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

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

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 A3-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.

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Main Authors: Salles,Helena D. de, Silva,Tiago L. da, Radatz,Cátia S., Affeldt,Ricardo F., Benvenutti,Edilson V., Schneider,Paulo H.
Format: Digital revista
Language:English
Published: Sociedade Brasileira de Química 2019
Online Access:http://old.scielo.br/scielo.php?script=sci_arttext&pid=S0103-50532019000901825
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spelling oai:scielo:S0103-505320190009018252019-09-11Imidazo[1,2-a]pyridine A3-Coupling Catalyzed by a Cu/SiO2 MaterialSalles,Helena D. deSilva,Tiago L. daRadatz,Cátia S.Affeldt,Ricardo F.Benvenutti,Edilson V.Schneider,Paulo H. imidazo[1,2-a]pyridines heterogeneous catalyst A3-coupling reaction 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 A3-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.info:eu-repo/semantics/openAccessSociedade Brasileira de QuímicaJournal of the Brazilian Chemical Society v.30 n.9 20192019-09-01info:eu-repo/semantics/articletext/htmlhttp://old.scielo.br/scielo.php?script=sci_arttext&pid=S0103-50532019000901825en10.21577/0103-5053.20190089
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country Brasil
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region America del Sur
libraryname SciELO
language English
format Digital
author Salles,Helena D. de
Silva,Tiago L. da
Radatz,Cátia S.
Affeldt,Ricardo F.
Benvenutti,Edilson V.
Schneider,Paulo H.
spellingShingle Salles,Helena D. de
Silva,Tiago L. da
Radatz,Cátia S.
Affeldt,Ricardo F.
Benvenutti,Edilson V.
Schneider,Paulo H.
Imidazo[1,2-a]pyridine A3-Coupling Catalyzed by a Cu/SiO2 Material
author_facet Salles,Helena D. de
Silva,Tiago L. da
Radatz,Cátia S.
Affeldt,Ricardo F.
Benvenutti,Edilson V.
Schneider,Paulo H.
author_sort Salles,Helena D. de
title Imidazo[1,2-a]pyridine A3-Coupling Catalyzed by a Cu/SiO2 Material
title_short Imidazo[1,2-a]pyridine A3-Coupling Catalyzed by a Cu/SiO2 Material
title_full Imidazo[1,2-a]pyridine A3-Coupling Catalyzed by a Cu/SiO2 Material
title_fullStr Imidazo[1,2-a]pyridine A3-Coupling Catalyzed by a Cu/SiO2 Material
title_full_unstemmed Imidazo[1,2-a]pyridine A3-Coupling Catalyzed by a Cu/SiO2 Material
title_sort imidazo[1,2-a]pyridine a3-coupling catalyzed by a cu/sio2 material
description 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 A3-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.
publisher Sociedade Brasileira de Química
publishDate 2019
url http://old.scielo.br/scielo.php?script=sci_arttext&pid=S0103-50532019000901825
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