1-Substituted β-carbolines by a Pictet-Spengler cyclization with thioortho esters and carbon-carbon bond formation via N-sulfonyl iminium ions generated from N,S-sulfonyl acetals

Autores
Silveira, Claudio; Felix, Luciana A.; Braga, Antonio L.; Kaufman, Teodoro Saul
Año de publicación
2005
Idioma
inglés
Tipo de recurso
artículo
Estado
versión publicada
Descripción
(Chemical Equation Presented) The reaction of N-tosyltryptamines with thioortho esters, leading to 1-thiosubstituted tetrahydro-β-carbolines under modified Pictet-Spengler conditions, is described. The 1-heterosubstituted β-carbolines furnished 1-substituted β-carbolines upon reaction with Grignard reagents and silyl derivatives under Lewis acid promotion.
Fil: Silveira, Claudio. Universidade Federal de Santa Maria; Brasil
Fil: Felix, Luciana A.. Universidade Federal de Santa Maria; Brasil
Fil: Braga, Antonio L.. 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
BETA-CARBIOLINES
PICTET SPENGLER CYCLIZATION
ORGANOCHALCOHEN CHEMISTRY
SYNTHESIS OF HETEROCYCLES
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:11336/135502
Acceder
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oai_identifier_str oai:ri.conicet.gov.ar:11336/135502
network_acronym_str CONICETDig
repository_id_str 3498
network_name_str CONICET Digital (CONICET)
spelling 1-Substituted β-carbolines by a Pictet-Spengler cyclization with thioortho esters and carbon-carbon bond formation via N-sulfonyl iminium ions generated from N,S-sulfonyl acetalsSilveira, ClaudioFelix, Luciana A.Braga, Antonio L.Kaufman, Teodoro SaulBETA-CARBIOLINESPICTET SPENGLER CYCLIZATIONORGANOCHALCOHEN CHEMISTRYSYNTHESIS OF HETEROCYCLEShttps://purl.org/becyt/ford/1.4https://purl.org/becyt/ford/1(Chemical Equation Presented) The reaction of N-tosyltryptamines with thioortho esters, leading to 1-thiosubstituted tetrahydro-β-carbolines under modified Pictet-Spengler conditions, is described. The 1-heterosubstituted β-carbolines furnished 1-substituted β-carbolines upon reaction with Grignard reagents and silyl derivatives under Lewis acid promotion.Fil: Silveira, Claudio. Universidade Federal de Santa Maria; BrasilFil: Felix, Luciana A.. Universidade Federal de Santa Maria; BrasilFil: Braga, Antonio L.. 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; ArgentinaAmerican Chemical Society2005-08info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionhttp://purl.org/coar/resource_type/c_6501info:ar-repo/semantics/articuloapplication/pdfapplication/pdfhttp://hdl.handle.net/11336/135502Silveira, Claudio; Felix, Luciana A.; Braga, Antonio L.; Kaufman, Teodoro Saul; 1-Substituted β-carbolines by a Pictet-Spengler cyclization with thioortho esters and carbon-carbon bond formation via N-sulfonyl iminium ions generated from N,S-sulfonyl acetals; American Chemical Society; Organic Letters; 7; 17; 8-2005; 3701-37041523-7060CONICET DigitalCONICETenginfo:eu-repo/semantics/altIdentifier/doi/10.1021/ol051342iinfo:eu-repo/semantics/altIdentifier/url/https://pubs.acs.org/doi/10.1021/ol051342iinfo:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by-nc-sa/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2025-11-26T08:50:20Zoai:ri.conicet.gov.ar:11336/135502instacron: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:34982025-11-26 08:50:21.012CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse
dc.title.none.fl_str_mv 1-Substituted β-carbolines by a Pictet-Spengler cyclization with thioortho esters and carbon-carbon bond formation via N-sulfonyl iminium ions generated from N,S-sulfonyl acetals
title 1-Substituted β-carbolines by a Pictet-Spengler cyclization with thioortho esters and carbon-carbon bond formation via N-sulfonyl iminium ions generated from N,S-sulfonyl acetals
spellingShingle 1-Substituted β-carbolines by a Pictet-Spengler cyclization with thioortho esters and carbon-carbon bond formation via N-sulfonyl iminium ions generated from N,S-sulfonyl acetals
Silveira, Claudio
BETA-CARBIOLINES
PICTET SPENGLER CYCLIZATION
ORGANOCHALCOHEN CHEMISTRY
SYNTHESIS OF HETEROCYCLES
title_short 1-Substituted β-carbolines by a Pictet-Spengler cyclization with thioortho esters and carbon-carbon bond formation via N-sulfonyl iminium ions generated from N,S-sulfonyl acetals
title_full 1-Substituted β-carbolines by a Pictet-Spengler cyclization with thioortho esters and carbon-carbon bond formation via N-sulfonyl iminium ions generated from N,S-sulfonyl acetals
title_fullStr 1-Substituted β-carbolines by a Pictet-Spengler cyclization with thioortho esters and carbon-carbon bond formation via N-sulfonyl iminium ions generated from N,S-sulfonyl acetals
title_full_unstemmed 1-Substituted β-carbolines by a Pictet-Spengler cyclization with thioortho esters and carbon-carbon bond formation via N-sulfonyl iminium ions generated from N,S-sulfonyl acetals
title_sort 1-Substituted β-carbolines by a Pictet-Spengler cyclization with thioortho esters and carbon-carbon bond formation via N-sulfonyl iminium ions generated from N,S-sulfonyl acetals
dc.creator.none.fl_str_mv Silveira, Claudio
Felix, Luciana A.
Braga, Antonio L.
Kaufman, Teodoro Saul
author Silveira, Claudio
author_facet Silveira, Claudio
Felix, Luciana A.
Braga, Antonio L.
Kaufman, Teodoro Saul
author_role author
author2 Felix, Luciana A.
Braga, Antonio L.
Kaufman, Teodoro Saul
author2_role author
author
author
dc.subject.none.fl_str_mv BETA-CARBIOLINES
PICTET SPENGLER CYCLIZATION
ORGANOCHALCOHEN CHEMISTRY
SYNTHESIS OF HETEROCYCLES
topic BETA-CARBIOLINES
PICTET SPENGLER CYCLIZATION
ORGANOCHALCOHEN CHEMISTRY
SYNTHESIS OF HETEROCYCLES
purl_subject.fl_str_mv https://purl.org/becyt/ford/1.4
https://purl.org/becyt/ford/1
dc.description.none.fl_txt_mv (Chemical Equation Presented) The reaction of N-tosyltryptamines with thioortho esters, leading to 1-thiosubstituted tetrahydro-β-carbolines under modified Pictet-Spengler conditions, is described. The 1-heterosubstituted β-carbolines furnished 1-substituted β-carbolines upon reaction with Grignard reagents and silyl derivatives under Lewis acid promotion.
Fil: Silveira, Claudio. Universidade Federal de Santa Maria; Brasil
Fil: Felix, Luciana A.. Universidade Federal de Santa Maria; Brasil
Fil: Braga, Antonio L.. 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 (Chemical Equation Presented) The reaction of N-tosyltryptamines with thioortho esters, leading to 1-thiosubstituted tetrahydro-β-carbolines under modified Pictet-Spengler conditions, is described. The 1-heterosubstituted β-carbolines furnished 1-substituted β-carbolines upon reaction with Grignard reagents and silyl derivatives under Lewis acid promotion.
publishDate 2005
dc.date.none.fl_str_mv 2005-08
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/11336/135502
Silveira, Claudio; Felix, Luciana A.; Braga, Antonio L.; Kaufman, Teodoro Saul; 1-Substituted β-carbolines by a Pictet-Spengler cyclization with thioortho esters and carbon-carbon bond formation via N-sulfonyl iminium ions generated from N,S-sulfonyl acetals; American Chemical Society; Organic Letters; 7; 17; 8-2005; 3701-3704
1523-7060
CONICET Digital
CONICET
url http://hdl.handle.net/11336/135502
identifier_str_mv Silveira, Claudio; Felix, Luciana A.; Braga, Antonio L.; Kaufman, Teodoro Saul; 1-Substituted β-carbolines by a Pictet-Spengler cyclization with thioortho esters and carbon-carbon bond formation via N-sulfonyl iminium ions generated from N,S-sulfonyl acetals; American Chemical Society; Organic Letters; 7; 17; 8-2005; 3701-3704
1523-7060
CONICET Digital
CONICET
dc.language.none.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv info:eu-repo/semantics/altIdentifier/doi/10.1021/ol051342i
info:eu-repo/semantics/altIdentifier/url/https://pubs.acs.org/doi/10.1021/ol051342i
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 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
_version_ 1849872791197712384
score 13.011256

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