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Imidazo[1,2-a]pyridine A3-Coupling Catalyzed by a Cu/SiO2 Material

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In this work, we report the preparation of a copper-silica material (Cu/SiO2) by a sol-gel methodology and its characterization concerning composition and textural properties. The Cu/SiO2 material was successfully applied… Click to show full abstract

In this work, we report the preparation of a copper-silica material (Cu/SiO2) by a sol-gel methodology and its characterization concerning composition and textural properties. The Cu/SiO2 material was successfully applied as a Lewis acid heterogeneous catalyst for the A-coupling from 2-aminopyridine, aldehydes and alkynes to imidazo[1,2-a]pyridines (45-82%), which are relevant pharmacological scaffolds. The synthesis shows a number of advantages, such as easy separation from the reaction media and the minimal formation of metal aqueous wastes. Investigation of the mechanism supports the involvement of the formation of reaction intermediates inside the pores of the mesoporous material prior to 5-exo-dig cyclization.

Keywords: pyridine coupling; catalyzed sio2; coupling catalyzed; imidazo pyridine; sio2 material; material

Journal Title: Journal of the Brazilian Chemical Society
Year Published: 2019

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