Microwave-assisted multicomponent synthesis of julolidines using silica- supported 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; 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]SO 3 H 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, analdehyde 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 1 H and 13 C 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 formationof residues and go according to the principles of green chemistry.
Fil: de Paiva, Walysson F.. Universidade Federal de Vicosa; Brasil
Fil: Braga, Ingredy B. Universidade Federal de Vicosa; Brasil
Fil: de Assis, Joao V.. Universidade Federal de Vicosa; Brasil
Fil: Castañeda, Sandra M. B.. Universidade Federal de Vicosa; 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 Vicosa; 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 Vicosa; Brasil
43ª Reunião Anual Virtual da SBQ
No consigna
Brasil
Sociedade Brasileira de Química - Materia
-
Julolidinas
Multicomponent reactions
Heterogeneous catalysis
Calix[n]arenes
Microwave-assisted - 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:11336/233456
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Microwave-assisted multicomponent synthesis of julolidines using silica- supported calix[4]arene as heterogeneous catalystde Paiva, Walysson F.Braga, Ingredy Bde Assis, Joao V.Castañeda, Sandra M. B.Sathicq, Angel GabrielPalermo, ValeriaRomanelli, Gustavo PabloNatalino, RicardoMartins, Felipe T.de Carvalho, Gustavo S.G.Amarante, Giovanni W.Fernandes, Sergio A.JulolidinasMulticomponent reactionsHeterogeneous catalysisCalix[n]arenesMicrowave-assistedhttps://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]SO 3 H 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, analdehyde 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 1 H and 13 C 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 formationof residues and go according to the principles of green chemistry.Fil: de Paiva, Walysson F.. Universidade Federal de Vicosa; BrasilFil: Braga, Ingredy B. Universidade Federal de Vicosa; BrasilFil: de Assis, Joao V.. Universidade Federal de Vicosa; BrasilFil: Castañeda, Sandra M. B.. Universidade Federal de Vicosa; 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 Vicosa; 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 Vicosa; Brasil43ª Reunião Anual Virtual da SBQNo consignaBrasilSociedade Brasileira de QuímicaGaloá2020info:eu-repo/semantics/publishedVersioninfo:eu-repo/semantics/conferenceObjectVirtualBookhttp://purl.org/coar/resource_type/c_5794info:ar-repo/semantics/documentoDeConferenciaapplication/pdfapplication/pdfhttp://hdl.handle.net/11336/233456Microwave-assisted multicomponent synthesis of julolidines using silica- supported calix[4]arene as heterogeneous catalyst; 43ª Reunião Anual Virtual da SBQ; No consigna; Brasil; 2020; 1-1CONICET DigitalCONICETenginfo:eu-repo/semantics/altIdentifier/url/https://www.sbq.org.br/43ra/anexos/43RASBQ_resumos.pdfNacionalinfo:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by-nc-sa/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2025-09-29T09:59:37Zoai:ri.conicet.gov.ar:11336/233456instacron: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 09:59:38.158CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse |
dc.title.none.fl_str_mv |
Microwave-assisted multicomponent synthesis of julolidines using silica- supported calix[4]arene as heterogeneous catalyst |
title |
Microwave-assisted multicomponent synthesis of julolidines using silica- supported calix[4]arene as heterogeneous catalyst |
spellingShingle |
Microwave-assisted multicomponent synthesis of julolidines using silica- supported calix[4]arene as heterogeneous catalyst de Paiva, Walysson F. Julolidinas Multicomponent reactions Heterogeneous catalysis Calix[n]arenes Microwave-assisted |
title_short |
Microwave-assisted multicomponent synthesis of julolidines using silica- supported calix[4]arene as heterogeneous catalyst |
title_full |
Microwave-assisted multicomponent synthesis of julolidines using silica- supported calix[4]arene as heterogeneous catalyst |
title_fullStr |
Microwave-assisted multicomponent synthesis of julolidines using silica- supported calix[4]arene as heterogeneous catalyst |
title_full_unstemmed |
Microwave-assisted multicomponent synthesis of julolidines using silica- supported calix[4]arene as heterogeneous catalyst |
title_sort |
Microwave-assisted multicomponent synthesis of julolidines using silica- supported 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 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 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 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 |
dc.subject.none.fl_str_mv |
Julolidinas Multicomponent reactions Heterogeneous catalysis Calix[n]arenes Microwave-assisted |
topic |
Julolidinas Multicomponent reactions Heterogeneous catalysis Calix[n]arenes Microwave-assisted |
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]SO 3 H 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, analdehyde 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 1 H and 13 C 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 formationof residues and go according to the principles of green chemistry. Fil: de Paiva, Walysson F.. Universidade Federal de Vicosa; Brasil Fil: Braga, Ingredy B. Universidade Federal de Vicosa; Brasil Fil: de Assis, Joao V.. Universidade Federal de Vicosa; Brasil Fil: Castañeda, Sandra M. B.. Universidade Federal de Vicosa; 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 Vicosa; 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 Vicosa; Brasil 43ª Reunião Anual Virtual da SBQ No consigna 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]SO 3 H 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, analdehyde 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 1 H and 13 C 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 formationof 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/11336/233456 Microwave-assisted multicomponent synthesis of julolidines using silica- supported calix[4]arene as heterogeneous catalyst; 43ª Reunião Anual Virtual da SBQ; No consigna; Brasil; 2020; 1-1 CONICET Digital CONICET |
url |
http://hdl.handle.net/11336/233456 |
identifier_str_mv |
Microwave-assisted multicomponent synthesis of julolidines using silica- supported calix[4]arene as heterogeneous catalyst; 43ª Reunião Anual Virtual da SBQ; No consigna; 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 |
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 |
Galoá |
publisher.none.fl_str_mv |
Galoá |
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 |