Synthesis of N-Substituted Pyrroles Catalyzed by Low-Cost and Commercially Available Aluminas

Autores
Portilla Zúñiga, Omar Miguel; Bautista Aguilera, Óscar M.; Martínez, José J.; Rojas, Hugo; Macías, Mario A.; Iriepa, Isabel; Pérez Redondo, Adrián; Sathicq, Angel Gabriel; Castillo, Juan Carlos; Romanelli, Gustavo Pablo
Año de publicación
2023
Idioma
inglés
Tipo de recurso
artículo
Estado
versión publicada
Descripción
The Paal-Knorr reaction of acetonylacetone with primary amines catalyzed by CATAPAL 200 under conventional heating at 60 °C for 45 min afforded N-substituted pyrroles in 68?97% yields. The pyrrole 3g was studied by single-crystal and powder X-ray diffraction. The high percentage of Brønsted?Lewis acid sites (23%) and pore diameter (37.8 nm) of CATAPAL 200 favor the formation of the pyrrole ring because an increase in Brønsted acid sites efficiently catalyzes condensation and dehydration processes. This protocol is distinguished by its operational simplicity, high yields, reduced reaction time, no solvent required, stoichiometric amounts of reactants, low catalyst loading, and clean reaction profile. In addition, the CATAPAL 200 is cheap and commercially available leading to an efficient and lower-cost chemical transformation. The reusability of the catalyst for up to five cycles without appreciable loss of its catalytic activity makes the present protocol sustainable and advantageous compared to conventional methods.
Fil: Portilla Zúñiga, Omar Miguel. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - La Plata. Centro de Investigación y Desarrollo en Ciencias Aplicadas "Dr. Jorge J. Ronco". Universidad Nacional de la Plata. Facultad de Ciencias Exactas. Centro de Investigación y Desarrollo en Ciencias Aplicadas; Argentina
Fil: Bautista Aguilera, Óscar M.. Universidad de Alcalá; España
Fil: Martínez, José J.. Universidad Pedagógica y Tecnológica de Colombia; Colombia
Fil: Rojas, Hugo. Universidad Pedagógica y Tecnológica de Colombia; Colombia
Fil: Macías, Mario A.. Universidad de los Andes; Colombia
Fil: Iriepa, Isabel. Universidad de Alcalá; España
Fil: Pérez Redondo, Adrián. Universidad de Alcalá; España
Fil: Sathicq, Angel Gabriel. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - La Plata. Centro de Investigación y Desarrollo en Ciencias Aplicadas "Dr. Jorge J. Ronco". Universidad Nacional de la Plata. Facultad de Ciencias Exactas. Centro de Investigación y Desarrollo en Ciencias Aplicadas; Argentina
Fil: Castillo, Juan Carlos. Universidad Pedagógica y Tecnológica de Colombia; Colombia
Fil: Romanelli, Gustavo Pablo. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - La Plata. Centro de Investigación y Desarrollo en Ciencias Aplicadas "Dr. Jorge J. Ronco". Universidad Nacional de la Plata. Facultad de Ciencias Exactas. Centro de Investigación y Desarrollo en Ciencias Aplicadas; Argentina
Materia
ALUMINAS
GREEN CHEMISTRY
HETEROGENEOUS CATALYSIS
PAAL-KNORR REACTION
PYRROLES
X-RAY CRYSTALLOGRAPHY
Nivel de accesibilidad
acceso abierto
Condiciones de uso
https://creativecommons.org/licenses/by/2.5/ar/
Repositorio
CONICET Digital (CONICET)
Institución
Consejo Nacional de Investigaciones Científicas y Técnicas
OAI Identificador
oai:ri.conicet.gov.ar:11336/232149
Acceder
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oai_identifier_str oai:ri.conicet.gov.ar:11336/232149
network_acronym_str CONICETDig
repository_id_str 3498
network_name_str CONICET Digital (CONICET)
spelling Synthesis of N-Substituted Pyrroles Catalyzed by Low-Cost and Commercially Available AluminasPortilla Zúñiga, Omar MiguelBautista Aguilera, Óscar M.Martínez, José J.Rojas, HugoMacías, Mario A.Iriepa, IsabelPérez Redondo, AdriánSathicq, Angel GabrielCastillo, Juan CarlosRomanelli, Gustavo PabloALUMINASGREEN CHEMISTRYHETEROGENEOUS CATALYSISPAAL-KNORR REACTIONPYRROLESX-RAY CRYSTALLOGRAPHYhttps://purl.org/becyt/ford/2.4https://purl.org/becyt/ford/2The Paal-Knorr reaction of acetonylacetone with primary amines catalyzed by CATAPAL 200 under conventional heating at 60 °C for 45 min afforded N-substituted pyrroles in 68?97% yields. The pyrrole 3g was studied by single-crystal and powder X-ray diffraction. The high percentage of Brønsted?Lewis acid sites (23%) and pore diameter (37.8 nm) of CATAPAL 200 favor the formation of the pyrrole ring because an increase in Brønsted acid sites efficiently catalyzes condensation and dehydration processes. This protocol is distinguished by its operational simplicity, high yields, reduced reaction time, no solvent required, stoichiometric amounts of reactants, low catalyst loading, and clean reaction profile. In addition, the CATAPAL 200 is cheap and commercially available leading to an efficient and lower-cost chemical transformation. The reusability of the catalyst for up to five cycles without appreciable loss of its catalytic activity makes the present protocol sustainable and advantageous compared to conventional methods.Fil: Portilla Zúñiga, Omar Miguel. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - La Plata. Centro de Investigación y Desarrollo en Ciencias Aplicadas "Dr. Jorge J. Ronco". Universidad Nacional de la Plata. Facultad de Ciencias Exactas. Centro de Investigación y Desarrollo en Ciencias Aplicadas; ArgentinaFil: Bautista Aguilera, Óscar M.. Universidad de Alcalá; EspañaFil: Martínez, José J.. Universidad Pedagógica y Tecnológica de Colombia; ColombiaFil: Rojas, Hugo. Universidad Pedagógica y Tecnológica de Colombia; ColombiaFil: Macías, Mario A.. Universidad de los Andes; ColombiaFil: Iriepa, Isabel. Universidad de Alcalá; EspañaFil: Pérez Redondo, Adrián. Universidad de Alcalá; EspañaFil: Sathicq, Angel Gabriel. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - La Plata. Centro de Investigación y Desarrollo en Ciencias Aplicadas "Dr. Jorge J. Ronco". Universidad Nacional de la Plata. Facultad de Ciencias Exactas. Centro de Investigación y Desarrollo en Ciencias Aplicadas; ArgentinaFil: Castillo, Juan Carlos. Universidad Pedagógica y Tecnológica de Colombia; ColombiaFil: Romanelli, Gustavo Pablo. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - La Plata. Centro de Investigación y Desarrollo en Ciencias Aplicadas "Dr. Jorge J. Ronco". Universidad Nacional de la Plata. Facultad de Ciencias Exactas. Centro de Investigación y Desarrollo en Ciencias Aplicadas; ArgentinaMDPI2023-03info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionhttp://purl.org/coar/resource_type/c_6501info:ar-repo/semantics/articuloapplication/pdfapplication/pdfapplication/pdfhttp://hdl.handle.net/11336/232149Portilla Zúñiga, Omar Miguel; Bautista Aguilera, Óscar M.; Martínez, José J.; Rojas, Hugo; Macías, Mario A.; et al.; Synthesis of N-Substituted Pyrroles Catalyzed by Low-Cost and Commercially Available Aluminas; MDPI; Catalysts; 13; 3; 3-2023; 1-172073-4344CONICET DigitalCONICETenginfo:eu-repo/semantics/altIdentifier/doi/10.3390/catal13030603info:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2025-09-29T09:33:48Zoai:ri.conicet.gov.ar:11336/232149instacron:CONICETInstitucionalhttp://ri.conicet.gov.ar/Organismo científico-tecnológicoNo correspondehttp://ri.conicet.gov.ar/oai/requestdasensio@conicet.gov.ar; lcarlino@conicet.gov.arArgentinaNo correspondeNo correspondeNo correspondeopendoar:34982025-09-29 09:33:48.757CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse
dc.title.none.fl_str_mv Synthesis of N-Substituted Pyrroles Catalyzed by Low-Cost and Commercially Available Aluminas
title Synthesis of N-Substituted Pyrroles Catalyzed by Low-Cost and Commercially Available Aluminas
spellingShingle Synthesis of N-Substituted Pyrroles Catalyzed by Low-Cost and Commercially Available Aluminas
Portilla Zúñiga, Omar Miguel
ALUMINAS
GREEN CHEMISTRY
HETEROGENEOUS CATALYSIS
PAAL-KNORR REACTION
PYRROLES
X-RAY CRYSTALLOGRAPHY
title_short Synthesis of N-Substituted Pyrroles Catalyzed by Low-Cost and Commercially Available Aluminas
title_full Synthesis of N-Substituted Pyrroles Catalyzed by Low-Cost and Commercially Available Aluminas
title_fullStr Synthesis of N-Substituted Pyrroles Catalyzed by Low-Cost and Commercially Available Aluminas
title_full_unstemmed Synthesis of N-Substituted Pyrroles Catalyzed by Low-Cost and Commercially Available Aluminas
title_sort Synthesis of N-Substituted Pyrroles Catalyzed by Low-Cost and Commercially Available Aluminas
dc.creator.none.fl_str_mv Portilla Zúñiga, Omar Miguel
Bautista Aguilera, Óscar M.
Martínez, José J.
Rojas, Hugo
Macías, Mario A.
Iriepa, Isabel
Pérez Redondo, Adrián
Sathicq, Angel Gabriel
Castillo, Juan Carlos
Romanelli, Gustavo Pablo
author Portilla Zúñiga, Omar Miguel
author_facet Portilla Zúñiga, Omar Miguel
Bautista Aguilera, Óscar M.
Martínez, José J.
Rojas, Hugo
Macías, Mario A.
Iriepa, Isabel
Pérez Redondo, Adrián
Sathicq, Angel Gabriel
Castillo, Juan Carlos
Romanelli, Gustavo Pablo
author_role author
author2 Bautista Aguilera, Óscar M.
Martínez, José J.
Rojas, Hugo
Macías, Mario A.
Iriepa, Isabel
Pérez Redondo, Adrián
Sathicq, Angel Gabriel
Castillo, Juan Carlos
Romanelli, Gustavo Pablo
author2_role author
author
author
author
author
author
author
author
author
dc.subject.none.fl_str_mv ALUMINAS
GREEN CHEMISTRY
HETEROGENEOUS CATALYSIS
PAAL-KNORR REACTION
PYRROLES
X-RAY CRYSTALLOGRAPHY
topic ALUMINAS
GREEN CHEMISTRY
HETEROGENEOUS CATALYSIS
PAAL-KNORR REACTION
PYRROLES
X-RAY CRYSTALLOGRAPHY
purl_subject.fl_str_mv https://purl.org/becyt/ford/2.4
https://purl.org/becyt/ford/2
dc.description.none.fl_txt_mv The Paal-Knorr reaction of acetonylacetone with primary amines catalyzed by CATAPAL 200 under conventional heating at 60 °C for 45 min afforded N-substituted pyrroles in 68?97% yields. The pyrrole 3g was studied by single-crystal and powder X-ray diffraction. The high percentage of Brønsted?Lewis acid sites (23%) and pore diameter (37.8 nm) of CATAPAL 200 favor the formation of the pyrrole ring because an increase in Brønsted acid sites efficiently catalyzes condensation and dehydration processes. This protocol is distinguished by its operational simplicity, high yields, reduced reaction time, no solvent required, stoichiometric amounts of reactants, low catalyst loading, and clean reaction profile. In addition, the CATAPAL 200 is cheap and commercially available leading to an efficient and lower-cost chemical transformation. The reusability of the catalyst for up to five cycles without appreciable loss of its catalytic activity makes the present protocol sustainable and advantageous compared to conventional methods.
Fil: Portilla Zúñiga, Omar Miguel. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - La Plata. Centro de Investigación y Desarrollo en Ciencias Aplicadas "Dr. Jorge J. Ronco". Universidad Nacional de la Plata. Facultad de Ciencias Exactas. Centro de Investigación y Desarrollo en Ciencias Aplicadas; Argentina
Fil: Bautista Aguilera, Óscar M.. Universidad de Alcalá; España
Fil: Martínez, José J.. Universidad Pedagógica y Tecnológica de Colombia; Colombia
Fil: Rojas, Hugo. Universidad Pedagógica y Tecnológica de Colombia; Colombia
Fil: Macías, Mario A.. Universidad de los Andes; Colombia
Fil: Iriepa, Isabel. Universidad de Alcalá; España
Fil: Pérez Redondo, Adrián. Universidad de Alcalá; España
Fil: Sathicq, Angel Gabriel. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - La Plata. Centro de Investigación y Desarrollo en Ciencias Aplicadas "Dr. Jorge J. Ronco". Universidad Nacional de la Plata. Facultad de Ciencias Exactas. Centro de Investigación y Desarrollo en Ciencias Aplicadas; Argentina
Fil: Castillo, Juan Carlos. Universidad Pedagógica y Tecnológica de Colombia; Colombia
Fil: Romanelli, Gustavo Pablo. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - La Plata. Centro de Investigación y Desarrollo en Ciencias Aplicadas "Dr. Jorge J. Ronco". Universidad Nacional de la Plata. Facultad de Ciencias Exactas. Centro de Investigación y Desarrollo en Ciencias Aplicadas; Argentina
description The Paal-Knorr reaction of acetonylacetone with primary amines catalyzed by CATAPAL 200 under conventional heating at 60 °C for 45 min afforded N-substituted pyrroles in 68?97% yields. The pyrrole 3g was studied by single-crystal and powder X-ray diffraction. The high percentage of Brønsted?Lewis acid sites (23%) and pore diameter (37.8 nm) of CATAPAL 200 favor the formation of the pyrrole ring because an increase in Brønsted acid sites efficiently catalyzes condensation and dehydration processes. This protocol is distinguished by its operational simplicity, high yields, reduced reaction time, no solvent required, stoichiometric amounts of reactants, low catalyst loading, and clean reaction profile. In addition, the CATAPAL 200 is cheap and commercially available leading to an efficient and lower-cost chemical transformation. The reusability of the catalyst for up to five cycles without appreciable loss of its catalytic activity makes the present protocol sustainable and advantageous compared to conventional methods.
publishDate 2023
dc.date.none.fl_str_mv 2023-03
dc.type.none.fl_str_mv info:eu-repo/semantics/article
info:eu-repo/semantics/publishedVersion
http://purl.org/coar/resource_type/c_6501
info:ar-repo/semantics/articulo
format article
status_str publishedVersion
dc.identifier.none.fl_str_mv http://hdl.handle.net/11336/232149
Portilla Zúñiga, Omar Miguel; Bautista Aguilera, Óscar M.; Martínez, José J.; Rojas, Hugo; Macías, Mario A.; et al.; Synthesis of N-Substituted Pyrroles Catalyzed by Low-Cost and Commercially Available Aluminas; MDPI; Catalysts; 13; 3; 3-2023; 1-17
2073-4344
CONICET Digital
CONICET
url http://hdl.handle.net/11336/232149
identifier_str_mv Portilla Zúñiga, Omar Miguel; Bautista Aguilera, Óscar M.; Martínez, José J.; Rojas, Hugo; Macías, Mario A.; et al.; Synthesis of N-Substituted Pyrroles Catalyzed by Low-Cost and Commercially Available Aluminas; MDPI; Catalysts; 13; 3; 3-2023; 1-17
2073-4344
CONICET Digital
CONICET
dc.language.none.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv info:eu-repo/semantics/altIdentifier/doi/10.3390/catal13030603
dc.rights.none.fl_str_mv info:eu-repo/semantics/openAccess
https://creativecommons.org/licenses/by/2.5/ar/
eu_rights_str_mv openAccess
rights_invalid_str_mv https://creativecommons.org/licenses/by/2.5/ar/
dc.format.none.fl_str_mv application/pdf
application/pdf
application/pdf
dc.publisher.none.fl_str_mv MDPI
publisher.none.fl_str_mv MDPI
dc.source.none.fl_str_mv reponame:CONICET Digital (CONICET)
instname:Consejo Nacional de Investigaciones Científicas y Técnicas
reponame_str CONICET Digital (CONICET)
collection CONICET Digital (CONICET)
instname_str Consejo Nacional de Investigaciones Científicas y Técnicas
repository.name.fl_str_mv CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicas
repository.mail.fl_str_mv dasensio@conicet.gov.ar; lcarlino@conicet.gov.ar
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score 13.070432

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