Convenient Michael addition/beta-elimination approach to the synthesis of 4-benzyl- and 4-aryl-selenyl coumarins using diselenides as selenium sources

Autores
Padilha, Gustavo; Birmann, Paloma T.; Domingues, Micaela; Kaufman, Teodoro Saul; Savegnano, Lucielli; Silveira, Claudio
Año de publicación
2017
Idioma
inglés
Tipo de recurso
artículo
Estado
versión publicada
Descripción
A concise and efficient, two-step approach toward 4-organoselenyl coumarin derivatives from the easily available 4-hydroxycoumarins, is reported. The synthesis was based on conventional tosylation followed by a tandem selena-Michael addition/β-elimination reaction of an aryl-/benzyl-selenolate anion on the corresponding 4-tosyloxycoumarins. The selenolate anions were conveniently generated in situ by exposure of the corresponding diselenides to NaBH4. Selected compounds demonstrated to exhibit antioxidant properties in mice cortex and hippocampus.
Fil: Padilha, Gustavo. Universidade Federal de Santa Maria; Brasil
Fil: Birmann, Paloma T.. Universidade Federal de Pelotas; Brasil
Fil: Domingues, Micaela. Universidade Federal de Pelotas; Brasil
Fil: Kaufman, Teodoro Saul. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Rosario. Instituto de Química Rosario. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas. Instituto de Química Rosario; Argentina
Fil: Savegnano, Lucielli. Universidade Federal de Pelotas; Brasil
Fil: Silveira, Claudio. Universidade Federal de Santa Maria; Brasil
Materia
FUNCTIONALIZED COUMARINS
HETEROCYCLIC DERIVATIVES
SELENA-MICHAEL ADDITION/Β-ELIMINATION
SELENOCOUMARINS
SELENOFUNCTIONALIZATION
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:11336/174367
Acceder
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oai_identifier_str oai:ri.conicet.gov.ar:11336/174367
network_acronym_str CONICETDig
repository_id_str 3498
network_name_str CONICET Digital (CONICET)
spelling Convenient Michael addition/beta-elimination approach to the synthesis of 4-benzyl- and 4-aryl-selenyl coumarins using diselenides as selenium sourcesPadilha, GustavoBirmann, Paloma T.Domingues, MicaelaKaufman, Teodoro SaulSavegnano, LucielliSilveira, ClaudioFUNCTIONALIZED COUMARINSHETEROCYCLIC DERIVATIVESSELENA-MICHAEL ADDITION/Β-ELIMINATIONSELENOCOUMARINSSELENOFUNCTIONALIZATIONhttps://purl.org/becyt/ford/1.4https://purl.org/becyt/ford/1A concise and efficient, two-step approach toward 4-organoselenyl coumarin derivatives from the easily available 4-hydroxycoumarins, is reported. The synthesis was based on conventional tosylation followed by a tandem selena-Michael addition/β-elimination reaction of an aryl-/benzyl-selenolate anion on the corresponding 4-tosyloxycoumarins. The selenolate anions were conveniently generated in situ by exposure of the corresponding diselenides to NaBH4. Selected compounds demonstrated to exhibit antioxidant properties in mice cortex and hippocampus.Fil: Padilha, Gustavo. Universidade Federal de Santa Maria; BrasilFil: Birmann, Paloma T.. Universidade Federal de Pelotas; BrasilFil: Domingues, Micaela. Universidade Federal de Pelotas; BrasilFil: Kaufman, Teodoro Saul. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Rosario. Instituto de Química Rosario. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas. Instituto de Química Rosario; ArgentinaFil: Savegnano, Lucielli. Universidade Federal de Pelotas; BrasilFil: Silveira, Claudio. Universidade Federal de Santa Maria; BrasilPergamon-Elsevier Science Ltd2017-03info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionhttp://purl.org/coar/resource_type/c_6501info:ar-repo/semantics/articuloapplication/pdfapplication/pdfhttp://hdl.handle.net/11336/174367Padilha, Gustavo; Birmann, Paloma T.; Domingues, Micaela; Kaufman, Teodoro Saul; Savegnano, Lucielli; et al.; Convenient Michael addition/beta-elimination approach to the synthesis of 4-benzyl- and 4-aryl-selenyl coumarins using diselenides as selenium sources; Pergamon-Elsevier Science Ltd; Tetrahedron Letters; 58; 10; 3-2017; 985-9900040-4039CONICET DigitalCONICETenginfo:eu-repo/semantics/altIdentifier/url/https://www.sciencedirect.com/science/article/pii/S0040403917301284?via%3Dihubinfo:eu-repo/semantics/altIdentifier/doi/10.1016/j.tetlet.2017.01.084info:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by-nc-sa/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2025-09-29T09:34:43Zoai:ri.conicet.gov.ar:11336/174367instacron: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 09:34:43.843CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse
dc.title.none.fl_str_mv Convenient Michael addition/beta-elimination approach to the synthesis of 4-benzyl- and 4-aryl-selenyl coumarins using diselenides as selenium sources
title Convenient Michael addition/beta-elimination approach to the synthesis of 4-benzyl- and 4-aryl-selenyl coumarins using diselenides as selenium sources
spellingShingle Convenient Michael addition/beta-elimination approach to the synthesis of 4-benzyl- and 4-aryl-selenyl coumarins using diselenides as selenium sources
Padilha, Gustavo
FUNCTIONALIZED COUMARINS
HETEROCYCLIC DERIVATIVES
SELENA-MICHAEL ADDITION/Β-ELIMINATION
SELENOCOUMARINS
SELENOFUNCTIONALIZATION
title_short Convenient Michael addition/beta-elimination approach to the synthesis of 4-benzyl- and 4-aryl-selenyl coumarins using diselenides as selenium sources
title_full Convenient Michael addition/beta-elimination approach to the synthesis of 4-benzyl- and 4-aryl-selenyl coumarins using diselenides as selenium sources
title_fullStr Convenient Michael addition/beta-elimination approach to the synthesis of 4-benzyl- and 4-aryl-selenyl coumarins using diselenides as selenium sources
title_full_unstemmed Convenient Michael addition/beta-elimination approach to the synthesis of 4-benzyl- and 4-aryl-selenyl coumarins using diselenides as selenium sources
title_sort Convenient Michael addition/beta-elimination approach to the synthesis of 4-benzyl- and 4-aryl-selenyl coumarins using diselenides as selenium sources
dc.creator.none.fl_str_mv Padilha, Gustavo
Birmann, Paloma T.
Domingues, Micaela
Kaufman, Teodoro Saul
Savegnano, Lucielli
Silveira, Claudio
author Padilha, Gustavo
author_facet Padilha, Gustavo
Birmann, Paloma T.
Domingues, Micaela
Kaufman, Teodoro Saul
Savegnano, Lucielli
Silveira, Claudio
author_role author
author2 Birmann, Paloma T.
Domingues, Micaela
Kaufman, Teodoro Saul
Savegnano, Lucielli
Silveira, Claudio
author2_role author
author
author
author
author
dc.subject.none.fl_str_mv FUNCTIONALIZED COUMARINS
HETEROCYCLIC DERIVATIVES
SELENA-MICHAEL ADDITION/Β-ELIMINATION
SELENOCOUMARINS
SELENOFUNCTIONALIZATION
topic FUNCTIONALIZED COUMARINS
HETEROCYCLIC DERIVATIVES
SELENA-MICHAEL ADDITION/Β-ELIMINATION
SELENOCOUMARINS
SELENOFUNCTIONALIZATION
purl_subject.fl_str_mv https://purl.org/becyt/ford/1.4
https://purl.org/becyt/ford/1
dc.description.none.fl_txt_mv A concise and efficient, two-step approach toward 4-organoselenyl coumarin derivatives from the easily available 4-hydroxycoumarins, is reported. The synthesis was based on conventional tosylation followed by a tandem selena-Michael addition/β-elimination reaction of an aryl-/benzyl-selenolate anion on the corresponding 4-tosyloxycoumarins. The selenolate anions were conveniently generated in situ by exposure of the corresponding diselenides to NaBH4. Selected compounds demonstrated to exhibit antioxidant properties in mice cortex and hippocampus.
Fil: Padilha, Gustavo. Universidade Federal de Santa Maria; Brasil
Fil: Birmann, Paloma T.. Universidade Federal de Pelotas; Brasil
Fil: Domingues, Micaela. Universidade Federal de Pelotas; Brasil
Fil: Kaufman, Teodoro Saul. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Rosario. Instituto de Química Rosario. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas. Instituto de Química Rosario; Argentina
Fil: Savegnano, Lucielli. Universidade Federal de Pelotas; Brasil
Fil: Silveira, Claudio. Universidade Federal de Santa Maria; Brasil
description A concise and efficient, two-step approach toward 4-organoselenyl coumarin derivatives from the easily available 4-hydroxycoumarins, is reported. The synthesis was based on conventional tosylation followed by a tandem selena-Michael addition/β-elimination reaction of an aryl-/benzyl-selenolate anion on the corresponding 4-tosyloxycoumarins. The selenolate anions were conveniently generated in situ by exposure of the corresponding diselenides to NaBH4. Selected compounds demonstrated to exhibit antioxidant properties in mice cortex and hippocampus.
publishDate 2017
dc.date.none.fl_str_mv 2017-03
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/11336/174367
Padilha, Gustavo; Birmann, Paloma T.; Domingues, Micaela; Kaufman, Teodoro Saul; Savegnano, Lucielli; et al.; Convenient Michael addition/beta-elimination approach to the synthesis of 4-benzyl- and 4-aryl-selenyl coumarins using diselenides as selenium sources; Pergamon-Elsevier Science Ltd; Tetrahedron Letters; 58; 10; 3-2017; 985-990
0040-4039
CONICET Digital
CONICET
url http://hdl.handle.net/11336/174367
identifier_str_mv Padilha, Gustavo; Birmann, Paloma T.; Domingues, Micaela; Kaufman, Teodoro Saul; Savegnano, Lucielli; et al.; Convenient Michael addition/beta-elimination approach to the synthesis of 4-benzyl- and 4-aryl-selenyl coumarins using diselenides as selenium sources; Pergamon-Elsevier Science Ltd; Tetrahedron Letters; 58; 10; 3-2017; 985-990
0040-4039
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.sciencedirect.com/science/article/pii/S0040403917301284?via%3Dihub
info:eu-repo/semantics/altIdentifier/doi/10.1016/j.tetlet.2017.01.084
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 Pergamon-Elsevier Science Ltd
publisher.none.fl_str_mv Pergamon-Elsevier Science Ltd
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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