A Comparative Study on the Groebke-Blackburn-Bienaymé Three-Component Reaction Catalyzed by Rare Earth Triflates under Microwave Heating
Autor(a) principal: | |
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Data de Publicação: | 2020 |
Outros Autores: | , , , , , |
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=S0103-50532020000701434 |
Resumo: | Over the last twenty years, the Groebke-Blackburn-Bienaymé (GBB) reaction has been emerged as a powerful tool to access different nitrogen-based heterocycles as privileged scaffolds in medicinal chemistry. This multicomponent reaction is usually catalyzed by ordinary Brønsted or Lewis acid catalysts. Herein, we present a comparative study on the catalytic efficiencies of different rare earth triflates in GBB reactions under microwave heating, involving 2-aminopyridine or 2-aminothiazole, as aminoazole component, and different aldehydes and aliphatic isocyanides. The use of gadolinium(III) triflate as cheaper alternative catalyst for the most commonly used scandium(III) triflate was acknowledged for the first time, and a library of twenty three imidazo[1,2-a]pyridines and imidazo[2,1-b]thiazoles could be obtained in good to excellent yields. |
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A Comparative Study on the Groebke-Blackburn-Bienaymé Three-Component Reaction Catalyzed by Rare Earth Triflates under Microwave HeatingGroebke-Blackburn-Bienaymécatalysisrare earth triflatemulticomponent reactiongadolinium(III) triflateOver the last twenty years, the Groebke-Blackburn-Bienaymé (GBB) reaction has been emerged as a powerful tool to access different nitrogen-based heterocycles as privileged scaffolds in medicinal chemistry. This multicomponent reaction is usually catalyzed by ordinary Brønsted or Lewis acid catalysts. Herein, we present a comparative study on the catalytic efficiencies of different rare earth triflates in GBB reactions under microwave heating, involving 2-aminopyridine or 2-aminothiazole, as aminoazole component, and different aldehydes and aliphatic isocyanides. The use of gadolinium(III) triflate as cheaper alternative catalyst for the most commonly used scandium(III) triflate was acknowledged for the first time, and a library of twenty three imidazo[1,2-a]pyridines and imidazo[2,1-b]thiazoles could be obtained in good to excellent yields.Sociedade Brasileira de Química2020-07-01info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersiontext/htmlhttp://old.scielo.br/scielo.php?script=sci_arttext&pid=S0103-50532020000701434Journal of the Brazilian Chemical Society v.31 n.7 2020reponame:Journal of the Brazilian Chemical Society (Online)instname:Sociedade Brasileira de Química (SBQ)instacron:SBQ10.21577/0103-5053.20200028info:eu-repo/semantics/openAccessSantos,Gabriela F. D.Anjos,Nicolas S.Gibeli,Miguel M.Silva,Guilherme A.Fernandes,Pâmela C. S.Fiorentino,Everton S. C.Longo Jr.,Luiz S.eng2020-06-30T00:00:00Zoai:scielo:S0103-50532020000701434Revistahttp://jbcs.sbq.org.brONGhttps://old.scielo.br/oai/scielo-oai.php||office@jbcs.sbq.org.br1678-47900103-5053opendoar:2020-06-30T00:00Journal of the Brazilian Chemical Society (Online) - Sociedade Brasileira de Química (SBQ)false |
dc.title.none.fl_str_mv |
A Comparative Study on the Groebke-Blackburn-Bienaymé Three-Component Reaction Catalyzed by Rare Earth Triflates under Microwave Heating |
title |
A Comparative Study on the Groebke-Blackburn-Bienaymé Three-Component Reaction Catalyzed by Rare Earth Triflates under Microwave Heating |
spellingShingle |
A Comparative Study on the Groebke-Blackburn-Bienaymé Three-Component Reaction Catalyzed by Rare Earth Triflates under Microwave Heating Santos,Gabriela F. D. Groebke-Blackburn-Bienaymé catalysis rare earth triflate multicomponent reaction gadolinium(III) triflate |
title_short |
A Comparative Study on the Groebke-Blackburn-Bienaymé Three-Component Reaction Catalyzed by Rare Earth Triflates under Microwave Heating |
title_full |
A Comparative Study on the Groebke-Blackburn-Bienaymé Three-Component Reaction Catalyzed by Rare Earth Triflates under Microwave Heating |
title_fullStr |
A Comparative Study on the Groebke-Blackburn-Bienaymé Three-Component Reaction Catalyzed by Rare Earth Triflates under Microwave Heating |
title_full_unstemmed |
A Comparative Study on the Groebke-Blackburn-Bienaymé Three-Component Reaction Catalyzed by Rare Earth Triflates under Microwave Heating |
title_sort |
A Comparative Study on the Groebke-Blackburn-Bienaymé Three-Component Reaction Catalyzed by Rare Earth Triflates under Microwave Heating |
author |
Santos,Gabriela F. D. |
author_facet |
Santos,Gabriela F. D. Anjos,Nicolas S. Gibeli,Miguel M. Silva,Guilherme A. Fernandes,Pâmela C. S. Fiorentino,Everton S. C. Longo Jr.,Luiz S. |
author_role |
author |
author2 |
Anjos,Nicolas S. Gibeli,Miguel M. Silva,Guilherme A. Fernandes,Pâmela C. S. Fiorentino,Everton S. C. Longo Jr.,Luiz S. |
author2_role |
author author author author author author |
dc.contributor.author.fl_str_mv |
Santos,Gabriela F. D. Anjos,Nicolas S. Gibeli,Miguel M. Silva,Guilherme A. Fernandes,Pâmela C. S. Fiorentino,Everton S. C. Longo Jr.,Luiz S. |
dc.subject.por.fl_str_mv |
Groebke-Blackburn-Bienaymé catalysis rare earth triflate multicomponent reaction gadolinium(III) triflate |
topic |
Groebke-Blackburn-Bienaymé catalysis rare earth triflate multicomponent reaction gadolinium(III) triflate |
description |
Over the last twenty years, the Groebke-Blackburn-Bienaymé (GBB) reaction has been emerged as a powerful tool to access different nitrogen-based heterocycles as privileged scaffolds in medicinal chemistry. This multicomponent reaction is usually catalyzed by ordinary Brønsted or Lewis acid catalysts. Herein, we present a comparative study on the catalytic efficiencies of different rare earth triflates in GBB reactions under microwave heating, involving 2-aminopyridine or 2-aminothiazole, as aminoazole component, and different aldehydes and aliphatic isocyanides. The use of gadolinium(III) triflate as cheaper alternative catalyst for the most commonly used scandium(III) triflate was acknowledged for the first time, and a library of twenty three imidazo[1,2-a]pyridines and imidazo[2,1-b]thiazoles could be obtained in good to excellent yields. |
publishDate |
2020 |
dc.date.none.fl_str_mv |
2020-07-01 |
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=S0103-50532020000701434 |
url |
http://old.scielo.br/scielo.php?script=sci_arttext&pid=S0103-50532020000701434 |
dc.language.iso.fl_str_mv |
eng |
language |
eng |
dc.relation.none.fl_str_mv |
10.21577/0103-5053.20200028 |
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.31 n.7 2020 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 |
_version_ |
1750318183073447936 |