N-Capping of primary amines with 2-Acylbenzaldehydes to give isoindolinones

Autores
Augner, Daniel; Gerbino, Darío César; Slavov, Nikolay; Neudörfl, Jörg-Martin; Schmalz, Hans-Günther
Año de publicación
2011
Idioma
inglés
Tipo de recurso
artículo
Estado
versión publicada
Descripción
A unique reactivity pattern, first observed in the conversion of the marine natural product pestalone into pestalachloride A, was investigated. It was shown that 2-formyl-arylketones smoothly react with ammonia and primary amines, respectively, under mild conditions to afford 3-substituted isoindolinones in high yield. The reaction represents a new option for the derivatization (N-capping) of primary amines. As the substrates are readily accessible the methodology opens a short and modular access to pharmaceutically relevant substituted isoindolinones.
Fil: Augner, Daniel. Universitat zu Köln; Alemania
Fil: Gerbino, Darío César. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Bahía Blanca. Instituto de Química del Sur. Universidad Nacional del Sur. Departamento de Química. Instituto de Química del Sur; Argentina. Universitat zu Köln; Alemania
Fil: Slavov, Nikolay. Universitat zu Köln; Alemania
Fil: Neudörfl, Jörg-Martin. Universitat zu Köln; Alemania
Fil: Schmalz, Hans-Günther. Universitat zu Köln; Alemania
Materia
2-Acylbenzaldehydes
Isoindolinones
Pestalone
antibiotic activity
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:11336/95353
Acceder
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network_acronym_str CONICETDig
repository_id_str 3498
network_name_str CONICET Digital (CONICET)
spelling N-Capping of primary amines with 2-Acylbenzaldehydes to give isoindolinonesAugner, DanielGerbino, Darío CésarSlavov, NikolayNeudörfl, Jörg-MartinSchmalz, Hans-Günther2-AcylbenzaldehydesIsoindolinonesPestaloneantibiotic activityhttps://purl.org/becyt/ford/1.4https://purl.org/becyt/ford/1A unique reactivity pattern, first observed in the conversion of the marine natural product pestalone into pestalachloride A, was investigated. It was shown that 2-formyl-arylketones smoothly react with ammonia and primary amines, respectively, under mild conditions to afford 3-substituted isoindolinones in high yield. The reaction represents a new option for the derivatization (N-capping) of primary amines. As the substrates are readily accessible the methodology opens a short and modular access to pharmaceutically relevant substituted isoindolinones.Fil: Augner, Daniel. Universitat zu Köln; AlemaniaFil: Gerbino, Darío César. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Bahía Blanca. Instituto de Química del Sur. Universidad Nacional del Sur. Departamento de Química. Instituto de Química del Sur; Argentina. Universitat zu Köln; AlemaniaFil: Slavov, Nikolay. Universitat zu Köln; AlemaniaFil: Neudörfl, Jörg-Martin. Universitat zu Köln; AlemaniaFil: Schmalz, Hans-Günther. Universitat zu Köln; AlemaniaAmerican Chemical Society2011-10info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionhttp://purl.org/coar/resource_type/c_6501info:ar-repo/semantics/articuloapplication/pdfapplication/pdfhttp://hdl.handle.net/11336/95353Augner, Daniel; Gerbino, Darío César; Slavov, Nikolay; Neudörfl, Jörg-Martin; Schmalz, Hans-Günther; N-Capping of primary amines with 2-Acylbenzaldehydes to give isoindolinones; American Chemical Society; Organic Letters; 13; 19; 10-2011; 5374-53771523-7060CONICET DigitalCONICETenginfo:eu-repo/semantics/altIdentifier/doi/10.1021/ol202271kinfo:eu-repo/semantics/altIdentifier/url/https://pubs.acs.org/doi/10.1021/ol202271kinfo:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by-nc-sa/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2026-01-14T12:35:30Zoai:ri.conicet.gov.ar:11336/95353instacron: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:34982026-01-14 12:35:31.016CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse
dc.title.none.fl_str_mv N-Capping of primary amines with 2-Acylbenzaldehydes to give isoindolinones
title N-Capping of primary amines with 2-Acylbenzaldehydes to give isoindolinones
spellingShingle N-Capping of primary amines with 2-Acylbenzaldehydes to give isoindolinones
Augner, Daniel
2-Acylbenzaldehydes
Isoindolinones
Pestalone
antibiotic activity
title_short N-Capping of primary amines with 2-Acylbenzaldehydes to give isoindolinones
title_full N-Capping of primary amines with 2-Acylbenzaldehydes to give isoindolinones
title_fullStr N-Capping of primary amines with 2-Acylbenzaldehydes to give isoindolinones
title_full_unstemmed N-Capping of primary amines with 2-Acylbenzaldehydes to give isoindolinones
title_sort N-Capping of primary amines with 2-Acylbenzaldehydes to give isoindolinones
dc.creator.none.fl_str_mv Augner, Daniel
Gerbino, Darío César
Slavov, Nikolay
Neudörfl, Jörg-Martin
Schmalz, Hans-Günther
author Augner, Daniel
author_facet Augner, Daniel
Gerbino, Darío César
Slavov, Nikolay
Neudörfl, Jörg-Martin
Schmalz, Hans-Günther
author_role author
author2 Gerbino, Darío César
Slavov, Nikolay
Neudörfl, Jörg-Martin
Schmalz, Hans-Günther
author2_role author
author
author
author
dc.subject.none.fl_str_mv 2-Acylbenzaldehydes
Isoindolinones
Pestalone
antibiotic activity
topic 2-Acylbenzaldehydes
Isoindolinones
Pestalone
antibiotic activity
purl_subject.fl_str_mv https://purl.org/becyt/ford/1.4
https://purl.org/becyt/ford/1
dc.description.none.fl_txt_mv A unique reactivity pattern, first observed in the conversion of the marine natural product pestalone into pestalachloride A, was investigated. It was shown that 2-formyl-arylketones smoothly react with ammonia and primary amines, respectively, under mild conditions to afford 3-substituted isoindolinones in high yield. The reaction represents a new option for the derivatization (N-capping) of primary amines. As the substrates are readily accessible the methodology opens a short and modular access to pharmaceutically relevant substituted isoindolinones.
Fil: Augner, Daniel. Universitat zu Köln; Alemania
Fil: Gerbino, Darío César. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Bahía Blanca. Instituto de Química del Sur. Universidad Nacional del Sur. Departamento de Química. Instituto de Química del Sur; Argentina. Universitat zu Köln; Alemania
Fil: Slavov, Nikolay. Universitat zu Köln; Alemania
Fil: Neudörfl, Jörg-Martin. Universitat zu Köln; Alemania
Fil: Schmalz, Hans-Günther. Universitat zu Köln; Alemania
description A unique reactivity pattern, first observed in the conversion of the marine natural product pestalone into pestalachloride A, was investigated. It was shown that 2-formyl-arylketones smoothly react with ammonia and primary amines, respectively, under mild conditions to afford 3-substituted isoindolinones in high yield. The reaction represents a new option for the derivatization (N-capping) of primary amines. As the substrates are readily accessible the methodology opens a short and modular access to pharmaceutically relevant substituted isoindolinones.
publishDate 2011
dc.date.none.fl_str_mv 2011-10
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/11336/95353
Augner, Daniel; Gerbino, Darío César; Slavov, Nikolay; Neudörfl, Jörg-Martin; Schmalz, Hans-Günther; N-Capping of primary amines with 2-Acylbenzaldehydes to give isoindolinones; American Chemical Society; Organic Letters; 13; 19; 10-2011; 5374-5377
1523-7060
CONICET Digital
CONICET
url http://hdl.handle.net/11336/95353
identifier_str_mv Augner, Daniel; Gerbino, Darío César; Slavov, Nikolay; Neudörfl, Jörg-Martin; Schmalz, Hans-Günther; N-Capping of primary amines with 2-Acylbenzaldehydes to give isoindolinones; American Chemical Society; Organic Letters; 13; 19; 10-2011; 5374-5377
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/ol202271k
info:eu-repo/semantics/altIdentifier/url/https://pubs.acs.org/doi/10.1021/ol202271k
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_ 1854321922015232000
score 12.603104

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