A Comparative Study on the Groebke-Blackburn-Bienaymé Three-Component Reaction Catalyzed by Rare Earth Triflates under Microwave Heating

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.

Saved in:
Bibliographic Details
Main Authors: 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.
Format: Digital revista
Language:English
Published: Sociedade Brasileira de Química 2020
Online Access:http://old.scielo.br/scielo.php?script=sci_arttext&pid=S0103-50532020000701434
Tags: Add Tag
No Tags, Be the first to tag this record!
id oai:scielo:S0103-50532020000701434
record_format ojs
spelling oai:scielo:S0103-505320200007014342020-06-30A Comparative Study on the Groebke-Blackburn-Bienaymé Three-Component Reaction Catalyzed by Rare Earth Triflates under Microwave HeatingSantos,Gabriela F. D.Anjos,Nicolas S.Gibeli,Miguel M.Silva,Guilherme A.Fernandes,Pâmela C. S.Fiorentino,Everton S. C.Longo Jr.,Luiz S. Groebke-Blackburn-Bienaymé catalysis rare earth triflate multicomponent reaction gadolinium(III) triflate 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.info:eu-repo/semantics/openAccessSociedade Brasileira de QuímicaJournal of the Brazilian Chemical Society v.31 n.7 20202020-07-01info:eu-repo/semantics/articletext/htmlhttp://old.scielo.br/scielo.php?script=sci_arttext&pid=S0103-50532020000701434en10.21577/0103-5053.20200028
institution SCIELO
collection OJS
country Brasil
countrycode BR
component Revista
access En linea
databasecode rev-scielo-br
tag revista
region America del Sur
libraryname SciELO
language English
format Digital
author 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.
spellingShingle 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.
A Comparative Study on the Groebke-Blackburn-Bienaymé Three-Component Reaction Catalyzed by Rare Earth Triflates under Microwave Heating
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_sort Santos,Gabriela F. D.
title A Comparative Study on the Groebke-Blackburn-Bienaymé Three-Component Reaction Catalyzed by Rare Earth Triflates under Microwave Heating
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 comparative study on the groebke-blackburn-bienaymé three-component reaction catalyzed by rare earth triflates under microwave heating
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.
publisher Sociedade Brasileira de Química
publishDate 2020
url http://old.scielo.br/scielo.php?script=sci_arttext&pid=S0103-50532020000701434
work_keys_str_mv AT santosgabrielafd acomparativestudyonthegroebkeblackburnbienaymethreecomponentreactioncatalyzedbyrareearthtriflatesundermicrowaveheating
AT anjosnicolass acomparativestudyonthegroebkeblackburnbienaymethreecomponentreactioncatalyzedbyrareearthtriflatesundermicrowaveheating
AT gibelimiguelm acomparativestudyonthegroebkeblackburnbienaymethreecomponentreactioncatalyzedbyrareearthtriflatesundermicrowaveheating
AT silvaguilhermea acomparativestudyonthegroebkeblackburnbienaymethreecomponentreactioncatalyzedbyrareearthtriflatesundermicrowaveheating
AT fernandespamelacs acomparativestudyonthegroebkeblackburnbienaymethreecomponentreactioncatalyzedbyrareearthtriflatesundermicrowaveheating
AT fiorentinoevertonsc acomparativestudyonthegroebkeblackburnbienaymethreecomponentreactioncatalyzedbyrareearthtriflatesundermicrowaveheating
AT longojrluizs acomparativestudyonthegroebkeblackburnbienaymethreecomponentreactioncatalyzedbyrareearthtriflatesundermicrowaveheating
AT santosgabrielafd comparativestudyonthegroebkeblackburnbienaymethreecomponentreactioncatalyzedbyrareearthtriflatesundermicrowaveheating
AT anjosnicolass comparativestudyonthegroebkeblackburnbienaymethreecomponentreactioncatalyzedbyrareearthtriflatesundermicrowaveheating
AT gibelimiguelm comparativestudyonthegroebkeblackburnbienaymethreecomponentreactioncatalyzedbyrareearthtriflatesundermicrowaveheating
AT silvaguilhermea comparativestudyonthegroebkeblackburnbienaymethreecomponentreactioncatalyzedbyrareearthtriflatesundermicrowaveheating
AT fernandespamelacs comparativestudyonthegroebkeblackburnbienaymethreecomponentreactioncatalyzedbyrareearthtriflatesundermicrowaveheating
AT fiorentinoevertonsc comparativestudyonthegroebkeblackburnbienaymethreecomponentreactioncatalyzedbyrareearthtriflatesundermicrowaveheating
AT longojrluizs comparativestudyonthegroebkeblackburnbienaymethreecomponentreactioncatalyzedbyrareearthtriflatesundermicrowaveheating
_version_ 1756403810254716928