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A kind of catalytic synthesis method of c-3 aryl selenoimidazopyridine compound

A technology of imidazopyridine and synthesis method, applied in the field of synthetic chemistry, can solve problems such as restricting large-scale industrial production of compounds, high temperature, and inability to recycle

Active Publication Date: 2021-08-20
QINGDAO UNIV OF SCI & TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0007] At present, the method of constructing C-3 aryl selenium substituted imidazopyridine compounds has been reported, but there are some disadvantages, such as higher temperature, use of high boiling point solvents, and use of copper salt catalysts that cannot be recycled. These methods limit Large-scale industrial production of such compounds

Method used

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  • A kind of catalytic synthesis method of c-3 aryl selenoimidazopyridine compound
  • A kind of catalytic synthesis method of c-3 aryl selenoimidazopyridine compound
  • A kind of catalytic synthesis method of c-3 aryl selenoimidazopyridine compound

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Experimental program
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Effect test

Embodiment 1

[0042]

[0043] At room temperature, nano copper ferrite (0.02 mmol), 2-phenylimidazo[1,2-a]pyridine (0.2 mmol ), diphenyldiselenide (0.12 mmol), and 2 mL of anhydrous tetrahydrofuran were added under oxygen, and the tube was stirred in an oil bath, and reacted at 40 ° C for 24 h. The progress of the reaction was monitored by TLC (Thin Layer Chromatography). After the reaction was complete, the resulting solution was cooled to room temperature. The magnet is placed outside the reaction vessel, the catalyst is adsorbed on the wall of the reaction vessel by magnetic attraction, the reaction solution is poured into a separatory funnel, and 5 milliliters of ethyl acetate is poured into the reaction vessel, and the catalyst is washed twice. Pour ethyl acetate into the separatory funnel, then add 5 milliliters of water and 5 milliliters of ethyl acetate to the separatory funnel, extract the reaction solution, repeat the extraction 4 times, combine the organic phases and dry them...

Embodiment 2

[0047]

[0048] At room temperature, nano copper ferrite (0.03 mmol), 2-phenylimidazo[1,2-a]pyridine (0.2 mmol ), p-chlorodiphenyldiselenide (0.12 mmol), 2 mL of anhydrous THF was added under oxygen, the tube was placed in an oil bath and stirred, and reacted at 60 ° C for 16 h. The progress of the reaction was monitored by TLC (Thin Layer Chromatography). After the reaction was complete, the resulting solution was cooled to room temperature. The magnet is placed outside the reaction vessel, the catalyst is adsorbed on the wall of the reaction vessel by magnetic attraction, the reaction solution is poured into a separatory funnel, and 5 milliliters of ethyl acetate is poured into the reaction vessel, and the catalyst is washed twice. Pour ethyl acetate into the separatory funnel, then add 5 milliliters of water and 5 milliliters of ethyl acetate to the separatory funnel, extract the reaction solution, repeat the extraction 4 times, combine the organic phases and dry them w...

Embodiment 3

[0053]

[0054] At room temperature, nanometer copper ferrite (0.01 mmol), 2-phenylimidazo[1,2-a]pyridine (0.2 mmol ), p-bromodiphenyldiselenide (0.15 mmol), 2 mL of anhydrous THF was added under oxygen, the tube was placed in an oil bath and stirred, and reacted at 60 ° C for 24 h. The progress of the reaction was monitored by TLC (Thin Layer Chromatography). After the reaction was complete, the resulting solution was cooled to room temperature. The magnet is placed outside the reaction vessel, the catalyst is adsorbed on the wall of the reaction vessel by magnetic attraction, the reaction solution is poured into a separatory funnel, and 5 milliliters of ethyl acetate is poured into the reaction vessel, and the catalyst is washed twice. Pour ethyl acetate into the separatory funnel, then add 5 milliliters of water and 5 milliliters of ethyl acetate to the separatory funnel, extract the reaction solution, repeat the extraction 4 times, combine the organic phases and dry th...

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Abstract

The invention provides a catalytic synthesis method of a C-3 aryl selenium substituted imidazopyridine compound, specifically: dissolving an imidazo[1,2-a]pyridine compound and a diaryl diselenide compound In an organic solvent, add a copper ferrite catalyst to catalyze and activate the C-3 C-H bond of imidazopyridine, and react to prepare a C-3 aryl selenium substituted imidazopyridine compound. No ligand is needed in the reaction, and no Alkali needs to be added, the catalyst can be recycled, the reaction cost is reduced, and the problem of metal residue in the target product can be minimized.

Description

technical field [0001] The invention belongs to the field of synthetic chemistry and relates to a catalytic synthesis method of C-3 aryl selenium substituted imidazopyridine compounds. Background technique [0002] Organoselenium compounds have special biological activity and fluorescent properties, and are widely used in the fields of pharmaceuticals and materials science, making scientists and researchers have a strong research interest in them. Some selenium-containing organic molecules reported in the literature have good pharmaceutical activity. As shown below, some representative molecules such as compounds I (antiproliferative agent), II (5-LOX (lipoxygenase inhibitor) and III (antineoplastic agent) have the following structural formulas: [0003] [0004] Therefore, finding a simple, efficient, and green method to construct selenium-containing compounds has attracted extensive attention of researchers. It is well known that the compounds containing imidazo[1,2-a...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D471/04
CPCC07D471/04Y02P20/584
Inventor 杨道山魏伟邢承雨
Owner QINGDAO UNIV OF SCI & TECH