Efficient synthesis of 4-sulfanylcoumarins from 3-bromo-coumarins: Via a highly selective DABCO-mediated one-pot thia-Michael addition/elimination process

Autores
Mostardeiro, Vitor B.; Dilelio, Marina C.; Kaufman, Teodoro Saul; Silveira, Claudio
Año de publicación
2020
Idioma
inglés
Tipo de recurso
artículo
Estado
versión publicada
Descripción
A facile and efficient protocol for the highly selective direct sulfanylation of 3-bromocoumarins under DABCO promotion, was developed. The transformation took place with aromatic and aliphatic thiols as well as with α,ω-dithiols, affording the expected products in very good to excellent yields. Simple and convenient ways to access 4-((ω-mercaptoalkyl) thio)coumarins and the dimeric 4,4′-(alkane-1,4-diylbis(sulfanediyl))bis(coumarins) were also devised with the use of α,ω-alkanedithiols in different ratios with regards to the starting 3-bromocoumarin. The transformation seems to proceed through the DABCO-mediated thia-Michael stereoselective addition of the thiolate anion to the α,β-unsaturated carbonyl system of the coumarin, followed by a DABCO-assisted stereoselective dehydrobromination of the resulting α-bromo carbonyl intermediate.
Fil: Mostardeiro, Vitor B.. Universidade Federal de Santa Maria; Brasil
Fil: Dilelio, Marina C.. Universidade Federal de Santa Maria; 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: Silveira, Claudio. Universidade Federal de Santa Maria; Brasil
Materia
4-thiocoumarins
3-bromocoumarins
DABCO
Selective reaction
Nivel de accesibilidad
acceso abierto
Condiciones de uso
https://creativecommons.org/licenses/by-nc/2.5/ar/
Repositorio
CONICET Digital (CONICET)
Institución
Consejo Nacional de Investigaciones Científicas y Técnicas
OAI Identificador
oai:ri.conicet.gov.ar:11336/128127
Acceder
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network_name_str CONICET Digital (CONICET)
spelling Efficient synthesis of 4-sulfanylcoumarins from 3-bromo-coumarins: Via a highly selective DABCO-mediated one-pot thia-Michael addition/elimination processMostardeiro, Vitor B.Dilelio, Marina C.Kaufman, Teodoro SaulSilveira, Claudio4-thiocoumarins3-bromocoumarinsDABCOSelective reactionhttps://purl.org/becyt/ford/1.4https://purl.org/becyt/ford/1A facile and efficient protocol for the highly selective direct sulfanylation of 3-bromocoumarins under DABCO promotion, was developed. The transformation took place with aromatic and aliphatic thiols as well as with α,ω-dithiols, affording the expected products in very good to excellent yields. Simple and convenient ways to access 4-((ω-mercaptoalkyl) thio)coumarins and the dimeric 4,4′-(alkane-1,4-diylbis(sulfanediyl))bis(coumarins) were also devised with the use of α,ω-alkanedithiols in different ratios with regards to the starting 3-bromocoumarin. The transformation seems to proceed through the DABCO-mediated thia-Michael stereoselective addition of the thiolate anion to the α,β-unsaturated carbonyl system of the coumarin, followed by a DABCO-assisted stereoselective dehydrobromination of the resulting α-bromo carbonyl intermediate.Fil: Mostardeiro, Vitor B.. Universidade Federal de Santa Maria; BrasilFil: Dilelio, Marina C.. Universidade Federal de Santa Maria; 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: Silveira, Claudio. Universidade Federal de Santa Maria; BrasilRoyal Society of Chemistry2020-01info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionhttp://purl.org/coar/resource_type/c_6501info:ar-repo/semantics/articuloapplication/pdfapplication/pdfhttp://hdl.handle.net/11336/128127Mostardeiro, Vitor B.; Dilelio, Marina C.; Kaufman, Teodoro Saul; Silveira, Claudio; Efficient synthesis of 4-sulfanylcoumarins from 3-bromo-coumarins: Via a highly selective DABCO-mediated one-pot thia-Michael addition/elimination process; Royal Society of Chemistry; RSC Advances; 10; 1; 1-2020; 482-4912046-2069CONICET DigitalCONICETenginfo:eu-repo/semantics/altIdentifier/url/https://pubs.rsc.org/en/content/articlelanding/2020/ra/c9ra09545d#!divAbstractinfo:eu-repo/semantics/altIdentifier/doi/10.1039/C9RA09545Dinfo:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by-nc/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2025-10-22T11:16:57Zoai:ri.conicet.gov.ar:11336/128127instacron: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:34982025-10-22 11:16:58.162CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse
dc.title.none.fl_str_mv Efficient synthesis of 4-sulfanylcoumarins from 3-bromo-coumarins: Via a highly selective DABCO-mediated one-pot thia-Michael addition/elimination process
title Efficient synthesis of 4-sulfanylcoumarins from 3-bromo-coumarins: Via a highly selective DABCO-mediated one-pot thia-Michael addition/elimination process
spellingShingle Efficient synthesis of 4-sulfanylcoumarins from 3-bromo-coumarins: Via a highly selective DABCO-mediated one-pot thia-Michael addition/elimination process
Mostardeiro, Vitor B.
4-thiocoumarins
3-bromocoumarins
DABCO
Selective reaction
title_short Efficient synthesis of 4-sulfanylcoumarins from 3-bromo-coumarins: Via a highly selective DABCO-mediated one-pot thia-Michael addition/elimination process
title_full Efficient synthesis of 4-sulfanylcoumarins from 3-bromo-coumarins: Via a highly selective DABCO-mediated one-pot thia-Michael addition/elimination process
title_fullStr Efficient synthesis of 4-sulfanylcoumarins from 3-bromo-coumarins: Via a highly selective DABCO-mediated one-pot thia-Michael addition/elimination process
title_full_unstemmed Efficient synthesis of 4-sulfanylcoumarins from 3-bromo-coumarins: Via a highly selective DABCO-mediated one-pot thia-Michael addition/elimination process
title_sort Efficient synthesis of 4-sulfanylcoumarins from 3-bromo-coumarins: Via a highly selective DABCO-mediated one-pot thia-Michael addition/elimination process
dc.creator.none.fl_str_mv Mostardeiro, Vitor B.
Dilelio, Marina C.
Kaufman, Teodoro Saul
Silveira, Claudio
author Mostardeiro, Vitor B.
author_facet Mostardeiro, Vitor B.
Dilelio, Marina C.
Kaufman, Teodoro Saul
Silveira, Claudio
author_role author
author2 Dilelio, Marina C.
Kaufman, Teodoro Saul
Silveira, Claudio
author2_role author
author
author
dc.subject.none.fl_str_mv 4-thiocoumarins
3-bromocoumarins
DABCO
Selective reaction
topic 4-thiocoumarins
3-bromocoumarins
DABCO
Selective reaction
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 facile and efficient protocol for the highly selective direct sulfanylation of 3-bromocoumarins under DABCO promotion, was developed. The transformation took place with aromatic and aliphatic thiols as well as with α,ω-dithiols, affording the expected products in very good to excellent yields. Simple and convenient ways to access 4-((ω-mercaptoalkyl) thio)coumarins and the dimeric 4,4′-(alkane-1,4-diylbis(sulfanediyl))bis(coumarins) were also devised with the use of α,ω-alkanedithiols in different ratios with regards to the starting 3-bromocoumarin. The transformation seems to proceed through the DABCO-mediated thia-Michael stereoselective addition of the thiolate anion to the α,β-unsaturated carbonyl system of the coumarin, followed by a DABCO-assisted stereoselective dehydrobromination of the resulting α-bromo carbonyl intermediate.
Fil: Mostardeiro, Vitor B.. Universidade Federal de Santa Maria; Brasil
Fil: Dilelio, Marina C.. Universidade Federal de Santa Maria; 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: Silveira, Claudio. Universidade Federal de Santa Maria; Brasil
description A facile and efficient protocol for the highly selective direct sulfanylation of 3-bromocoumarins under DABCO promotion, was developed. The transformation took place with aromatic and aliphatic thiols as well as with α,ω-dithiols, affording the expected products in very good to excellent yields. Simple and convenient ways to access 4-((ω-mercaptoalkyl) thio)coumarins and the dimeric 4,4′-(alkane-1,4-diylbis(sulfanediyl))bis(coumarins) were also devised with the use of α,ω-alkanedithiols in different ratios with regards to the starting 3-bromocoumarin. The transformation seems to proceed through the DABCO-mediated thia-Michael stereoselective addition of the thiolate anion to the α,β-unsaturated carbonyl system of the coumarin, followed by a DABCO-assisted stereoselective dehydrobromination of the resulting α-bromo carbonyl intermediate.
publishDate 2020
dc.date.none.fl_str_mv 2020-01
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/11336/128127
Mostardeiro, Vitor B.; Dilelio, Marina C.; Kaufman, Teodoro Saul; Silveira, Claudio; Efficient synthesis of 4-sulfanylcoumarins from 3-bromo-coumarins: Via a highly selective DABCO-mediated one-pot thia-Michael addition/elimination process; Royal Society of Chemistry; RSC Advances; 10; 1; 1-2020; 482-491
2046-2069
CONICET Digital
CONICET
url http://hdl.handle.net/11336/128127
identifier_str_mv Mostardeiro, Vitor B.; Dilelio, Marina C.; Kaufman, Teodoro Saul; Silveira, Claudio; Efficient synthesis of 4-sulfanylcoumarins from 3-bromo-coumarins: Via a highly selective DABCO-mediated one-pot thia-Michael addition/elimination process; Royal Society of Chemistry; RSC Advances; 10; 1; 1-2020; 482-491
2046-2069
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://pubs.rsc.org/en/content/articlelanding/2020/ra/c9ra09545d#!divAbstract
info:eu-repo/semantics/altIdentifier/doi/10.1039/C9RA09545D
dc.rights.none.fl_str_mv info:eu-repo/semantics/openAccess
https://creativecommons.org/licenses/by-nc/2.5/ar/
eu_rights_str_mv openAccess
rights_invalid_str_mv https://creativecommons.org/licenses/by-nc/2.5/ar/
dc.format.none.fl_str_mv application/pdf
application/pdf
dc.publisher.none.fl_str_mv Royal Society of Chemistry
publisher.none.fl_str_mv Royal Society of Chemistry
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 12.982451

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