Selective synthesis using ETFBO: a new strategy for the preparation of hexahydro‐1H‐pyrrolo[1,2‐c]imidazol‐1‐one.

Autores
Faillace, Martín Sebastián; Ceballos, Noelia Marcela; Shustova, Natalia; Peláez, Walter José
Año de publicación
2023
Idioma
inglés
Tipo de recurso
artículo
Estado
versión publicada
Descripción
In this work, we report the regiospecific and stereoselective synthesis of novel pyrrolo thioxoimidazolidinones with promising biological activities due to the inherent pharmaceutical properties of thioxoimidazolidinone core. The reaction of different thioxoimidazolidinones with trans-4-ethoxy-1,1,1-trifluorobut-3-en-2-one (ETFBO) yields bicyclic 1,3-diaza heterocycles bearing the trifluoromethyl (CF3) moiety. Our investigation involved both depth experimental analysis and theoretical calculations to fathom out the mode of reaction of this building block and elucidate the underlying mechanism operating for the observed reactions. Remarkably, this unusual mechanism retained the ethanol moiety from the building block in the final products, deviating from conventional nucleophilic reactions reported in the literature.
Fil: Faillace, Martín Sebastián. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Córdoba. Instituto de Investigaciones en Físico-química de Córdoba. Universidad Nacional de Córdoba. Facultad de Ciencias Químicas. Instituto de Investigaciones en Físico-química de Córdoba; Argentina
Fil: Ceballos, Noelia Marcela. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Córdoba. Instituto de Investigaciones en Físico-química de Córdoba. Universidad Nacional de Córdoba. Facultad de Ciencias Químicas. Instituto de Investigaciones en Físico-química de Córdoba; Argentina
Fil: Shustova, Natalia. University Of South Carolina; Estados Unidos
Fil: Peláez, Walter José. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Córdoba. Instituto de Investigaciones en Físico-química de Córdoba. Universidad Nacional de Córdoba. Facultad de Ciencias Químicas. Instituto de Investigaciones en Físico-química de Córdoba; Argentina
Materia
Annulation
Microwave Chemistry
Nitrogen Heterocycles
Thioxoimidazolidinone
Trifluoromethyl
Nivel de accesibilidad
acceso abierto
Condiciones de uso
https://creativecommons.org/licenses/by-nc-sa/2.5/ar/
Repositorio
CONICET Digital (CONICET)
Institución
Consejo Nacional de Investigaciones Científicas y Técnicas
OAI Identificador
oai:ri.conicet.gov.ar:11336/226847
Acceder
id CONICETDig_898a3789ab28c07e4e113b14cd93c630
oai_identifier_str oai:ri.conicet.gov.ar:11336/226847
network_acronym_str CONICETDig
repository_id_str 3498
network_name_str CONICET Digital (CONICET)
spelling Selective synthesis using ETFBO: a new strategy for the preparation of hexahydro‐1H‐pyrrolo[1,2‐c]imidazol‐1‐one.Faillace, Martín SebastiánCeballos, Noelia MarcelaShustova, NataliaPeláez, Walter JoséAnnulationMicrowave ChemistryNitrogen HeterocyclesThioxoimidazolidinoneTrifluoromethylhttps://purl.org/becyt/ford/1.4https://purl.org/becyt/ford/1In this work, we report the regiospecific and stereoselective synthesis of novel pyrrolo thioxoimidazolidinones with promising biological activities due to the inherent pharmaceutical properties of thioxoimidazolidinone core. The reaction of different thioxoimidazolidinones with trans-4-ethoxy-1,1,1-trifluorobut-3-en-2-one (ETFBO) yields bicyclic 1,3-diaza heterocycles bearing the trifluoromethyl (CF3) moiety. Our investigation involved both depth experimental analysis and theoretical calculations to fathom out the mode of reaction of this building block and elucidate the underlying mechanism operating for the observed reactions. Remarkably, this unusual mechanism retained the ethanol moiety from the building block in the final products, deviating from conventional nucleophilic reactions reported in the literature.Fil: Faillace, Martín Sebastián. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Córdoba. Instituto de Investigaciones en Físico-química de Córdoba. Universidad Nacional de Córdoba. Facultad de Ciencias Químicas. Instituto de Investigaciones en Físico-química de Córdoba; ArgentinaFil: Ceballos, Noelia Marcela. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Córdoba. Instituto de Investigaciones en Físico-química de Córdoba. Universidad Nacional de Córdoba. Facultad de Ciencias Químicas. Instituto de Investigaciones en Físico-química de Córdoba; ArgentinaFil: Shustova, Natalia. University Of South Carolina; Estados UnidosFil: Peláez, Walter José. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Córdoba. Instituto de Investigaciones en Físico-química de Córdoba. Universidad Nacional de Córdoba. Facultad de Ciencias Químicas. Instituto de Investigaciones en Físico-química de Córdoba; ArgentinaJohn Wiley & Sons2023-07info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionhttp://purl.org/coar/resource_type/c_6501info:ar-repo/semantics/articuloapplication/pdfapplication/pdfapplication/pdfhttp://hdl.handle.net/11336/226847Faillace, Martín Sebastián; Ceballos, Noelia Marcela; Shustova, Natalia; Peláez, Walter José; Selective synthesis using ETFBO: a new strategy for the preparation of hexahydro‐1H‐pyrrolo[1,2‐c]imidazol‐1‐one.; John Wiley & Sons; Asian Journal of Organic Chemistry; 12; 8; 7-2023; 1-162193-5807CONICET DigitalCONICETenginfo:eu-repo/semantics/altIdentifier/url/https://onlinelibrary.wiley.com/doi/10.1002/ajoc.202300318info:eu-repo/semantics/altIdentifier/doi/10.1002/ajoc.202300318info:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by-nc-sa/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2025-09-17T10:52:41Zoai:ri.conicet.gov.ar:11336/226847instacron: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:34982025-09-17 10:52:41.528CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse
dc.title.none.fl_str_mv Selective synthesis using ETFBO: a new strategy for the preparation of hexahydro‐1H‐pyrrolo[1,2‐c]imidazol‐1‐one.
title Selective synthesis using ETFBO: a new strategy for the preparation of hexahydro‐1H‐pyrrolo[1,2‐c]imidazol‐1‐one.
spellingShingle Selective synthesis using ETFBO: a new strategy for the preparation of hexahydro‐1H‐pyrrolo[1,2‐c]imidazol‐1‐one.
Faillace, Martín Sebastián
Annulation
Microwave Chemistry
Nitrogen Heterocycles
Thioxoimidazolidinone
Trifluoromethyl
title_short Selective synthesis using ETFBO: a new strategy for the preparation of hexahydro‐1H‐pyrrolo[1,2‐c]imidazol‐1‐one.
title_full Selective synthesis using ETFBO: a new strategy for the preparation of hexahydro‐1H‐pyrrolo[1,2‐c]imidazol‐1‐one.
title_fullStr Selective synthesis using ETFBO: a new strategy for the preparation of hexahydro‐1H‐pyrrolo[1,2‐c]imidazol‐1‐one.
title_full_unstemmed Selective synthesis using ETFBO: a new strategy for the preparation of hexahydro‐1H‐pyrrolo[1,2‐c]imidazol‐1‐one.
title_sort Selective synthesis using ETFBO: a new strategy for the preparation of hexahydro‐1H‐pyrrolo[1,2‐c]imidazol‐1‐one.
dc.creator.none.fl_str_mv Faillace, Martín Sebastián
Ceballos, Noelia Marcela
Shustova, Natalia
Peláez, Walter José
author Faillace, Martín Sebastián
author_facet Faillace, Martín Sebastián
Ceballos, Noelia Marcela
Shustova, Natalia
Peláez, Walter José
author_role author
author2 Ceballos, Noelia Marcela
Shustova, Natalia
Peláez, Walter José
author2_role author
author
author
dc.subject.none.fl_str_mv Annulation
Microwave Chemistry
Nitrogen Heterocycles
Thioxoimidazolidinone
Trifluoromethyl
topic Annulation
Microwave Chemistry
Nitrogen Heterocycles
Thioxoimidazolidinone
Trifluoromethyl
purl_subject.fl_str_mv https://purl.org/becyt/ford/1.4
https://purl.org/becyt/ford/1
dc.description.none.fl_txt_mv In this work, we report the regiospecific and stereoselective synthesis of novel pyrrolo thioxoimidazolidinones with promising biological activities due to the inherent pharmaceutical properties of thioxoimidazolidinone core. The reaction of different thioxoimidazolidinones with trans-4-ethoxy-1,1,1-trifluorobut-3-en-2-one (ETFBO) yields bicyclic 1,3-diaza heterocycles bearing the trifluoromethyl (CF3) moiety. Our investigation involved both depth experimental analysis and theoretical calculations to fathom out the mode of reaction of this building block and elucidate the underlying mechanism operating for the observed reactions. Remarkably, this unusual mechanism retained the ethanol moiety from the building block in the final products, deviating from conventional nucleophilic reactions reported in the literature.
Fil: Faillace, Martín Sebastián. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Córdoba. Instituto de Investigaciones en Físico-química de Córdoba. Universidad Nacional de Córdoba. Facultad de Ciencias Químicas. Instituto de Investigaciones en Físico-química de Córdoba; Argentina
Fil: Ceballos, Noelia Marcela. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Córdoba. Instituto de Investigaciones en Físico-química de Córdoba. Universidad Nacional de Córdoba. Facultad de Ciencias Químicas. Instituto de Investigaciones en Físico-química de Córdoba; Argentina
Fil: Shustova, Natalia. University Of South Carolina; Estados Unidos
Fil: Peláez, Walter José. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Córdoba. Instituto de Investigaciones en Físico-química de Córdoba. Universidad Nacional de Córdoba. Facultad de Ciencias Químicas. Instituto de Investigaciones en Físico-química de Córdoba; Argentina
description In this work, we report the regiospecific and stereoselective synthesis of novel pyrrolo thioxoimidazolidinones with promising biological activities due to the inherent pharmaceutical properties of thioxoimidazolidinone core. The reaction of different thioxoimidazolidinones with trans-4-ethoxy-1,1,1-trifluorobut-3-en-2-one (ETFBO) yields bicyclic 1,3-diaza heterocycles bearing the trifluoromethyl (CF3) moiety. Our investigation involved both depth experimental analysis and theoretical calculations to fathom out the mode of reaction of this building block and elucidate the underlying mechanism operating for the observed reactions. Remarkably, this unusual mechanism retained the ethanol moiety from the building block in the final products, deviating from conventional nucleophilic reactions reported in the literature.
publishDate 2023
dc.date.none.fl_str_mv 2023-07
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/11336/226847
Faillace, Martín Sebastián; Ceballos, Noelia Marcela; Shustova, Natalia; Peláez, Walter José; Selective synthesis using ETFBO: a new strategy for the preparation of hexahydro‐1H‐pyrrolo[1,2‐c]imidazol‐1‐one.; John Wiley & Sons; Asian Journal of Organic Chemistry; 12; 8; 7-2023; 1-16
2193-5807
CONICET Digital
CONICET
url http://hdl.handle.net/11336/226847
identifier_str_mv Faillace, Martín Sebastián; Ceballos, Noelia Marcela; Shustova, Natalia; Peláez, Walter José; Selective synthesis using ETFBO: a new strategy for the preparation of hexahydro‐1H‐pyrrolo[1,2‐c]imidazol‐1‐one.; John Wiley & Sons; Asian Journal of Organic Chemistry; 12; 8; 7-2023; 1-16
2193-5807
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://onlinelibrary.wiley.com/doi/10.1002/ajoc.202300318
info:eu-repo/semantics/altIdentifier/doi/10.1002/ajoc.202300318
dc.rights.none.fl_str_mv info:eu-repo/semantics/openAccess
https://creativecommons.org/licenses/by-nc-sa/2.5/ar/
eu_rights_str_mv openAccess
rights_invalid_str_mv https://creativecommons.org/licenses/by-nc-sa/2.5/ar/
dc.format.none.fl_str_mv application/pdf
application/pdf
application/pdf
dc.publisher.none.fl_str_mv John Wiley & Sons
publisher.none.fl_str_mv John Wiley & Sons
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_ 1843606161975148544
score 13.001348

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