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
- Institución
- Consejo Nacional de Investigaciones Científicas y Técnicas
- OAI Identificador
- oai:ri.conicet.gov.ar:11336/262120
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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 Técnicas2025-09-29T09:52:51Zoai: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:34982025-09-29 09:52:51.459CONICET 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/ |
dc.format.none.fl_str_mv |
application/pdf 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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reponame:CONICET Digital (CONICET) instname:Consejo Nacional de Investigaciones Científicas y Técnicas |
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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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13.070432 |