CeIII-promoted oxidation: Efficient aerobic one-pot eco-friendly synthesis of oxidized bis(indol-3-yl)methanes and cyclic tetra(indolyl)dimethanes

Autores
Silveira, Claudio C.; Mendes, Samuel R.; Villetti, Marcos A.; Back, Davi F.; Kaufman, Teodoro Saul
Año de publicación
2012
Idioma
inglés
Tipo de recurso
artículo
Estado
versión publicada
Descripción
Indoles and benzaldehyde derivatives undergo an efficient one-pot smooth condensation and a further atmospheric-pressure aerobic dehydrogenation with CeCl3 in i-PrOH, to afford the corresponding oxidized bis(indol-3-yl)methanes. Use of 2,2-bisindole as the heterocyclic precursor provides cyclic tetra(indolyl)dimethane derivatives, which further undergo partial oxidation to the related calix-shaped macrocycles, carrying an all cis 1,3,7-cyclodecatriene core and supporting a 2,2-biindolylidene moiety. The syntheses of these high value-added compounds is operationally simple and can be performed at room temperature under mild, neutral and environmentally friendly conditions.
Fil: Silveira, Claudio C.. Universidade Federal de Santa Maria; Brasil
Fil: Mendes, Samuel R.. Universidade Federal de Santa Catarina; Brasil
Fil: Villetti, Marcos A.. Universidade Federal de Santa Maria; Brasil
Fil: Back, Davi F.. Universidade Federal de Santa Maria; Brasil
Fil: Kaufman, Teodoro Saul. 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
Oxidation
Green Chemistry
Oxidized BIMs
Novel reactions
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:11336/105098
Acceder
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repository_id_str 3498
network_name_str CONICET Digital (CONICET)
spelling CeIII-promoted oxidation: Efficient aerobic one-pot eco-friendly synthesis of oxidized bis(indol-3-yl)methanes and cyclic tetra(indolyl)dimethanesSilveira, Claudio C.Mendes, Samuel R.Villetti, Marcos A.Back, Davi F.Kaufman, Teodoro SaulOxidationGreen ChemistryOxidized BIMsNovel reactionshttps://purl.org/becyt/ford/1.4https://purl.org/becyt/ford/1Indoles and benzaldehyde derivatives undergo an efficient one-pot smooth condensation and a further atmospheric-pressure aerobic dehydrogenation with CeCl3 in i-PrOH, to afford the corresponding oxidized bis(indol-3-yl)methanes. Use of 2,2-bisindole as the heterocyclic precursor provides cyclic tetra(indolyl)dimethane derivatives, which further undergo partial oxidation to the related calix-shaped macrocycles, carrying an all cis 1,3,7-cyclodecatriene core and supporting a 2,2-biindolylidene moiety. The syntheses of these high value-added compounds is operationally simple and can be performed at room temperature under mild, neutral and environmentally friendly conditions.Fil: Silveira, Claudio C.. Universidade Federal de Santa Maria; BrasilFil: Mendes, Samuel R.. Universidade Federal de Santa Catarina; BrasilFil: Villetti, Marcos A.. Universidade Federal de Santa Maria; BrasilFil: Back, Davi F.. Universidade Federal de Santa Maria; BrasilFil: Kaufman, Teodoro Saul. 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; ArgentinaRoyal Society of Chemistry2012-08info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionhttp://purl.org/coar/resource_type/c_6501info:ar-repo/semantics/articuloapplication/pdfapplication/pdfhttp://hdl.handle.net/11336/105098Silveira, Claudio C.; Mendes, Samuel R.; Villetti, Marcos A.; Back, Davi F.; Kaufman, Teodoro Saul; CeIII-promoted oxidation: Efficient aerobic one-pot eco-friendly synthesis of oxidized bis(indol-3-yl)methanes and cyclic tetra(indolyl)dimethanes; Royal Society of Chemistry; Green Chemistry (print); 14; 10; 8-2012; 2912-29211463-9262CONICET DigitalCONICETenginfo:eu-repo/semantics/altIdentifier/url/https://pubs.rsc.org/en/content/articlelanding/2012/GC/c2gc36131k#!divAbstractinfo:eu-repo/semantics/altIdentifier/doi/10.1039/c2gc36131kinfo:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by-nc-sa/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2025-09-10T13:08:05Zoai:ri.conicet.gov.ar:11336/105098instacron: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:34982025-09-10 13:08:05.479CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse
dc.title.none.fl_str_mv CeIII-promoted oxidation: Efficient aerobic one-pot eco-friendly synthesis of oxidized bis(indol-3-yl)methanes and cyclic tetra(indolyl)dimethanes
title CeIII-promoted oxidation: Efficient aerobic one-pot eco-friendly synthesis of oxidized bis(indol-3-yl)methanes and cyclic tetra(indolyl)dimethanes
spellingShingle CeIII-promoted oxidation: Efficient aerobic one-pot eco-friendly synthesis of oxidized bis(indol-3-yl)methanes and cyclic tetra(indolyl)dimethanes
Silveira, Claudio C.
Oxidation
Green Chemistry
Oxidized BIMs
Novel reactions
title_short CeIII-promoted oxidation: Efficient aerobic one-pot eco-friendly synthesis of oxidized bis(indol-3-yl)methanes and cyclic tetra(indolyl)dimethanes
title_full CeIII-promoted oxidation: Efficient aerobic one-pot eco-friendly synthesis of oxidized bis(indol-3-yl)methanes and cyclic tetra(indolyl)dimethanes
title_fullStr CeIII-promoted oxidation: Efficient aerobic one-pot eco-friendly synthesis of oxidized bis(indol-3-yl)methanes and cyclic tetra(indolyl)dimethanes
title_full_unstemmed CeIII-promoted oxidation: Efficient aerobic one-pot eco-friendly synthesis of oxidized bis(indol-3-yl)methanes and cyclic tetra(indolyl)dimethanes
title_sort CeIII-promoted oxidation: Efficient aerobic one-pot eco-friendly synthesis of oxidized bis(indol-3-yl)methanes and cyclic tetra(indolyl)dimethanes
dc.creator.none.fl_str_mv Silveira, Claudio C.
Mendes, Samuel R.
Villetti, Marcos A.
Back, Davi F.
Kaufman, Teodoro Saul
author Silveira, Claudio C.
author_facet Silveira, Claudio C.
Mendes, Samuel R.
Villetti, Marcos A.
Back, Davi F.
Kaufman, Teodoro Saul
author_role author
author2 Mendes, Samuel R.
Villetti, Marcos A.
Back, Davi F.
Kaufman, Teodoro Saul
author2_role author
author
author
author
dc.subject.none.fl_str_mv Oxidation
Green Chemistry
Oxidized BIMs
Novel reactions
topic Oxidation
Green Chemistry
Oxidized BIMs
Novel reactions
purl_subject.fl_str_mv https://purl.org/becyt/ford/1.4
https://purl.org/becyt/ford/1
dc.description.none.fl_txt_mv Indoles and benzaldehyde derivatives undergo an efficient one-pot smooth condensation and a further atmospheric-pressure aerobic dehydrogenation with CeCl3 in i-PrOH, to afford the corresponding oxidized bis(indol-3-yl)methanes. Use of 2,2-bisindole as the heterocyclic precursor provides cyclic tetra(indolyl)dimethane derivatives, which further undergo partial oxidation to the related calix-shaped macrocycles, carrying an all cis 1,3,7-cyclodecatriene core and supporting a 2,2-biindolylidene moiety. The syntheses of these high value-added compounds is operationally simple and can be performed at room temperature under mild, neutral and environmentally friendly conditions.
Fil: Silveira, Claudio C.. Universidade Federal de Santa Maria; Brasil
Fil: Mendes, Samuel R.. Universidade Federal de Santa Catarina; Brasil
Fil: Villetti, Marcos A.. Universidade Federal de Santa Maria; Brasil
Fil: Back, Davi F.. Universidade Federal de Santa Maria; Brasil
Fil: Kaufman, Teodoro Saul. 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 Indoles and benzaldehyde derivatives undergo an efficient one-pot smooth condensation and a further atmospheric-pressure aerobic dehydrogenation with CeCl3 in i-PrOH, to afford the corresponding oxidized bis(indol-3-yl)methanes. Use of 2,2-bisindole as the heterocyclic precursor provides cyclic tetra(indolyl)dimethane derivatives, which further undergo partial oxidation to the related calix-shaped macrocycles, carrying an all cis 1,3,7-cyclodecatriene core and supporting a 2,2-biindolylidene moiety. The syntheses of these high value-added compounds is operationally simple and can be performed at room temperature under mild, neutral and environmentally friendly conditions.
publishDate 2012
dc.date.none.fl_str_mv 2012-08
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/11336/105098
Silveira, Claudio C.; Mendes, Samuel R.; Villetti, Marcos A.; Back, Davi F.; Kaufman, Teodoro Saul; CeIII-promoted oxidation: Efficient aerobic one-pot eco-friendly synthesis of oxidized bis(indol-3-yl)methanes and cyclic tetra(indolyl)dimethanes; Royal Society of Chemistry; Green Chemistry (print); 14; 10; 8-2012; 2912-2921
1463-9262
CONICET Digital
CONICET
url http://hdl.handle.net/11336/105098
identifier_str_mv Silveira, Claudio C.; Mendes, Samuel R.; Villetti, Marcos A.; Back, Davi F.; Kaufman, Teodoro Saul; CeIII-promoted oxidation: Efficient aerobic one-pot eco-friendly synthesis of oxidized bis(indol-3-yl)methanes and cyclic tetra(indolyl)dimethanes; Royal Society of Chemistry; Green Chemistry (print); 14; 10; 8-2012; 2912-2921
1463-9262
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://pubs.rsc.org/en/content/articlelanding/2012/GC/c2gc36131k#!divAbstract
info:eu-repo/semantics/altIdentifier/doi/10.1039/c2gc36131k
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
dc.publisher.none.fl_str_mv Royal Society of Chemistry
publisher.none.fl_str_mv Royal Society of Chemistry
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_ 1842980376481366016
score 12.993085

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