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dc.contributor.author
Mostardeiro, Vitor B.
dc.contributor.author
Dilelio, Marina C.
dc.contributor.author
Kaufman, Teodoro Saul
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dc.contributor.author
Silveira, Claudio
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dc.date.available
2021-03-11T20:08:41Z
dc.date.issued
2020-01
dc.identifier.citation
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
dc.identifier.issn
2046-2069
dc.identifier.uri
http://hdl.handle.net/11336/128127
dc.description.abstract
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.
dc.format
application/pdf
dc.language.iso
eng
dc.publisher
Royal Society of Chemistry
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dc.rights
info:eu-repo/semantics/openAccess
dc.rights.uri
https://creativecommons.org/licenses/by-nc/2.5/ar/
dc.subject
4-thiocoumarins
dc.subject
3-bromocoumarins
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DABCO
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Selective reaction
dc.subject.classification
Química Orgánica
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dc.subject.classification
Ciencias Químicas
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dc.subject.classification
CIENCIAS NATURALES Y EXACTAS
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dc.title
Efficient synthesis of 4-sulfanylcoumarins from 3-bromo-coumarins: Via a highly selective DABCO-mediated one-pot thia-Michael addition/elimination process
dc.type
info:eu-repo/semantics/article
dc.type
info:ar-repo/semantics/artículo
dc.type
info:eu-repo/semantics/publishedVersion
dc.date.updated
2020-06-23T15:13:11Z
dc.journal.volume
10
dc.journal.number
1
dc.journal.pagination
482-491
dc.journal.pais
Reino Unido
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dc.journal.ciudad
Londres
dc.description.fil
Fil: Mostardeiro, Vitor B.. Universidade Federal de Santa Maria; Brasil
dc.description.fil
Fil: Dilelio, Marina C.. Universidade Federal de Santa Maria; Brasil
dc.description.fil
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
dc.description.fil
Fil: Silveira, Claudio. Universidade Federal de Santa Maria; Brasil
dc.journal.title
RSC Advances
dc.relation.alternativeid
info:eu-repo/semantics/altIdentifier/url/https://pubs.rsc.org/en/content/articlelanding/2020/ra/c9ra09545d#!divAbstract
dc.relation.alternativeid
info:eu-repo/semantics/altIdentifier/doi/http://dx.doi.org/10.1039/C9RA09545D
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