Microwave-assisted multicomponent synthesis of julolidines using silicasupported calix[4]arene as heterogeneous catalyst

Autores
de Paiva, Walysson F.; Braga, Ingredy B.; de Assis, Joao V.; Castañeda, Sandra M. B.; Sathicq, Angel Gabriel; Palermo, Valeria; Romanelli, Gustavo Pablo; Natalino, Ricardo; da Silva, Marcio J.; Martins, Felipe T.; de Carvalho.Gustavo S. G.; Amarante, Giovanni W.; Fernandes, Sergio A.
Año de publicación
2020
Idioma
inglés
Tipo de recurso
documento de conferencia
Estado
versión publicada
Descripción
In this work, the multicomponent Povarov reaction was used for the synthesis of tetrahydrofuranjulolidines catalyzed by Si(n)CX[4]SO3H and assisted by microwave. The heterogeneous catalyst was synthesized from the p-sulfonic acid calix[4]arene by the sol-gel technique. The Povarov reaction is a multicomponent reaction between an aniline, an aldehyde and an alkene or alkyne, catalyzed by Lewis or Brønsted acids, and can provide tetrahydroquinolines, quinolines or julolidines as products, depending on the reactive conditions employed. In this work, 24 julolidines were synthesized from different p-substituted anilines, formaldehyde and 2,3-dihydrofuran. The optimized conditions for the synthesis were: aniline (0.5 mmol), formaldehyde (1.5 mmol), 2,3-dihydrofuran (1.5 mmol), temperature of 150 °C, reaction time of 10 minutes, catalyst concentration of 0.5 mol%, in the absence of solvents. Yields ranged from 58 to 97%. The julolidines were obtained as a mixture of diastereoisomers, which were separated by a silica gel chromatography column, providing 12 julolidines with cis stereochemistry and 12 julolidines with (±)-trans stereochemistry. Compounds were identified and characterized by mass spectrometry, infrared spectroscopy, chiral column HPLC and 1H and 13C Nuclear Magnetic Resonance. The great advantage of the developed methodology is the short reaction time, the operational simplicity and the absence of solvents, factors that help to reduce the formation of residues and go according to the principles of green chemistry.
Fil: de Paiva, Walysson F.. Universidade Federal de Viçosa; Brasil
Fil: Braga, Ingredy B.. Universidade Federal de Viçosa; Brasil
Fil: de Assis, Joao V.. Universidade Federal de Viçosa; Brasil
Fil: Castañeda, Sandra M. B.. Universidade Federal de Viçosa; Brasil
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: Palermo, Valeria. 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: 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: Natalino, Ricardo. Universidade Federal de Viçosa; Brasil
Fil: da Silva, Marcio J.. Universidade Federal de Viçosa; Brasil
Fil: Martins, Felipe T.. Universidade Federal de Goiás; Brasil
Fil: de Carvalho.Gustavo S. G.. Universidade Federal de Juiz de Fora; Brasil
Fil: Amarante, Giovanni W.. Universidade Federal de Juiz de Fora; Brasil
Fil: Fernandes, Sergio A.. Universidade Federal de Viçosa; Brasil
43a Reunião Anual da Sociedade Brasileira de Química: Ciência e ensino para todos
Brasil
Sociedade Brasileira de Química
Materia
Calix[n]arenes
Heterogeneous catalysis
Julolidines
Microwave-assisted
Multicomponent reactions
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:11336/262120
Acceder
id CONICETDig_3cf8fbf48565770dab55d53e2c1fd8b2
oai_identifier_str oai:ri.conicet.gov.ar:11336/262120
network_acronym_str CONICETDig
repository_id_str 3498
network_name_str CONICET Digital (CONICET)
spelling Microwave-assisted multicomponent synthesis of julolidines using silicasupported calix[4]arene as heterogeneous catalystde Paiva, Walysson F.Braga, Ingredy B.de Assis, Joao V.Castañeda, Sandra M. B.Sathicq, Angel GabrielPalermo, ValeriaRomanelli, Gustavo PabloNatalino, Ricardoda Silva, Marcio J.Martins, Felipe T.de Carvalho.Gustavo S. G.Amarante, Giovanni W.Fernandes, Sergio A.Calix[n]arenesHeterogeneous catalysisJulolidinesMicrowave-assistedMulticomponent reactionshttps://purl.org/becyt/ford/1.4https://purl.org/becyt/ford/1In this work, the multicomponent Povarov reaction was used for the synthesis of tetrahydrofuranjulolidines catalyzed by Si(n)CX[4]SO3H and assisted by microwave. The heterogeneous catalyst was synthesized from the p-sulfonic acid calix[4]arene by the sol-gel technique. The Povarov reaction is a multicomponent reaction between an aniline, an aldehyde and an alkene or alkyne, catalyzed by Lewis or Brønsted acids, and can provide tetrahydroquinolines, quinolines or julolidines as products, depending on the reactive conditions employed. In this work, 24 julolidines were synthesized from different p-substituted anilines, formaldehyde and 2,3-dihydrofuran. The optimized conditions for the synthesis were: aniline (0.5 mmol), formaldehyde (1.5 mmol), 2,3-dihydrofuran (1.5 mmol), temperature of 150 °C, reaction time of 10 minutes, catalyst concentration of 0.5 mol%, in the absence of solvents. Yields ranged from 58 to 97%. The julolidines were obtained as a mixture of diastereoisomers, which were separated by a silica gel chromatography column, providing 12 julolidines with cis stereochemistry and 12 julolidines with (±)-trans stereochemistry. Compounds were identified and characterized by mass spectrometry, infrared spectroscopy, chiral column HPLC and 1H and 13C Nuclear Magnetic Resonance. The great advantage of the developed methodology is the short reaction time, the operational simplicity and the absence of solvents, factors that help to reduce the formation of residues and go according to the principles of green chemistry.Fil: de Paiva, Walysson F.. Universidade Federal de Viçosa; BrasilFil: Braga, Ingredy B.. Universidade Federal de Viçosa; BrasilFil: de Assis, Joao V.. Universidade Federal de Viçosa; BrasilFil: Castañeda, Sandra M. B.. Universidade Federal de Viçosa; BrasilFil: 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: Palermo, Valeria. 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: 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: Natalino, Ricardo. Universidade Federal de Viçosa; BrasilFil: da Silva, Marcio J.. Universidade Federal de Viçosa; BrasilFil: Martins, Felipe T.. Universidade Federal de Goiás; BrasilFil: de Carvalho.Gustavo S. G.. Universidade Federal de Juiz de Fora; BrasilFil: Amarante, Giovanni W.. Universidade Federal de Juiz de Fora; BrasilFil: Fernandes, Sergio A.. Universidade Federal de Viçosa; Brasil43a Reunião Anual da Sociedade Brasileira de Química: Ciência e ensino para todosBrasilSociedade Brasileira de QuímicaSociedade Brasileira de Química2020info:eu-repo/semantics/publishedVersioninfo:eu-repo/semantics/conferenceObjectVirtualBookhttp://purl.org/coar/resource_type/c_5794info:ar-repo/semantics/documentoDeConferenciaapplication/pdfapplication/pdfhttp://hdl.handle.net/11336/262120Microwave-assisted multicomponent synthesis of julolidines using silicasupported calix[4]arene as heterogeneous catalyst; 43a Reunião Anual da Sociedade Brasileira de Química: Ciência e ensino para todos; Brasil; 2020; 1-1CONICET DigitalCONICETenginfo:eu-repo/semantics/altIdentifier/url/https://www.sbq.org.br/43ra/anexos/43RASBQ_resumos.pdfinfo:eu-repo/semantics/altIdentifier/url/https://proceedings.science/rasbq-2020/trabalhos/microwave-assisted-multicomponent-synthesis-of-julolidines-using-silica-supporte?lang=pt-brNacionalinfo:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by-nc-sa/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2025-10-15T14:47:49Zoai:ri.conicet.gov.ar:11336/262120instacron: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:34982025-10-15 14:47:49.295CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse
dc.title.none.fl_str_mv Microwave-assisted multicomponent synthesis of julolidines using silicasupported calix[4]arene as heterogeneous catalyst
title Microwave-assisted multicomponent synthesis of julolidines using silicasupported calix[4]arene as heterogeneous catalyst
spellingShingle Microwave-assisted multicomponent synthesis of julolidines using silicasupported calix[4]arene as heterogeneous catalyst
de Paiva, Walysson F.
Calix[n]arenes
Heterogeneous catalysis
Julolidines
Microwave-assisted
Multicomponent reactions
title_short Microwave-assisted multicomponent synthesis of julolidines using silicasupported calix[4]arene as heterogeneous catalyst
title_full Microwave-assisted multicomponent synthesis of julolidines using silicasupported calix[4]arene as heterogeneous catalyst
title_fullStr Microwave-assisted multicomponent synthesis of julolidines using silicasupported calix[4]arene as heterogeneous catalyst
title_full_unstemmed Microwave-assisted multicomponent synthesis of julolidines using silicasupported calix[4]arene as heterogeneous catalyst
title_sort Microwave-assisted multicomponent synthesis of julolidines using silicasupported calix[4]arene as heterogeneous catalyst
dc.creator.none.fl_str_mv de Paiva, Walysson F.
Braga, Ingredy B.
de Assis, Joao V.
Castañeda, Sandra M. B.
Sathicq, Angel Gabriel
Palermo, Valeria
Romanelli, Gustavo Pablo
Natalino, Ricardo
da Silva, Marcio J.
Martins, Felipe T.
de Carvalho.Gustavo S. G.
Amarante, Giovanni W.
Fernandes, Sergio A.
author de Paiva, Walysson F.
author_facet de Paiva, Walysson F.
Braga, Ingredy B.
de Assis, Joao V.
Castañeda, Sandra M. B.
Sathicq, Angel Gabriel
Palermo, Valeria
Romanelli, Gustavo Pablo
Natalino, Ricardo
da Silva, Marcio J.
Martins, Felipe T.
de Carvalho.Gustavo S. G.
Amarante, Giovanni W.
Fernandes, Sergio A.
author_role author
author2 Braga, Ingredy B.
de Assis, Joao V.
Castañeda, Sandra M. B.
Sathicq, Angel Gabriel
Palermo, Valeria
Romanelli, Gustavo Pablo
Natalino, Ricardo
da Silva, Marcio J.
Martins, Felipe T.
de Carvalho.Gustavo S. G.
Amarante, Giovanni W.
Fernandes, Sergio A.
author2_role author
author
author
author
author
author
author
author
author
author
author
author
dc.subject.none.fl_str_mv Calix[n]arenes
Heterogeneous catalysis
Julolidines
Microwave-assisted
Multicomponent reactions
topic Calix[n]arenes
Heterogeneous catalysis
Julolidines
Microwave-assisted
Multicomponent reactions
purl_subject.fl_str_mv https://purl.org/becyt/ford/1.4
https://purl.org/becyt/ford/1
dc.description.none.fl_txt_mv In this work, the multicomponent Povarov reaction was used for the synthesis of tetrahydrofuranjulolidines catalyzed by Si(n)CX[4]SO3H and assisted by microwave. The heterogeneous catalyst was synthesized from the p-sulfonic acid calix[4]arene by the sol-gel technique. The Povarov reaction is a multicomponent reaction between an aniline, an aldehyde and an alkene or alkyne, catalyzed by Lewis or Brønsted acids, and can provide tetrahydroquinolines, quinolines or julolidines as products, depending on the reactive conditions employed. In this work, 24 julolidines were synthesized from different p-substituted anilines, formaldehyde and 2,3-dihydrofuran. The optimized conditions for the synthesis were: aniline (0.5 mmol), formaldehyde (1.5 mmol), 2,3-dihydrofuran (1.5 mmol), temperature of 150 °C, reaction time of 10 minutes, catalyst concentration of 0.5 mol%, in the absence of solvents. Yields ranged from 58 to 97%. The julolidines were obtained as a mixture of diastereoisomers, which were separated by a silica gel chromatography column, providing 12 julolidines with cis stereochemistry and 12 julolidines with (±)-trans stereochemistry. Compounds were identified and characterized by mass spectrometry, infrared spectroscopy, chiral column HPLC and 1H and 13C Nuclear Magnetic Resonance. The great advantage of the developed methodology is the short reaction time, the operational simplicity and the absence of solvents, factors that help to reduce the formation of residues and go according to the principles of green chemistry.
Fil: de Paiva, Walysson F.. Universidade Federal de Viçosa; Brasil
Fil: Braga, Ingredy B.. Universidade Federal de Viçosa; Brasil
Fil: de Assis, Joao V.. Universidade Federal de Viçosa; Brasil
Fil: Castañeda, Sandra M. B.. Universidade Federal de Viçosa; Brasil
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: Palermo, Valeria. 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: 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: Natalino, Ricardo. Universidade Federal de Viçosa; Brasil
Fil: da Silva, Marcio J.. Universidade Federal de Viçosa; Brasil
Fil: Martins, Felipe T.. Universidade Federal de Goiás; Brasil
Fil: de Carvalho.Gustavo S. G.. Universidade Federal de Juiz de Fora; Brasil
Fil: Amarante, Giovanni W.. Universidade Federal de Juiz de Fora; Brasil
Fil: Fernandes, Sergio A.. Universidade Federal de Viçosa; Brasil
43a Reunião Anual da Sociedade Brasileira de Química: Ciência e ensino para todos
Brasil
Sociedade Brasileira de Química
description In this work, the multicomponent Povarov reaction was used for the synthesis of tetrahydrofuranjulolidines catalyzed by Si(n)CX[4]SO3H and assisted by microwave. The heterogeneous catalyst was synthesized from the p-sulfonic acid calix[4]arene by the sol-gel technique. The Povarov reaction is a multicomponent reaction between an aniline, an aldehyde and an alkene or alkyne, catalyzed by Lewis or Brønsted acids, and can provide tetrahydroquinolines, quinolines or julolidines as products, depending on the reactive conditions employed. In this work, 24 julolidines were synthesized from different p-substituted anilines, formaldehyde and 2,3-dihydrofuran. The optimized conditions for the synthesis were: aniline (0.5 mmol), formaldehyde (1.5 mmol), 2,3-dihydrofuran (1.5 mmol), temperature of 150 °C, reaction time of 10 minutes, catalyst concentration of 0.5 mol%, in the absence of solvents. Yields ranged from 58 to 97%. The julolidines were obtained as a mixture of diastereoisomers, which were separated by a silica gel chromatography column, providing 12 julolidines with cis stereochemistry and 12 julolidines with (±)-trans stereochemistry. Compounds were identified and characterized by mass spectrometry, infrared spectroscopy, chiral column HPLC and 1H and 13C Nuclear Magnetic Resonance. The great advantage of the developed methodology is the short reaction time, the operational simplicity and the absence of solvents, factors that help to reduce the formation of residues and go according to the principles of green chemistry.
publishDate 2020
dc.date.none.fl_str_mv 2020
dc.type.none.fl_str_mv info:eu-repo/semantics/publishedVersion
info:eu-repo/semantics/conferenceObject
Virtual
Book
http://purl.org/coar/resource_type/c_5794
info:ar-repo/semantics/documentoDeConferencia
status_str publishedVersion
format conferenceObject
dc.identifier.none.fl_str_mv http://hdl.handle.net/11336/262120
Microwave-assisted multicomponent synthesis of julolidines using silicasupported calix[4]arene as heterogeneous catalyst; 43a Reunião Anual da Sociedade Brasileira de Química: Ciência e ensino para todos; Brasil; 2020; 1-1
CONICET Digital
CONICET
url http://hdl.handle.net/11336/262120
identifier_str_mv Microwave-assisted multicomponent synthesis of julolidines using silicasupported calix[4]arene as heterogeneous catalyst; 43a Reunião Anual da Sociedade Brasileira de Química: Ciência e ensino para todos; Brasil; 2020; 1-1
CONICET Digital
CONICET
dc.language.none.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv info:eu-repo/semantics/altIdentifier/url/https://www.sbq.org.br/43ra/anexos/43RASBQ_resumos.pdf
info:eu-repo/semantics/altIdentifier/url/https://proceedings.science/rasbq-2020/trabalhos/microwave-assisted-multicomponent-synthesis-of-julolidines-using-silica-supporte?lang=pt-br
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/
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application/pdf
dc.coverage.none.fl_str_mv Nacional
dc.publisher.none.fl_str_mv Sociedade Brasileira de Química
publisher.none.fl_str_mv Sociedade Brasileira de Química
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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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