Heteroannulation Reaction of α-Aminoketones for the Efficient Synthesis of 4-Imidazolin-2-ones and 2-Thiones
Autor(a) principal: | |
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Data de Publicação: | 2022 |
Outros Autores: | , , , , , , , , , |
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=S0103-50532022000100013 |
Resumo: | The hydrogenation of α-oximinoketones in methanol/HCl afforded α-aminoketones, which were applied without purification to the synthesis of 4-imidazolin-2-ones and 2-thiones, including chiral derivatives. The latter two series were obtained in high yields by a heteroannulation reaction of α-aminoketones with isocyanates and isothiocyanates, respectively. A double condensation of the α-aminoketones with two mol equivalents of the isocyanates produced a series of 4,5-dialkyl-N,3-diaryl-2-oxo-2,3-dihydro-1H-imidazole-1-carboxamides. With isothiocyanates, a single condensation reaction furnished a series of 4,5-dialkyl-1-aryl-1H-imidazole-2(3H)-thiones, which underwent alkylation with alkyl halides to form the corresponding 1-aryl-2-thioalkyl-1H imidazoles in high yields. |
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Heteroannulation Reaction of α-Aminoketones for the Efficient Synthesis of 4-Imidazolin-2-ones and 2-Thionesα-oximinoketonesα-aminoketones4-imidazolin-2-ones4-imidazolin-2-thionesheteroannulationThe hydrogenation of α-oximinoketones in methanol/HCl afforded α-aminoketones, which were applied without purification to the synthesis of 4-imidazolin-2-ones and 2-thiones, including chiral derivatives. The latter two series were obtained in high yields by a heteroannulation reaction of α-aminoketones with isocyanates and isothiocyanates, respectively. A double condensation of the α-aminoketones with two mol equivalents of the isocyanates produced a series of 4,5-dialkyl-N,3-diaryl-2-oxo-2,3-dihydro-1H-imidazole-1-carboxamides. With isothiocyanates, a single condensation reaction furnished a series of 4,5-dialkyl-1-aryl-1H-imidazole-2(3H)-thiones, which underwent alkylation with alkyl halides to form the corresponding 1-aryl-2-thioalkyl-1H imidazoles in high yields.Sociedade Brasileira de Química2022-01-01info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersiontext/htmlhttp://old.scielo.br/scielo.php?script=sci_arttext&pid=S0103-50532022000100013Journal of the Brazilian Chemical Society v.33 n.1 2022reponame:Journal of the Brazilian Chemical Society (Online)instname:Sociedade Brasileira de Química (SBQ)instacron:SBQ10.21577/0103-5053.20210120info:eu-repo/semantics/openAccessRebollar,AraceliBautista,RafaelGutiérrez,Rsuini U.Espinoza-Hicks,CarlosMendieta,AarónZárate-Zárate,DanielMartínez-Mora,Eder I.Labarrios-Morán,Ehecatl M.Vázquez,Miguel A.Delgado,FranciscoTamariz,Joaquíneng2022-01-06T00:00:00Zoai:scielo:S0103-50532022000100013Revistahttp://jbcs.sbq.org.brONGhttps://old.scielo.br/oai/scielo-oai.php||office@jbcs.sbq.org.br1678-47900103-5053opendoar:2022-01-06T00:00Journal of the Brazilian Chemical Society (Online) - Sociedade Brasileira de Química (SBQ)false |
dc.title.none.fl_str_mv |
Heteroannulation Reaction of α-Aminoketones for the Efficient Synthesis of 4-Imidazolin-2-ones and 2-Thiones |
title |
Heteroannulation Reaction of α-Aminoketones for the Efficient Synthesis of 4-Imidazolin-2-ones and 2-Thiones |
spellingShingle |
Heteroannulation Reaction of α-Aminoketones for the Efficient Synthesis of 4-Imidazolin-2-ones and 2-Thiones Rebollar,Araceli α-oximinoketones α-aminoketones 4-imidazolin-2-ones 4-imidazolin-2-thiones heteroannulation |
title_short |
Heteroannulation Reaction of α-Aminoketones for the Efficient Synthesis of 4-Imidazolin-2-ones and 2-Thiones |
title_full |
Heteroannulation Reaction of α-Aminoketones for the Efficient Synthesis of 4-Imidazolin-2-ones and 2-Thiones |
title_fullStr |
Heteroannulation Reaction of α-Aminoketones for the Efficient Synthesis of 4-Imidazolin-2-ones and 2-Thiones |
title_full_unstemmed |
Heteroannulation Reaction of α-Aminoketones for the Efficient Synthesis of 4-Imidazolin-2-ones and 2-Thiones |
title_sort |
Heteroannulation Reaction of α-Aminoketones for the Efficient Synthesis of 4-Imidazolin-2-ones and 2-Thiones |
author |
Rebollar,Araceli |
author_facet |
Rebollar,Araceli Bautista,Rafael Gutiérrez,Rsuini U. Espinoza-Hicks,Carlos Mendieta,Aarón Zárate-Zárate,Daniel Martínez-Mora,Eder I. Labarrios-Morán,Ehecatl M. Vázquez,Miguel A. Delgado,Francisco Tamariz,Joaquín |
author_role |
author |
author2 |
Bautista,Rafael Gutiérrez,Rsuini U. Espinoza-Hicks,Carlos Mendieta,Aarón Zárate-Zárate,Daniel Martínez-Mora,Eder I. Labarrios-Morán,Ehecatl M. Vázquez,Miguel A. Delgado,Francisco Tamariz,Joaquín |
author2_role |
author author author author author author author author author author |
dc.contributor.author.fl_str_mv |
Rebollar,Araceli Bautista,Rafael Gutiérrez,Rsuini U. Espinoza-Hicks,Carlos Mendieta,Aarón Zárate-Zárate,Daniel Martínez-Mora,Eder I. Labarrios-Morán,Ehecatl M. Vázquez,Miguel A. Delgado,Francisco Tamariz,Joaquín |
dc.subject.por.fl_str_mv |
α-oximinoketones α-aminoketones 4-imidazolin-2-ones 4-imidazolin-2-thiones heteroannulation |
topic |
α-oximinoketones α-aminoketones 4-imidazolin-2-ones 4-imidazolin-2-thiones heteroannulation |
description |
The hydrogenation of α-oximinoketones in methanol/HCl afforded α-aminoketones, which were applied without purification to the synthesis of 4-imidazolin-2-ones and 2-thiones, including chiral derivatives. The latter two series were obtained in high yields by a heteroannulation reaction of α-aminoketones with isocyanates and isothiocyanates, respectively. A double condensation of the α-aminoketones with two mol equivalents of the isocyanates produced a series of 4,5-dialkyl-N,3-diaryl-2-oxo-2,3-dihydro-1H-imidazole-1-carboxamides. With isothiocyanates, a single condensation reaction furnished a series of 4,5-dialkyl-1-aryl-1H-imidazole-2(3H)-thiones, which underwent alkylation with alkyl halides to form the corresponding 1-aryl-2-thioalkyl-1H imidazoles in high yields. |
publishDate |
2022 |
dc.date.none.fl_str_mv |
2022-01-01 |
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=S0103-50532022000100013 |
url |
http://old.scielo.br/scielo.php?script=sci_arttext&pid=S0103-50532022000100013 |
dc.language.iso.fl_str_mv |
eng |
language |
eng |
dc.relation.none.fl_str_mv |
10.21577/0103-5053.20210120 |
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.33 n.1 2022 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 |
_version_ |
1750318184764801024 |