Single-step synthesis of 4-phenyl and 3,4-dihydro-4-phenyl coumarins using a recyclable Preyssler heteropolyacid catalyst under solvent-free reaction conditions

Autores
Escobar Caicedo, Angélica María; Ruiz, Diego Manuel; Romanelli, Gustavo Pablo; Autino, Juan Carlos
Año de publicación
2015
Idioma
inglés
Tipo de recurso
artículo
Estado
versión publicada
Descripción
4-Phenyl and 3,4-dihydro-4-phenylcoumarins were prepared by direct esterification of phenols with phenylpropiolic and cinnamic acids, respectively, using a compound with Preyssler structure (H14P5NaW30O110) (PA) as heterogeneous catalyst under solvent-free reaction conditions, at 130 C, in a short reaction time (2 h). Underthese conditions, very good yields (11 examples: 61 %–90 %), free of secondary products, were obtained. The catalyst is recyclable, nontoxic, neither air nor moisture sensitive, and easy to handle. The described methodology is a clean and useful alternative to synthesize oxygenated heterocycles based on a coumarin skeleton.
Fil: Escobar Caicedo, Angélica María. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico la Plata. Centro de Investigación y Desarrollo En Ciencias Aplicadas; Argentina
Fil: Ruiz, Diego Manuel. Universidad Nacional de la Plata. Facultad de Ciencias Agrarias y Forestales. Departamento de Ciencias Exactas. Catedra de Quimica Organica; Argentina
Fil: Romanelli, Gustavo Pablo. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico la Plata. 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. Catedra de Quimica Organica; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico La Plata. Centro de Investigación y Desarrollo en Ciencias Aplicadas; Argentina
Materia
4-Phenylcoumarins
4-Phenyl-3 4-Dihydrocoumarins
Preyssler Catalyst
Solvent-Free Reaction Conditions
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:11336/6370
Acceder
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network_acronym_str CONICETDig
repository_id_str 3498
network_name_str CONICET Digital (CONICET)
spelling Single-step synthesis of 4-phenyl and 3,4-dihydro-4-phenyl coumarins using a recyclable Preyssler heteropolyacid catalyst under solvent-free reaction conditionsEscobar Caicedo, Angélica MaríaRuiz, Diego ManuelRomanelli, Gustavo PabloAutino, Juan Carlos4-Phenylcoumarins4-Phenyl-3 4-DihydrocoumarinsPreyssler CatalystSolvent-Free Reaction Conditionshttps://purl.org/becyt/ford/2.4https://purl.org/becyt/ford/2https://purl.org/becyt/ford/1.4https://purl.org/becyt/ford/14-Phenyl and 3,4-dihydro-4-phenylcoumarins were prepared by direct esterification of phenols with phenylpropiolic and cinnamic acids, respectively, using a compound with Preyssler structure (H14P5NaW30O110) (PA) as heterogeneous catalyst under solvent-free reaction conditions, at 130 C, in a short reaction time (2 h). Underthese conditions, very good yields (11 examples: 61 %–90 %), free of secondary products, were obtained. The catalyst is recyclable, nontoxic, neither air nor moisture sensitive, and easy to handle. The described methodology is a clean and useful alternative to synthesize oxygenated heterocycles based on a coumarin skeleton.Fil: Escobar Caicedo, Angélica María. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico la Plata. Centro de Investigación y Desarrollo En Ciencias Aplicadas; ArgentinaFil: Ruiz, Diego Manuel. Universidad Nacional de la Plata. Facultad de Ciencias Agrarias y Forestales. Departamento de Ciencias Exactas. Catedra de Quimica Organica; ArgentinaFil: Romanelli, Gustavo Pablo. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico la Plata. 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. Catedra de Quimica Organica; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico La Plata. Centro de Investigación y Desarrollo en Ciencias Aplicadas; ArgentinaSpringer2015-04-17info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionhttp://purl.org/coar/resource_type/c_6501info:ar-repo/semantics/articuloapplication/pdfapplication/pdfhttp://hdl.handle.net/11336/6370Escobar Caicedo, Angélica María; Ruiz, Diego Manuel; Romanelli, Gustavo Pablo; Autino, Juan Carlos; Single-step synthesis of 4-phenyl and 3,4-dihydro-4-phenyl coumarins using a recyclable Preyssler heteropolyacid catalyst under solvent-free reaction conditions; Springer; Research on Chemical Intermediates; 41; 12; 17-4-2015; 10109-101230922-61681568-5675enginfo:eu-repo/semantics/altIdentifier/doi/10.1007/s11164-015-2016-3info:eu-repo/semantics/altIdentifier/doi/info:eu-repo/semantics/altIdentifier/url/http://link.springer.com/article/10.1007%2Fs11164-015-2016-3info:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by-nc-sa/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2025-09-29T09:42:07Zoai:ri.conicet.gov.ar:11336/6370instacron: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 09:42:07.39CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse
dc.title.none.fl_str_mv Single-step synthesis of 4-phenyl and 3,4-dihydro-4-phenyl coumarins using a recyclable Preyssler heteropolyacid catalyst under solvent-free reaction conditions
title Single-step synthesis of 4-phenyl and 3,4-dihydro-4-phenyl coumarins using a recyclable Preyssler heteropolyacid catalyst under solvent-free reaction conditions
spellingShingle Single-step synthesis of 4-phenyl and 3,4-dihydro-4-phenyl coumarins using a recyclable Preyssler heteropolyacid catalyst under solvent-free reaction conditions
Escobar Caicedo, Angélica María
4-Phenylcoumarins
4-Phenyl-3 4-Dihydrocoumarins
Preyssler Catalyst
Solvent-Free Reaction Conditions
title_short Single-step synthesis of 4-phenyl and 3,4-dihydro-4-phenyl coumarins using a recyclable Preyssler heteropolyacid catalyst under solvent-free reaction conditions
title_full Single-step synthesis of 4-phenyl and 3,4-dihydro-4-phenyl coumarins using a recyclable Preyssler heteropolyacid catalyst under solvent-free reaction conditions
title_fullStr Single-step synthesis of 4-phenyl and 3,4-dihydro-4-phenyl coumarins using a recyclable Preyssler heteropolyacid catalyst under solvent-free reaction conditions
title_full_unstemmed Single-step synthesis of 4-phenyl and 3,4-dihydro-4-phenyl coumarins using a recyclable Preyssler heteropolyacid catalyst under solvent-free reaction conditions
title_sort Single-step synthesis of 4-phenyl and 3,4-dihydro-4-phenyl coumarins using a recyclable Preyssler heteropolyacid catalyst under solvent-free reaction conditions
dc.creator.none.fl_str_mv Escobar Caicedo, Angélica María
Ruiz, Diego Manuel
Romanelli, Gustavo Pablo
Autino, Juan Carlos
author Escobar Caicedo, Angélica María
author_facet Escobar Caicedo, Angélica María
Ruiz, Diego Manuel
Romanelli, Gustavo Pablo
Autino, Juan Carlos
author_role author
author2 Ruiz, Diego Manuel
Romanelli, Gustavo Pablo
Autino, Juan Carlos
author2_role author
author
author
dc.subject.none.fl_str_mv 4-Phenylcoumarins
4-Phenyl-3 4-Dihydrocoumarins
Preyssler Catalyst
Solvent-Free Reaction Conditions
topic 4-Phenylcoumarins
4-Phenyl-3 4-Dihydrocoumarins
Preyssler Catalyst
Solvent-Free Reaction Conditions
purl_subject.fl_str_mv https://purl.org/becyt/ford/2.4
https://purl.org/becyt/ford/2
https://purl.org/becyt/ford/1.4
https://purl.org/becyt/ford/1
dc.description.none.fl_txt_mv 4-Phenyl and 3,4-dihydro-4-phenylcoumarins were prepared by direct esterification of phenols with phenylpropiolic and cinnamic acids, respectively, using a compound with Preyssler structure (H14P5NaW30O110) (PA) as heterogeneous catalyst under solvent-free reaction conditions, at 130 C, in a short reaction time (2 h). Underthese conditions, very good yields (11 examples: 61 %–90 %), free of secondary products, were obtained. The catalyst is recyclable, nontoxic, neither air nor moisture sensitive, and easy to handle. The described methodology is a clean and useful alternative to synthesize oxygenated heterocycles based on a coumarin skeleton.
Fil: Escobar Caicedo, Angélica María. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico la Plata. Centro de Investigación y Desarrollo En Ciencias Aplicadas; Argentina
Fil: Ruiz, Diego Manuel. Universidad Nacional de la Plata. Facultad de Ciencias Agrarias y Forestales. Departamento de Ciencias Exactas. Catedra de Quimica Organica; Argentina
Fil: Romanelli, Gustavo Pablo. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico la Plata. 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. Catedra de Quimica Organica; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico La Plata. Centro de Investigación y Desarrollo en Ciencias Aplicadas; Argentina
description 4-Phenyl and 3,4-dihydro-4-phenylcoumarins were prepared by direct esterification of phenols with phenylpropiolic and cinnamic acids, respectively, using a compound with Preyssler structure (H14P5NaW30O110) (PA) as heterogeneous catalyst under solvent-free reaction conditions, at 130 C, in a short reaction time (2 h). Underthese conditions, very good yields (11 examples: 61 %–90 %), free of secondary products, were obtained. The catalyst is recyclable, nontoxic, neither air nor moisture sensitive, and easy to handle. The described methodology is a clean and useful alternative to synthesize oxygenated heterocycles based on a coumarin skeleton.
publishDate 2015
dc.date.none.fl_str_mv 2015-04-17
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/11336/6370
Escobar Caicedo, Angélica María; Ruiz, Diego Manuel; Romanelli, Gustavo Pablo; Autino, Juan Carlos; Single-step synthesis of 4-phenyl and 3,4-dihydro-4-phenyl coumarins using a recyclable Preyssler heteropolyacid catalyst under solvent-free reaction conditions; Springer; Research on Chemical Intermediates; 41; 12; 17-4-2015; 10109-10123
0922-6168
1568-5675
url http://hdl.handle.net/11336/6370
identifier_str_mv Escobar Caicedo, Angélica María; Ruiz, Diego Manuel; Romanelli, Gustavo Pablo; Autino, Juan Carlos; Single-step synthesis of 4-phenyl and 3,4-dihydro-4-phenyl coumarins using a recyclable Preyssler heteropolyacid catalyst under solvent-free reaction conditions; Springer; Research on Chemical Intermediates; 41; 12; 17-4-2015; 10109-10123
0922-6168
1568-5675
dc.language.none.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv info:eu-repo/semantics/altIdentifier/doi/10.1007/s11164-015-2016-3
info:eu-repo/semantics/altIdentifier/doi/
info:eu-repo/semantics/altIdentifier/url/http://link.springer.com/article/10.1007%2Fs11164-015-2016-3
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
dc.publisher.none.fl_str_mv Springer
publisher.none.fl_str_mv Springer
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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