cost and easily available reaction raw materials and catalysts, is short in technological process, mild in reaction conditions, and easy for the expansion of the product structure; the target product can be obtained in one step through the implemented serial reaction; the catalyst is a nonmetal system, thus having metal residue risk. The method is high-efficiency, economical and environmentally-friendly synthesis route.

Description

technical field [0001] The invention relates to the technical field of organic synthesis, in particular to the preparation of pharmaceutical compounds imidazo[1,2- a ] pyridine synthesis technology, specifically proposed the synthesis of imidazo[1,2- a ] A facile method for pyridine derivatives. Background technique [0002] imidazo[1,2- a ] Pyridine, as an important class of heterocycles, is the core fragment of many important compounds in chemical agents. Because some derivatives containing these core fragment skeletons have antibacterial, antiviral, anti-inflammatory, anti-ulcer, anti-tuberculosis, anti-cancer and other active characteristics, they have attracted widespread attention in the fields of pharmacy, biology, and medicine. Prior art, for imidazo[1,2- a The synthetic techniques of ]pyridine have been studied to a certain extent, and it is reported that there are synthetic methods using a variety of different precursors and strategies: For example: using β-dic...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D471/04
CPCC07D471/04
Inventor 安礼涛陈雄朱凤霞黄其赞张路路周建峰吕蒙安晓伟
Owner JINTAN DEPEI CHEM
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