A suitable synthesis of azlactones (4-benzylidene-2-phenyloxazolin-5-ones and 4-alkylidene-2-phenyloxazolin-5-ones) catalyzed by silica-alumina supported heteropolyacids

Autores
Romanelli, Gustavo Pablo; Autino, Juan Carlos; Vázquez, P.; Pizzio, Luis Rene; Blanco, Mirta Noemi; Caceres, Carmen Victoria
Año de publicación
2009
Idioma
inglés
Tipo de recurso
artículo
Estado
versión publicada
Descripción
Eleven examples of azlactones (4-benzylidene-2-phenyloxazolin-5-ones and 4-alkylidene-2-phenyloxazolin-5-ones) were prepared via an Erlenmeyer-type synthesis from aromatic aldehydes, hippuric acid and acetic anhydride was added to the hot solution as a dehydrating agent. Molybdophosphoric or tungstophosphoric acids supported on silica-alumina, obtained by the sol-gel method, catalyze the reaction. The prepared catalysts were characterized by X-ray diffraction and diffuse reflectance spectroscopy. The specific surface area of the catalysts was determined by the nitrogen adsorption/desorption at 196 °C technique, and the catalyst acidity was measured by potentiometric titration with n-butylamine. The heteropolyacid amount removed from the catalysts during the leaching with toluene was lower than 1%. The products were obtained with high conversion and selectivity. The yields were in the 87-96% range for the majority of the selected samples, with the exception of the azlactones synthesized from 2-nitrobenzaldehyde and cyclohexanone, which gave yields in the 70-80% range. The same catalysts were used several times without appreciable loss of their catalytic activity. A rational mechanism for the azlactone formation catalyzed by the supported heteropolyacid is proposed. © 2008 Elsevier B.V. All rights reserved.
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
Fil: Autino, Juan Carlos. Universidad Nacional de La Plata. Facultad de Ciencias Agrarias y Forestales. Departamento de Ciencias Exactas. Cátedra de Química Orgánica; Argentina
Fil: Vázquez, P.. 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: Pizzio, Luis Rene. 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: Blanco, Mirta Noemi. 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: Caceres, Carmen Victoria. 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
Azlactones
Catalysis
Condensation
Cyclodehydration
Keggin Heteropolyacids
Oxazolones
Nivel de accesibilidad
acceso abierto
Condiciones de uso
https://creativecommons.org/licenses/by-nc-sa/2.5/ar/
Repositorio
CONICET Digital (CONICET)
Institución
Consejo Nacional de Investigaciones Científicas y Técnicas
OAI Identificador
oai:ri.conicet.gov.ar:11336/54059
Acceder
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network_acronym_str CONICETDig
repository_id_str 3498
network_name_str CONICET Digital (CONICET)
spelling A suitable synthesis of azlactones (4-benzylidene-2-phenyloxazolin-5-ones and 4-alkylidene-2-phenyloxazolin-5-ones) catalyzed by silica-alumina supported heteropolyacidsRomanelli, Gustavo PabloAutino, Juan CarlosVázquez, P.Pizzio, Luis ReneBlanco, Mirta NoemiCaceres, Carmen VictoriaAzlactonesCatalysisCondensationCyclodehydrationKeggin HeteropolyacidsOxazoloneshttps://purl.org/becyt/ford/1.4https://purl.org/becyt/ford/1Eleven examples of azlactones (4-benzylidene-2-phenyloxazolin-5-ones and 4-alkylidene-2-phenyloxazolin-5-ones) were prepared via an Erlenmeyer-type synthesis from aromatic aldehydes, hippuric acid and acetic anhydride was added to the hot solution as a dehydrating agent. Molybdophosphoric or tungstophosphoric acids supported on silica-alumina, obtained by the sol-gel method, catalyze the reaction. The prepared catalysts were characterized by X-ray diffraction and diffuse reflectance spectroscopy. The specific surface area of the catalysts was determined by the nitrogen adsorption/desorption at 196 °C technique, and the catalyst acidity was measured by potentiometric titration with n-butylamine. The heteropolyacid amount removed from the catalysts during the leaching with toluene was lower than 1%. The products were obtained with high conversion and selectivity. The yields were in the 87-96% range for the majority of the selected samples, with the exception of the azlactones synthesized from 2-nitrobenzaldehyde and cyclohexanone, which gave yields in the 70-80% range. The same catalysts were used several times without appreciable loss of their catalytic activity. A rational mechanism for the azlactone formation catalyzed by the supported heteropolyacid is proposed. © 2008 Elsevier B.V. All rights reserved.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; ArgentinaFil: Autino, Juan Carlos. Universidad Nacional de La Plata. Facultad de Ciencias Agrarias y Forestales. Departamento de Ciencias Exactas. Cátedra de Química Orgánica; ArgentinaFil: Vázquez, P.. 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: Pizzio, Luis Rene. 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: Blanco, Mirta Noemi. 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: Caceres, Carmen Victoria. 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; ArgentinaElsevier Science2009-01info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionhttp://purl.org/coar/resource_type/c_6501info:ar-repo/semantics/articuloapplication/pdfapplication/pdfapplication/pdfapplication/pdfapplication/pdfapplication/pdfhttp://hdl.handle.net/11336/54059Romanelli, Gustavo Pablo; Autino, Juan Carlos; Vázquez, P.; Pizzio, Luis Rene; Blanco, Mirta Noemi; et al.; A suitable synthesis of azlactones (4-benzylidene-2-phenyloxazolin-5-ones and 4-alkylidene-2-phenyloxazolin-5-ones) catalyzed by silica-alumina supported heteropolyacids; Elsevier Science; Applied Catalysis A: General; 352; 1-2; 1-2009; 208-2130926-860XCONICET DigitalCONICETenginfo:eu-repo/semantics/altIdentifier/doi/10.1016/j.apcata.2008.10.003info:eu-repo/semantics/altIdentifier/url/https://www.sciencedirect.com/science/article/pii/S0926860X08006273info:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by-nc-sa/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2025-09-29T09:45:06Zoai:ri.conicet.gov.ar:11336/54059instacron: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 09:45:06.57CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse
dc.title.none.fl_str_mv A suitable synthesis of azlactones (4-benzylidene-2-phenyloxazolin-5-ones and 4-alkylidene-2-phenyloxazolin-5-ones) catalyzed by silica-alumina supported heteropolyacids
title A suitable synthesis of azlactones (4-benzylidene-2-phenyloxazolin-5-ones and 4-alkylidene-2-phenyloxazolin-5-ones) catalyzed by silica-alumina supported heteropolyacids
spellingShingle A suitable synthesis of azlactones (4-benzylidene-2-phenyloxazolin-5-ones and 4-alkylidene-2-phenyloxazolin-5-ones) catalyzed by silica-alumina supported heteropolyacids
Romanelli, Gustavo Pablo
Azlactones
Catalysis
Condensation
Cyclodehydration
Keggin Heteropolyacids
Oxazolones
title_short A suitable synthesis of azlactones (4-benzylidene-2-phenyloxazolin-5-ones and 4-alkylidene-2-phenyloxazolin-5-ones) catalyzed by silica-alumina supported heteropolyacids
title_full A suitable synthesis of azlactones (4-benzylidene-2-phenyloxazolin-5-ones and 4-alkylidene-2-phenyloxazolin-5-ones) catalyzed by silica-alumina supported heteropolyacids
title_fullStr A suitable synthesis of azlactones (4-benzylidene-2-phenyloxazolin-5-ones and 4-alkylidene-2-phenyloxazolin-5-ones) catalyzed by silica-alumina supported heteropolyacids
title_full_unstemmed A suitable synthesis of azlactones (4-benzylidene-2-phenyloxazolin-5-ones and 4-alkylidene-2-phenyloxazolin-5-ones) catalyzed by silica-alumina supported heteropolyacids
title_sort A suitable synthesis of azlactones (4-benzylidene-2-phenyloxazolin-5-ones and 4-alkylidene-2-phenyloxazolin-5-ones) catalyzed by silica-alumina supported heteropolyacids
dc.creator.none.fl_str_mv Romanelli, Gustavo Pablo
Autino, Juan Carlos
Vázquez, P.
Pizzio, Luis Rene
Blanco, Mirta Noemi
Caceres, Carmen Victoria
author Romanelli, Gustavo Pablo
author_facet Romanelli, Gustavo Pablo
Autino, Juan Carlos
Vázquez, P.
Pizzio, Luis Rene
Blanco, Mirta Noemi
Caceres, Carmen Victoria
author_role author
author2 Autino, Juan Carlos
Vázquez, P.
Pizzio, Luis Rene
Blanco, Mirta Noemi
Caceres, Carmen Victoria
author2_role author
author
author
author
author
dc.subject.none.fl_str_mv Azlactones
Catalysis
Condensation
Cyclodehydration
Keggin Heteropolyacids
Oxazolones
topic Azlactones
Catalysis
Condensation
Cyclodehydration
Keggin Heteropolyacids
Oxazolones
purl_subject.fl_str_mv https://purl.org/becyt/ford/1.4
https://purl.org/becyt/ford/1
dc.description.none.fl_txt_mv Eleven examples of azlactones (4-benzylidene-2-phenyloxazolin-5-ones and 4-alkylidene-2-phenyloxazolin-5-ones) were prepared via an Erlenmeyer-type synthesis from aromatic aldehydes, hippuric acid and acetic anhydride was added to the hot solution as a dehydrating agent. Molybdophosphoric or tungstophosphoric acids supported on silica-alumina, obtained by the sol-gel method, catalyze the reaction. The prepared catalysts were characterized by X-ray diffraction and diffuse reflectance spectroscopy. The specific surface area of the catalysts was determined by the nitrogen adsorption/desorption at 196 °C technique, and the catalyst acidity was measured by potentiometric titration with n-butylamine. The heteropolyacid amount removed from the catalysts during the leaching with toluene was lower than 1%. The products were obtained with high conversion and selectivity. The yields were in the 87-96% range for the majority of the selected samples, with the exception of the azlactones synthesized from 2-nitrobenzaldehyde and cyclohexanone, which gave yields in the 70-80% range. The same catalysts were used several times without appreciable loss of their catalytic activity. A rational mechanism for the azlactone formation catalyzed by the supported heteropolyacid is proposed. © 2008 Elsevier B.V. All rights reserved.
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
Fil: Autino, Juan Carlos. Universidad Nacional de La Plata. Facultad de Ciencias Agrarias y Forestales. Departamento de Ciencias Exactas. Cátedra de Química Orgánica; Argentina
Fil: Vázquez, P.. 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: Pizzio, Luis Rene. 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: Blanco, Mirta Noemi. 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: Caceres, Carmen Victoria. 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 Eleven examples of azlactones (4-benzylidene-2-phenyloxazolin-5-ones and 4-alkylidene-2-phenyloxazolin-5-ones) were prepared via an Erlenmeyer-type synthesis from aromatic aldehydes, hippuric acid and acetic anhydride was added to the hot solution as a dehydrating agent. Molybdophosphoric or tungstophosphoric acids supported on silica-alumina, obtained by the sol-gel method, catalyze the reaction. The prepared catalysts were characterized by X-ray diffraction and diffuse reflectance spectroscopy. The specific surface area of the catalysts was determined by the nitrogen adsorption/desorption at 196 °C technique, and the catalyst acidity was measured by potentiometric titration with n-butylamine. The heteropolyacid amount removed from the catalysts during the leaching with toluene was lower than 1%. The products were obtained with high conversion and selectivity. The yields were in the 87-96% range for the majority of the selected samples, with the exception of the azlactones synthesized from 2-nitrobenzaldehyde and cyclohexanone, which gave yields in the 70-80% range. The same catalysts were used several times without appreciable loss of their catalytic activity. A rational mechanism for the azlactone formation catalyzed by the supported heteropolyacid is proposed. © 2008 Elsevier B.V. All rights reserved.
publishDate 2009
dc.date.none.fl_str_mv 2009-01
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/11336/54059
Romanelli, Gustavo Pablo; Autino, Juan Carlos; Vázquez, P.; Pizzio, Luis Rene; Blanco, Mirta Noemi; et al.; A suitable synthesis of azlactones (4-benzylidene-2-phenyloxazolin-5-ones and 4-alkylidene-2-phenyloxazolin-5-ones) catalyzed by silica-alumina supported heteropolyacids; Elsevier Science; Applied Catalysis A: General; 352; 1-2; 1-2009; 208-213
0926-860X
CONICET Digital
CONICET
url http://hdl.handle.net/11336/54059
identifier_str_mv Romanelli, Gustavo Pablo; Autino, Juan Carlos; Vázquez, P.; Pizzio, Luis Rene; Blanco, Mirta Noemi; et al.; A suitable synthesis of azlactones (4-benzylidene-2-phenyloxazolin-5-ones and 4-alkylidene-2-phenyloxazolin-5-ones) catalyzed by silica-alumina supported heteropolyacids; Elsevier Science; Applied Catalysis A: General; 352; 1-2; 1-2009; 208-213
0926-860X
CONICET Digital
CONICET
dc.language.none.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv info:eu-repo/semantics/altIdentifier/doi/10.1016/j.apcata.2008.10.003
info:eu-repo/semantics/altIdentifier/url/https://www.sciencedirect.com/science/article/pii/S0926860X08006273
dc.rights.none.fl_str_mv info:eu-repo/semantics/openAccess
https://creativecommons.org/licenses/by-nc-sa/2.5/ar/
eu_rights_str_mv openAccess
rights_invalid_str_mv https://creativecommons.org/licenses/by-nc-sa/2.5/ar/
dc.format.none.fl_str_mv application/pdf
application/pdf
application/pdf
application/pdf
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dc.publisher.none.fl_str_mv Elsevier Science
publisher.none.fl_str_mv Elsevier Science
dc.source.none.fl_str_mv reponame:CONICET Digital (CONICET)
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reponame_str CONICET Digital (CONICET)
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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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