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
- Institución
- Consejo Nacional de Investigaciones Científicas y Técnicas
- OAI Identificador
- oai:ri.conicet.gov.ar:11336/128127
Ver los metadatos del registro completo
id |
CONICETDig_a681994b91a86eb49efed8ae19be8a41 |
---|---|
oai_identifier_str |
oai:ri.conicet.gov.ar:11336/128127 |
network_acronym_str |
CONICETDig |
repository_id_str |
3498 |
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 Técnicas2025-09-29T09:48:07Zoai: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:34982025-09-29 09:48:08.095CONICET 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 |
_version_ |
1844613496972509184 |
score |
13.070432 |