Elemental Chalcogen (Se, S) in PEG-400 to the Synthesis of Seleno- and Thioflavones from 2-Chlorophenyl Ethynyl Ketone and Nucleophilic Species of Chalcogen

Detalhes bibliográficos
Autor(a) principal: Nobre,Patrick C.
Data de Publicação: 2021
Outros Autores: Peglow,Thiago J., Bartz,Ricardo H., Barcellos,Angelita M., Jacob,Raquel G., Silva,Márcio S., Barcellos,Thiago, Perin,Gelson
Tipo de documento: Artigo
Idioma: eng
Título da fonte: Journal of the Brazilian Chemical Society (Online)
Texto Completo: http://old.scielo.br/scielo.php?script=sci_arttext&pid=S0103-50532021000801541
Resumo: An alternative green method was developed for the synthesis of thio-and selenoflavones by the ring closure of 2-chlorophenyl ethynyl ketone with NaHY (Y = S, Se). These nucleophilic chalcogen species were generated in situ using NaBH4 to reduce the elemental chalcogen in the presence of polyethylene glycol-400 (PEG-400). The efficiency of this reaction is strongly dependent on the PEG-400 solvent, acting like a crown ether, complexing with the sodium atom of NaHY species, making the chalcogen nucleophile more active. The synthetic protocol proceeded efficiently at 100 °C under argon, using a range of 2-chlorophenyl ethynyl ketone containing alkyl, aryl, or vinyl groups and the sulfur and selenium chalcogen. By this efficient and simple approach, 18 chalcogenoflavones were obtained in good to excellent yields after 2 h.
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spelling Elemental Chalcogen (Se, S) in PEG-400 to the Synthesis of Seleno- and Thioflavones from 2-Chlorophenyl Ethynyl Ketone and Nucleophilic Species of Chalcogenchromonegreen chemistrypolyethyelene glycol-400seleniumsulfurAn alternative green method was developed for the synthesis of thio-and selenoflavones by the ring closure of 2-chlorophenyl ethynyl ketone with NaHY (Y = S, Se). These nucleophilic chalcogen species were generated in situ using NaBH4 to reduce the elemental chalcogen in the presence of polyethylene glycol-400 (PEG-400). The efficiency of this reaction is strongly dependent on the PEG-400 solvent, acting like a crown ether, complexing with the sodium atom of NaHY species, making the chalcogen nucleophile more active. The synthetic protocol proceeded efficiently at 100 °C under argon, using a range of 2-chlorophenyl ethynyl ketone containing alkyl, aryl, or vinyl groups and the sulfur and selenium chalcogen. By this efficient and simple approach, 18 chalcogenoflavones were obtained in good to excellent yields after 2 h.Sociedade Brasileira de Química2021-08-01info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersiontext/htmlhttp://old.scielo.br/scielo.php?script=sci_arttext&pid=S0103-50532021000801541Journal of the Brazilian Chemical Society v.32 n.8 2021reponame:Journal of the Brazilian Chemical Society (Online)instname:Sociedade Brasileira de Química (SBQ)instacron:SBQ10.21577/0103-5053.20210051info:eu-repo/semantics/openAccessNobre,Patrick C.Peglow,Thiago J.Bartz,Ricardo H.Barcellos,Angelita M.Jacob,Raquel G.Silva,Márcio S.Barcellos,ThiagoPerin,Gelsoneng2021-07-26T00:00:00Zoai:scielo:S0103-50532021000801541Revistahttp://jbcs.sbq.org.brONGhttps://old.scielo.br/oai/scielo-oai.php||office@jbcs.sbq.org.br1678-47900103-5053opendoar:2021-07-26T00:00Journal of the Brazilian Chemical Society (Online) - Sociedade Brasileira de Química (SBQ)false
dc.title.none.fl_str_mv Elemental Chalcogen (Se, S) in PEG-400 to the Synthesis of Seleno- and Thioflavones from 2-Chlorophenyl Ethynyl Ketone and Nucleophilic Species of Chalcogen
title Elemental Chalcogen (Se, S) in PEG-400 to the Synthesis of Seleno- and Thioflavones from 2-Chlorophenyl Ethynyl Ketone and Nucleophilic Species of Chalcogen
spellingShingle Elemental Chalcogen (Se, S) in PEG-400 to the Synthesis of Seleno- and Thioflavones from 2-Chlorophenyl Ethynyl Ketone and Nucleophilic Species of Chalcogen
Nobre,Patrick C.
chromone
green chemistry
polyethyelene glycol-400
selenium
sulfur
title_short Elemental Chalcogen (Se, S) in PEG-400 to the Synthesis of Seleno- and Thioflavones from 2-Chlorophenyl Ethynyl Ketone and Nucleophilic Species of Chalcogen
title_full Elemental Chalcogen (Se, S) in PEG-400 to the Synthesis of Seleno- and Thioflavones from 2-Chlorophenyl Ethynyl Ketone and Nucleophilic Species of Chalcogen
title_fullStr Elemental Chalcogen (Se, S) in PEG-400 to the Synthesis of Seleno- and Thioflavones from 2-Chlorophenyl Ethynyl Ketone and Nucleophilic Species of Chalcogen
title_full_unstemmed Elemental Chalcogen (Se, S) in PEG-400 to the Synthesis of Seleno- and Thioflavones from 2-Chlorophenyl Ethynyl Ketone and Nucleophilic Species of Chalcogen
title_sort Elemental Chalcogen (Se, S) in PEG-400 to the Synthesis of Seleno- and Thioflavones from 2-Chlorophenyl Ethynyl Ketone and Nucleophilic Species of Chalcogen
author Nobre,Patrick C.
author_facet Nobre,Patrick C.
Peglow,Thiago J.
Bartz,Ricardo H.
Barcellos,Angelita M.
Jacob,Raquel G.
Silva,Márcio S.
Barcellos,Thiago
Perin,Gelson
author_role author
author2 Peglow,Thiago J.
Bartz,Ricardo H.
Barcellos,Angelita M.
Jacob,Raquel G.
Silva,Márcio S.
Barcellos,Thiago
Perin,Gelson
author2_role author
author
author
author
author
author
author
dc.contributor.author.fl_str_mv Nobre,Patrick C.
Peglow,Thiago J.
Bartz,Ricardo H.
Barcellos,Angelita M.
Jacob,Raquel G.
Silva,Márcio S.
Barcellos,Thiago
Perin,Gelson
dc.subject.por.fl_str_mv chromone
green chemistry
polyethyelene glycol-400
selenium
sulfur
topic chromone
green chemistry
polyethyelene glycol-400
selenium
sulfur
description An alternative green method was developed for the synthesis of thio-and selenoflavones by the ring closure of 2-chlorophenyl ethynyl ketone with NaHY (Y = S, Se). These nucleophilic chalcogen species were generated in situ using NaBH4 to reduce the elemental chalcogen in the presence of polyethylene glycol-400 (PEG-400). The efficiency of this reaction is strongly dependent on the PEG-400 solvent, acting like a crown ether, complexing with the sodium atom of NaHY species, making the chalcogen nucleophile more active. The synthetic protocol proceeded efficiently at 100 °C under argon, using a range of 2-chlorophenyl ethynyl ketone containing alkyl, aryl, or vinyl groups and the sulfur and selenium chalcogen. By this efficient and simple approach, 18 chalcogenoflavones were obtained in good to excellent yields after 2 h.
publishDate 2021
dc.date.none.fl_str_mv 2021-08-01
dc.type.driver.fl_str_mv info:eu-repo/semantics/article
dc.type.status.fl_str_mv info:eu-repo/semantics/publishedVersion
format article
status_str publishedVersion
dc.identifier.uri.fl_str_mv http://old.scielo.br/scielo.php?script=sci_arttext&pid=S0103-50532021000801541
url http://old.scielo.br/scielo.php?script=sci_arttext&pid=S0103-50532021000801541
dc.language.iso.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv 10.21577/0103-5053.20210051
dc.rights.driver.fl_str_mv info:eu-repo/semantics/openAccess
eu_rights_str_mv openAccess
dc.format.none.fl_str_mv text/html
dc.publisher.none.fl_str_mv Sociedade Brasileira de Química
publisher.none.fl_str_mv Sociedade Brasileira de Química
dc.source.none.fl_str_mv Journal of the Brazilian Chemical Society v.32 n.8 2021
reponame:Journal of the Brazilian Chemical Society (Online)
instname:Sociedade Brasileira de Química (SBQ)
instacron:SBQ
instname_str Sociedade Brasileira de Química (SBQ)
instacron_str SBQ
institution SBQ
reponame_str Journal of the Brazilian Chemical Society (Online)
collection Journal of the Brazilian Chemical Society (Online)
repository.name.fl_str_mv Journal of the Brazilian Chemical Society (Online) - Sociedade Brasileira de Química (SBQ)
repository.mail.fl_str_mv ||office@jbcs.sbq.org.br
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