Synthesis of a Small Library of Imidazolidin-2-ones using Gold Catalysis on Solid Phase

Autores
la Venia, Agustina; Medran, Noelia Soledad; Krchnak, Viktor; Testero, Sebastian Andres
Año de publicación
2016
Idioma
inglés
Tipo de recurso
artículo
Estado
versión publicada
Descripción
An efficient and high-yielding solid phase synthesis of a small library of imidazolidin-2-ones and imidazol-2-ones was carried out employing a high chemo- and regioselective gold-catalyzed cycloisomerization as a key step. Polymer-supported amino acids derivatized with several alkyne functionalities combined with tosyl- and phenylureas have been subjected to gold-catalysis exhibiting exclusively C-N bond formation. The present work proves the potential of solid phase synthesis and homogeneous gold catalysis as an efficient and powerful synthetic tool for the generation of drug-like heterocycles.
Fil: la Venia, Agustina. 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. Palacky University; República Checa
Fil: Medran, Noelia Soledad. 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
Fil: Krchnak, Viktor. Palacky University; República Checa. University of Notre Dame-Indiana; Estados Unidos
Fil: Testero, Sebastian Andres. 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
Materia
C-N BOND FORMATION
GOLD CATALYSIS
IMIDAZOLIDIN-2-ONES
PROPARGYLUREAS
SOLID-PHASE SYNTHESIS
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:11336/61034
Acceder
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network_acronym_str CONICETDig
repository_id_str 3498
network_name_str CONICET Digital (CONICET)
spelling Synthesis of a Small Library of Imidazolidin-2-ones using Gold Catalysis on Solid Phasela Venia, AgustinaMedran, Noelia SoledadKrchnak, ViktorTestero, Sebastian AndresC-N BOND FORMATIONGOLD CATALYSISIMIDAZOLIDIN-2-ONESPROPARGYLUREASSOLID-PHASE SYNTHESIShttps://purl.org/becyt/ford/1.4https://purl.org/becyt/ford/1An efficient and high-yielding solid phase synthesis of a small library of imidazolidin-2-ones and imidazol-2-ones was carried out employing a high chemo- and regioselective gold-catalyzed cycloisomerization as a key step. Polymer-supported amino acids derivatized with several alkyne functionalities combined with tosyl- and phenylureas have been subjected to gold-catalysis exhibiting exclusively C-N bond formation. The present work proves the potential of solid phase synthesis and homogeneous gold catalysis as an efficient and powerful synthetic tool for the generation of drug-like heterocycles.Fil: la Venia, Agustina. 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. Palacky University; República ChecaFil: Medran, Noelia Soledad. 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; ArgentinaFil: Krchnak, Viktor. Palacky University; República Checa. University of Notre Dame-Indiana; Estados UnidosFil: Testero, Sebastian Andres. 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; ArgentinaAmerican Chemical Society2016-08info: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/11336/61034la Venia, Agustina; Medran, Noelia Soledad; Krchnak, Viktor; Testero, Sebastian Andres; Synthesis of a Small Library of Imidazolidin-2-ones using Gold Catalysis on Solid Phase; American Chemical Society; ACS Combinatorial Science; 18; 8; 8-2016; 482-4892156-8952CONICET DigitalCONICETenginfo:eu-repo/semantics/altIdentifier/url/http://pubs.acs.org/doi/abs/10.1021/acscombsci.6b00062info:eu-repo/semantics/altIdentifier/doi/10.1021/acscombsci.6b00062info:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by-nc-sa/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2025-09-29T10:21:06Zoai:ri.conicet.gov.ar:11336/61034instacron: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:34982025-09-29 10:21:06.907CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse
dc.title.none.fl_str_mv Synthesis of a Small Library of Imidazolidin-2-ones using Gold Catalysis on Solid Phase
title Synthesis of a Small Library of Imidazolidin-2-ones using Gold Catalysis on Solid Phase
spellingShingle Synthesis of a Small Library of Imidazolidin-2-ones using Gold Catalysis on Solid Phase
la Venia, Agustina
C-N BOND FORMATION
GOLD CATALYSIS
IMIDAZOLIDIN-2-ONES
PROPARGYLUREAS
SOLID-PHASE SYNTHESIS
title_short Synthesis of a Small Library of Imidazolidin-2-ones using Gold Catalysis on Solid Phase
title_full Synthesis of a Small Library of Imidazolidin-2-ones using Gold Catalysis on Solid Phase
title_fullStr Synthesis of a Small Library of Imidazolidin-2-ones using Gold Catalysis on Solid Phase
title_full_unstemmed Synthesis of a Small Library of Imidazolidin-2-ones using Gold Catalysis on Solid Phase
title_sort Synthesis of a Small Library of Imidazolidin-2-ones using Gold Catalysis on Solid Phase
dc.creator.none.fl_str_mv la Venia, Agustina
Medran, Noelia Soledad
Krchnak, Viktor
Testero, Sebastian Andres
author la Venia, Agustina
author_facet la Venia, Agustina
Medran, Noelia Soledad
Krchnak, Viktor
Testero, Sebastian Andres
author_role author
author2 Medran, Noelia Soledad
Krchnak, Viktor
Testero, Sebastian Andres
author2_role author
author
author
dc.subject.none.fl_str_mv C-N BOND FORMATION
GOLD CATALYSIS
IMIDAZOLIDIN-2-ONES
PROPARGYLUREAS
SOLID-PHASE SYNTHESIS
topic C-N BOND FORMATION
GOLD CATALYSIS
IMIDAZOLIDIN-2-ONES
PROPARGYLUREAS
SOLID-PHASE SYNTHESIS
purl_subject.fl_str_mv https://purl.org/becyt/ford/1.4
https://purl.org/becyt/ford/1
dc.description.none.fl_txt_mv An efficient and high-yielding solid phase synthesis of a small library of imidazolidin-2-ones and imidazol-2-ones was carried out employing a high chemo- and regioselective gold-catalyzed cycloisomerization as a key step. Polymer-supported amino acids derivatized with several alkyne functionalities combined with tosyl- and phenylureas have been subjected to gold-catalysis exhibiting exclusively C-N bond formation. The present work proves the potential of solid phase synthesis and homogeneous gold catalysis as an efficient and powerful synthetic tool for the generation of drug-like heterocycles.
Fil: la Venia, Agustina. 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. Palacky University; República Checa
Fil: Medran, Noelia Soledad. 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
Fil: Krchnak, Viktor. Palacky University; República Checa. University of Notre Dame-Indiana; Estados Unidos
Fil: Testero, Sebastian Andres. 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
description An efficient and high-yielding solid phase synthesis of a small library of imidazolidin-2-ones and imidazol-2-ones was carried out employing a high chemo- and regioselective gold-catalyzed cycloisomerization as a key step. Polymer-supported amino acids derivatized with several alkyne functionalities combined with tosyl- and phenylureas have been subjected to gold-catalysis exhibiting exclusively C-N bond formation. The present work proves the potential of solid phase synthesis and homogeneous gold catalysis as an efficient and powerful synthetic tool for the generation of drug-like heterocycles.
publishDate 2016
dc.date.none.fl_str_mv 2016-08
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/11336/61034
la Venia, Agustina; Medran, Noelia Soledad; Krchnak, Viktor; Testero, Sebastian Andres; Synthesis of a Small Library of Imidazolidin-2-ones using Gold Catalysis on Solid Phase; American Chemical Society; ACS Combinatorial Science; 18; 8; 8-2016; 482-489
2156-8952
CONICET Digital
CONICET
url http://hdl.handle.net/11336/61034
identifier_str_mv la Venia, Agustina; Medran, Noelia Soledad; Krchnak, Viktor; Testero, Sebastian Andres; Synthesis of a Small Library of Imidazolidin-2-ones using Gold Catalysis on Solid Phase; American Chemical Society; ACS Combinatorial Science; 18; 8; 8-2016; 482-489
2156-8952
CONICET Digital
CONICET
dc.language.none.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv info:eu-repo/semantics/altIdentifier/url/http://pubs.acs.org/doi/abs/10.1021/acscombsci.6b00062
info:eu-repo/semantics/altIdentifier/doi/10.1021/acscombsci.6b00062
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 American Chemical Society
publisher.none.fl_str_mv American Chemical Society
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
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score 13.070432

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