Cargando…

Decarboxylative ring-opening of 2-oxazolidinones: a facile and modular synthesis of β-chalcogen amines

We report herein the synthesis of primary and secondary β-chalcogen amines through the regioselective ring-opening reaction of non-activated 2-oxazolidinones promoted by in situ generated chalcogenolate anions. The developed one-step protocol enabled the preparation of β-selenoamines, β-telluroamine...

Descripción completa

Detalles Bibliográficos
Autores principales: Galetto, Fábio Z., da Silva, Cleiton, Beche, Ricardo I. M., Balaguez, Renata A., Franco, Marcelo S., de Assis, Francisco F., Frizon, Tiago E. A., Su, Xiao
Formato: Online Artículo Texto
Lenguaje:English
Publicado: The Royal Society of Chemistry 2022
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9710311/
https://www.ncbi.nlm.nih.gov/pubmed/36545628
http://dx.doi.org/10.1039/d2ra06070a
_version_ 1784841337464422400
author Galetto, Fábio Z.
da Silva, Cleiton
Beche, Ricardo I. M.
Balaguez, Renata A.
Franco, Marcelo S.
de Assis, Francisco F.
Frizon, Tiago E. A.
Su, Xiao
author_facet Galetto, Fábio Z.
da Silva, Cleiton
Beche, Ricardo I. M.
Balaguez, Renata A.
Franco, Marcelo S.
de Assis, Francisco F.
Frizon, Tiago E. A.
Su, Xiao
author_sort Galetto, Fábio Z.
collection PubMed
description We report herein the synthesis of primary and secondary β-chalcogen amines through the regioselective ring-opening reaction of non-activated 2-oxazolidinones promoted by in situ generated chalcogenolate anions. The developed one-step protocol enabled the preparation of β-selenoamines, β-telluroamines and β-thioamines with appreciable structural diversity and in yields of up to 95%.
format Online
Article
Text
id pubmed-9710311
institution National Center for Biotechnology Information
language English
publishDate 2022
publisher The Royal Society of Chemistry
record_format MEDLINE/PubMed
spelling pubmed-97103112022-12-20 Decarboxylative ring-opening of 2-oxazolidinones: a facile and modular synthesis of β-chalcogen amines Galetto, Fábio Z. da Silva, Cleiton Beche, Ricardo I. M. Balaguez, Renata A. Franco, Marcelo S. de Assis, Francisco F. Frizon, Tiago E. A. Su, Xiao RSC Adv Chemistry We report herein the synthesis of primary and secondary β-chalcogen amines through the regioselective ring-opening reaction of non-activated 2-oxazolidinones promoted by in situ generated chalcogenolate anions. The developed one-step protocol enabled the preparation of β-selenoamines, β-telluroamines and β-thioamines with appreciable structural diversity and in yields of up to 95%. The Royal Society of Chemistry 2022-11-30 /pmc/articles/PMC9710311/ /pubmed/36545628 http://dx.doi.org/10.1039/d2ra06070a Text en This journal is © The Royal Society of Chemistry https://creativecommons.org/licenses/by-nc/3.0/
spellingShingle Chemistry
Galetto, Fábio Z.
da Silva, Cleiton
Beche, Ricardo I. M.
Balaguez, Renata A.
Franco, Marcelo S.
de Assis, Francisco F.
Frizon, Tiago E. A.
Su, Xiao
Decarboxylative ring-opening of 2-oxazolidinones: a facile and modular synthesis of β-chalcogen amines
title Decarboxylative ring-opening of 2-oxazolidinones: a facile and modular synthesis of β-chalcogen amines
title_full Decarboxylative ring-opening of 2-oxazolidinones: a facile and modular synthesis of β-chalcogen amines
title_fullStr Decarboxylative ring-opening of 2-oxazolidinones: a facile and modular synthesis of β-chalcogen amines
title_full_unstemmed Decarboxylative ring-opening of 2-oxazolidinones: a facile and modular synthesis of β-chalcogen amines
title_short Decarboxylative ring-opening of 2-oxazolidinones: a facile and modular synthesis of β-chalcogen amines
title_sort decarboxylative ring-opening of 2-oxazolidinones: a facile and modular synthesis of β-chalcogen amines
topic Chemistry
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9710311/
https://www.ncbi.nlm.nih.gov/pubmed/36545628
http://dx.doi.org/10.1039/d2ra06070a
work_keys_str_mv AT galettofabioz decarboxylativeringopeningof2oxazolidinonesafacileandmodularsynthesisofbchalcogenamines
AT dasilvacleiton decarboxylativeringopeningof2oxazolidinonesafacileandmodularsynthesisofbchalcogenamines
AT bechericardoim decarboxylativeringopeningof2oxazolidinonesafacileandmodularsynthesisofbchalcogenamines
AT balaguezrenataa decarboxylativeringopeningof2oxazolidinonesafacileandmodularsynthesisofbchalcogenamines
AT francomarcelos decarboxylativeringopeningof2oxazolidinonesafacileandmodularsynthesisofbchalcogenamines
AT deassisfranciscof decarboxylativeringopeningof2oxazolidinonesafacileandmodularsynthesisofbchalcogenamines
AT frizontiagoea decarboxylativeringopeningof2oxazolidinonesafacileandmodularsynthesisofbchalcogenamines
AT suxiao decarboxylativeringopeningof2oxazolidinonesafacileandmodularsynthesisofbchalcogenamines