A kind of preparation method of imidazo[1,2-a]pyridine derivative

A 2-a, imidazolo technology, applied in the field of organic synthesis, can solve the problems of expensive reagents, high toxicity, lack of synthetic strategies, etc., and achieve the effect of simple operation and mild conditions

Active Publication Date: 2021-01-12
ZHENGZHOU UNIV
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  • Description
  • Claims
  • Application Information

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Problems solved by technology

Although there are many methods for synthesizing imidazo[1,2-a]pyridine compounds, these methods have some disadvantages, such as the need for expensive reagents, toxic raw materials or multi-step preparation of substrates, etc., especially for 3 -Phenoxyimidazo[1,2-a]pyridine derivatives, there is still a lack of effective and convenient synthetic strategies

Method used

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  • A kind of preparation method of imidazo[1,2-a]pyridine derivative
  • A kind of preparation method of imidazo[1,2-a]pyridine derivative
  • A kind of preparation method of imidazo[1,2-a]pyridine derivative

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0017] Example 1 Synthesis of 2-phenyl-3-phenoxyimidazo[1,2-a]pyridine

[0018] Under the protection of inert gas, add 2-phenoxyacetophenone (0.5 mmol, 106 mg), 2-aminopyridine (1.0 mmol, 100 mg), 15 ml 1,2-dichloroethane and Elemental iodine (0.5mmol, 137 mg) was then reacted in a 100º oil bath for 30 minutes. The reaction solution was washed with saturated sodium thiosulfate, water, and saturated brine respectively, the organic layer was dried over anhydrous sodium sulfate, and separated by column chromatography to obtain 143 mg of the corresponding imidazo[1,2-a]pyridine with a yield of 99.7%; 1 H NMR (400 MHz, CDCl 3 ) δ: 8.00-7.92 (m, 2H), 7.62 (dt, J = 6.8, 1.3 Hz, 1H), 7.57-7.50 (m, 1H), 7.33- 7.24 (m, 2H), 7.19 (dtd, J = 9.7, 7.3, 2.9 Hz, 3H), 7.07(ddd, J = 9.1, 6.7, 1.3 Hz, 1H), 6.99 (t, J = 7.3 Hz, 1H), 6.86 (dd, J = 7.7,1.5 Hz, 2H), 6.63 (td, J = 6.9, 1.1 Hz, 1H).

Embodiment 2

[0019] Example 2 Synthesis of 3-phenoxy-2-phenylbenzo[d]imidazo[2,1-b]thiazole

[0020] Under the protection of inert gas, 2-phenoxyacetophenone (0.5 mmol, 106 mg), 2-aminobenzothiazole (1.5 mmol, 226 mg), 15 ml of chloroform and elemental iodine (0.5 mmol , 137 mg), and then reacted in a 100 ºC oil bath for 70 minutes. The reaction solution was washed with saturated sodium thiosulfate, water, and saturated brine respectively, the organic layer was dried over anhydrous sodium sulfate, and separated by column chromatography to obtain 3-phenoxy-2-phenylbenzo[d]imidazo[2, 1-b] Thiazole 167 mg, yield 97.5%; 1 H NMR (400 MHz, CDCl3) δ: 7.95-7.87 (m, 2H), 7.73-7.65 (m, 1H), 7.52- 7.45 (m, 1H), 7.41-7.28 (m, 6H), 7.25- 7.21 ( m, 1H), 7.17 – 7.05 (m, 3H).

Embodiment 3

[0021] Example 3 Synthesis of 2-(4-bromophenyl)-3-phenoxyimidazo[1,2-a]pyridine

[0022] Under the protection of inert gas, 1-(4-bromophenyl)-2-phenoxy-1-one (0.5 mmol, 146 mg), 2-aminopyridine (1.5 mmol, 149 mg), 15 ml of 1,2-dichloroethane and elemental iodine (1 mmol, 274 mg) were reacted in an oil bath at 100 ºC for 40 minutes. The reaction solution was washed with saturated sodium thiosulfate, water, and saturated brine respectively, the organic layer was dried over anhydrous sodium sulfate, concentrated under reduced pressure, and separated by column chromatography to obtain 2-(4-bromophenyl)-3-phenoxy Imidazo[1,2-a]pyridine 182 mg, yield 99.2%; 1 H NMR (400 MHz, CDCl 3 ) δ: 8.15 (d, J = 9.1 Hz,1H), 8.06 -7.97 (m, 2H), 7.92 (dd, J = 6.6, 1.2 Hz, 1H), 7.61- 7.50 (m, 3H),7.41-7.32 (m, 2H), 7.23-7.14 (m, 1H), 7.08 (t, J = 6.8 Hz, 1H), 7.00-6.92 (m, 2H).

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Abstract

The invention discloses a preparation method of an imidazole-[1,2-a]-pyridine derivative, and belongs to the field of organic synthesis. The preparation method comprises the following steps of using 2-phenoxyacetophenone as a starting raw material, using elemental iodine as a catalyst, and reacting with the 2-phenoxyacetophenone; separating by column chromatography, so as to obtain the imidazole-[1,2-a]-pyridine derivative. Compared with the prior art, the preparation method has the advantages that the reaction yield rate is high, the post-treatment is simple, and the preparation method is more suitable for industrialized production. The prepared imidazole-[1,2-a]-pyridine derivative can be used as a medicine precursor, be used for synthesizing antifungal, anti-inflammatory, antitumor, antivirus, antibacterial, antiprotozoal, antipyretic, analgesic and antiapoptotic medicines and the like, and be applied to the fields of organic photoelectric materials, medicines, biological probes, fluorescent dyes and the like.

Description

technical field [0001] The invention belongs to the field of organic synthesis, and relates to a synthesis method of a class of imidazo[1,2-a]pyridine derivatives, in particular to a preparation method of substituted 3-phenoxyimidazo[1,2-a]pyridine derivatives . Background technique [0002] Imidazopyridines are a class of nitrogen-containing heterocyclic compounds with important biological activities. The imidazo[1,2-a]pyridine unit structure widely exists in natural products and drug molecules, and its derivatives exhibit a wide range of biological activities, such as antifungal, anti-inflammatory, antitumor, antiviral, antibacterial, antibiotic Animals, antipyretic, analgesic, anti-apoptotic, etc. Among them, imidazo[1,2-a]pyridine compounds substituted at the C-3 position can be used as metabotropic glutamate receptor 2 modulators (I), anticancer drugs (II), and osteoporosis drugs (III) , neurotransmitter inhibitors (IV), etc. In addition, imidazo[1,2-a]pyridine also...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D471/04C07D513/04
CPCC07D471/04C07D513/04
Inventor 郭艳春王月秀曹书霞赵玉芬
Owner ZHENGZHOU UNIV
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