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

Detalhes bibliográficos
Autor(a) principal: Salles,Helena D. de
Data de Publicação: 2019
Outros Autores: Silva,Tiago L. da, Radatz,Cátia S., Affeldt,Ricardo F., Benvenutti,Edilson V., Schneider,Paulo H.
Tipo de documento: Artigo
Idioma: eng
Título da fonte: Journal of the Brazilian Chemical Society (Online)
Texto Completo: http://old.scielo.br/scielo.php?script=sci_arttext&pid=S0103-50532019000901825
Resumo: 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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spelling Imidazo[1,2-a]pyridine A3-Coupling Catalyzed by a Cu/SiO2 Materialimidazo[1,2-a]pyridinesheterogeneous catalystA3-coupling reactionIn 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.Sociedade Brasileira de Química2019-09-01info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersiontext/htmlhttp://old.scielo.br/scielo.php?script=sci_arttext&pid=S0103-50532019000901825Journal of the Brazilian Chemical Society v.30 n.9 2019reponame:Journal of the Brazilian Chemical Society (Online)instname:Sociedade Brasileira de Química (SBQ)instacron:SBQ10.21577/0103-5053.20190089info:eu-repo/semantics/openAccessSalles,Helena D. deSilva,Tiago L. daRadatz,Cátia S.Affeldt,Ricardo F.Benvenutti,Edilson V.Schneider,Paulo H.eng2019-09-11T00:00:00Zoai:scielo:S0103-50532019000901825Revistahttp://jbcs.sbq.org.brONGhttps://old.scielo.br/oai/scielo-oai.php||office@jbcs.sbq.org.br1678-47900103-5053opendoar:2019-09-11T00:00Journal of the Brazilian Chemical Society (Online) - Sociedade Brasileira de Química (SBQ)false
dc.title.none.fl_str_mv Imidazo[1,2-a]pyridine A3-Coupling Catalyzed by a Cu/SiO2 Material
title Imidazo[1,2-a]pyridine A3-Coupling Catalyzed by a Cu/SiO2 Material
spellingShingle Imidazo[1,2-a]pyridine A3-Coupling Catalyzed by a Cu/SiO2 Material
Salles,Helena D. de
imidazo[1,2-a]pyridines
heterogeneous catalyst
A3-coupling reaction
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
author Salles,Helena D. de
author_facet Salles,Helena D. de
Silva,Tiago L. da
Radatz,Cátia S.
Affeldt,Ricardo F.
Benvenutti,Edilson V.
Schneider,Paulo H.
author_role author
author2 Silva,Tiago L. da
Radatz,Cátia S.
Affeldt,Ricardo F.
Benvenutti,Edilson V.
Schneider,Paulo H.
author2_role author
author
author
author
author
dc.contributor.author.fl_str_mv Salles,Helena D. de
Silva,Tiago L. da
Radatz,Cátia S.
Affeldt,Ricardo F.
Benvenutti,Edilson V.
Schneider,Paulo H.
dc.subject.por.fl_str_mv imidazo[1,2-a]pyridines
heterogeneous catalyst
A3-coupling reaction
topic imidazo[1,2-a]pyridines
heterogeneous catalyst
A3-coupling reaction
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.
publishDate 2019
dc.date.none.fl_str_mv 2019-09-01
dc.type.driver.fl_str_mv info:eu-repo/semantics/article
dc.type.status.fl_str_mv info:eu-repo/semantics/publishedVersion
format article
status_str publishedVersion
dc.identifier.uri.fl_str_mv http://old.scielo.br/scielo.php?script=sci_arttext&pid=S0103-50532019000901825
url http://old.scielo.br/scielo.php?script=sci_arttext&pid=S0103-50532019000901825
dc.language.iso.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv 10.21577/0103-5053.20190089
dc.rights.driver.fl_str_mv info:eu-repo/semantics/openAccess
eu_rights_str_mv openAccess
dc.format.none.fl_str_mv text/html
dc.publisher.none.fl_str_mv Sociedade Brasileira de Química
publisher.none.fl_str_mv Sociedade Brasileira de Química
dc.source.none.fl_str_mv Journal of the Brazilian Chemical Society v.30 n.9 2019
reponame:Journal of the Brazilian Chemical Society (Online)
instname:Sociedade Brasileira de Química (SBQ)
instacron:SBQ
instname_str Sociedade Brasileira de Química (SBQ)
instacron_str SBQ
institution SBQ
reponame_str Journal of the Brazilian Chemical Society (Online)
collection Journal of the Brazilian Chemical Society (Online)
repository.name.fl_str_mv Journal of the Brazilian Chemical Society (Online) - Sociedade Brasileira de Química (SBQ)
repository.mail.fl_str_mv ||office@jbcs.sbq.org.br
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