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Copper-catalyzed synthetic method of imidazo[1,2-a]pyridine-3-formaldehyde compound

A synthetic method and imidazo technology, applied in the field of organic synthesis chemistry, can solve problems such as low yield, numerous precursor steps, harsh reaction conditions, etc., and achieve the effects of simple operation, shortened reaction time, and high-efficiency and high-yield synthesis.

Inactive Publication Date: 2013-12-11
NORTHEAST NORMAL UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Targetedly solve the problems of low Vilsmeier–Haack formylation yield (20–30%), harsh reaction conditions, and many steps in the precursor of intramolecular dehydrocyclization reaction

Method used

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  • Copper-catalyzed synthetic method of imidazo[1,2-a]pyridine-3-formaldehyde compound
  • Copper-catalyzed synthetic method of imidazo[1,2-a]pyridine-3-formaldehyde compound
  • Copper-catalyzed synthetic method of imidazo[1,2-a]pyridine-3-formaldehyde compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0020] Example 1 Imidazo[1,2-a]pyridine-3-carbaldehyde derivatives 3a preparation of

[0021]

[0022] Add to a 25 mL round bottom flask with a magnetic stirrer N, N - Dimethylformamide (DMF) (2 mL), cinnamaldehyde 1a (0.5 mmol), 2-aminopyridine (0.75 mmol), cuprous iodide (0.15 mmol) and acetic acid (1.0 mmol), after stirring evenly, put it into a 120°C oil bath and continue stirring. TLC detection substrate 1a After disappearing, add 1ml of water, continue heating for 0.5 hour, and the reaction ends. The reaction solution was poured into water (15 mL), extracted with dichloromethane (3×15 mL), and the organic phases were combined. Backwash 3 times with 60 ml of water. The organic phase was dried with anhydrous magnesium sulfate, suction filtered, and then the organic solvent was distilled off under reduced pressure, and finally subjected to silica gel column chromatography to obtain a white solid 3a , confirmed to be imidazo[1,2-a]pyridine-3-carbaldehyde compound ...

Embodiment 2

[0025] Embodiment 2 imidazo[1,2-a]pyridine-3-carbaldehyde derivatives 3b preparation of

[0026] The 2-aminopyridine in "Example 1" was replaced by p-methoxycinnamaldehyde, the reaction steps were the same as in "Example 1", the reaction temperature was 110°C, and the reaction time was 4 hours.

[0027] The experimental results are shown in Table 1.

[0028]

[0029] Spectral analysis data 3b :

[0030] 1 H NMR (500 MHz, CDCl 3 ) δ 10.05 (s, 1H), 9.65 (d, J = 6.5 Hz, 1H), 7.80-7.77 (m, 3H), 7.59-7.55 (m, 1H), 7.11 (td, J = 7.0 Hz, J = 1.0 Hz, 1H), 7.07-7.05 (m, 2H), 3.89 (s, 3H); 13 C NMR (CDCl 3 , 125 Hz) δ 179.4, 160.9, 158.1, 147.6, 131.0, 130.3, 128.7, 124.6, 120.3, 117.1, 115.0, 114.2, 55.3; HRMS (ESI) m / z calculated for C 15 h13 N 2 o 2 [M+H] + : 253.0972, found 253.0974.

Embodiment 3

[0031] Example 3 imidazo[1,2-a]pyridine-3-carbaldehyde derivatives 3c preparation of

[0032] The 2-aminopyridine in "Example 1" was replaced with o-nitrocinnamaldehyde, the reaction steps were the same as in "Example 1", the reaction temperature was 140° C., and the reaction time was 5 hours. The experimental results are shown in Table 1.

[0033]

[0034] Spectral analysis data 3c :

[0035] 1 H NMR (500 MHz, CDCl 3 ) δ 9.81 (s, 1H), 9.61 (d, J = 7.0 Hz, 1H), 9.11 (d, J = 8.0 Hz, 1H), 7.80-7.74 (m, 2H), 7.70-7.60 (m, 3H), 7.20 (t, J = 7.0 Hz, 1H); 13 C NMR (CDCl 3 , 125 Hz) δ 177.9, 154.2, 149.6, 147.6, 133.0, 132.6, 130.7, 130.5, 128.6, 127.2, 124.9, 121.2, 117.7, 115.8; HRMS (ESI) m / z calculated for C 14 h 10 N 3 o 3 [M+H] + : 268.0717, found 268.0718.

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Abstract

The invention belongs to the technical field of the organic synthetic chemistry and specifically relates to a simple and feasible method for synthesizing an imidazo[1,2-a]pyridine-3-formaldehyde compound through one step. The invention provides a method for synthesizing the imidazo[1,2-a]pyridine-3-formaldehyde compound through a [3+2] cyclization reaction of 2-aminopyridine and cinnamylaldehyde through one step; the method has the advantages that the raw materials are simple and easily available, the step is simple and efficient, multi-step synthesis of a reaction precursor is avoided, the reaction time is effectively shortened, the extended application range of the product is wide, and the like. In particular, due to the use of 2-aminopyridine / pyrazine, imidazo[1,2-a]pyridine / pyrazine derivatives can be synthesized through one step. The method provided by the invention is applicable to synthesizing various imidazo[1,2-a]pyridine compounds. Besides, the method is capable of effectively synthesizing drug molecules Alpidem and Zolipidem.

Description

[0001] technical field [0002] The invention belongs to the technical field of organic synthesis chemistry, in particular to a simple and easy one-step synthesis of imidazo[1,2- a ] The method of pyridine-3-carboxaldehyde compounds. Background technique [0003] Imidazopyridine compounds are a very important class of nitrogen-containing fused heterocyclic compounds, which are widely used in synthesis, medicine, pesticide and dye industries. Common imidazopyridine compounds—imidazo[1, 2-a]pyridine derivatives are not only numerous in number, but also complex in structure. Derivatives based on imidazo[1,2-a]pyridine have attracted much attention due to their superior anti-tumor, anti-virus, sedative-hypnotic, anti-inflammatory and other biological activities, and many of them have become marketed drugs, such as Vasodilators Olprinone, sleeping pills Alpidem, Zolipidem, etc. The design and synthesis of imidazo[1, 2-a]pyridine derivatives and the research on the synthesis ...

Claims

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Application Information

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IPC IPC(8): C07D471/04C07D487/04
Inventor 毕锡和方桂春张林廖沛球
Owner NORTHEAST NORMAL UNIVERSITY
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