Nucleophile- or light-induced synthesis of 3-substituted phthalides from 2-formylarylketones

Autores
Gerbino, Darío César; Augner, Daniel; Slavov, Nikolay; Schmalz, Hans Günther
Año de publicación
2012
Idioma
inglés
Tipo de recurso
artículo
Estado
versión publicada
Descripción
The surprisingly facile conversion (isomerization) of 2-formyl-arylketones into 3-substituted phthalides, as observed for the marine natural product pestalone and its per-O-methylated derivative, was investigated using a series of simple 2-acylbenzaldehydes as substrates. The transformation generally proceeds smoothly in DMSO, either in a Cannizarro-Tishchenko-type reaction under nucleophile catalysis (NaCN) or under photochemical conditions (DMSO, 350 nm). © 2012 American Chemical Society.
Fil: Gerbino, Darío César. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina. University of Cologne; Alemania
Fil: Augner, Daniel. University of Cologne; Alemania
Fil: Slavov, Nikolay. University of Cologne; Alemania
Fil: Schmalz, Hans Günther. University of Cologne; Alemania
Materia
2-Formylarylketones
Phthalides
Cannizarro-Tishchenko-type reaction
Pestalone
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:11336/63935
Acceder
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oai_identifier_str oai:ri.conicet.gov.ar:11336/63935
network_acronym_str CONICETDig
repository_id_str 3498
network_name_str CONICET Digital (CONICET)
spelling Nucleophile- or light-induced synthesis of 3-substituted phthalides from 2-formylarylketonesGerbino, Darío CésarAugner, DanielSlavov, NikolaySchmalz, Hans Günther2-FormylarylketonesPhthalidesCannizarro-Tishchenko-type reactionPestalonehttps://purl.org/becyt/ford/1.4https://purl.org/becyt/ford/1The surprisingly facile conversion (isomerization) of 2-formyl-arylketones into 3-substituted phthalides, as observed for the marine natural product pestalone and its per-O-methylated derivative, was investigated using a series of simple 2-acylbenzaldehydes as substrates. The transformation generally proceeds smoothly in DMSO, either in a Cannizarro-Tishchenko-type reaction under nucleophile catalysis (NaCN) or under photochemical conditions (DMSO, 350 nm). © 2012 American Chemical Society.Fil: Gerbino, Darío César. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina. University of Cologne; AlemaniaFil: Augner, Daniel. University of Cologne; AlemaniaFil: Slavov, Nikolay. University of Cologne; AlemaniaFil: Schmalz, Hans Günther. University of Cologne; AlemaniaAmerican Chemical Society2012-05info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionhttp://purl.org/coar/resource_type/c_6501info:ar-repo/semantics/articuloapplication/pdfapplication/pdfhttp://hdl.handle.net/11336/63935Gerbino, Darío César; Augner, Daniel; Slavov, Nikolay; Schmalz, Hans Günther; Nucleophile- or light-induced synthesis of 3-substituted phthalides from 2-formylarylketones; American Chemical Society; Organic Letters; 14; 9; 5-2012; 2338-23411523-7060CONICET DigitalCONICETenginfo:eu-repo/semantics/altIdentifier/doi/10.1021/ol300757minfo:eu-repo/semantics/altIdentifier/url/https://pubs.acs.org/doi/10.1021/ol300757minfo:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by-nc-sa/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2026-01-14T12:39:49Zoai:ri.conicet.gov.ar:11336/63935instacron: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 12:39:49.735CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse
dc.title.none.fl_str_mv Nucleophile- or light-induced synthesis of 3-substituted phthalides from 2-formylarylketones
title Nucleophile- or light-induced synthesis of 3-substituted phthalides from 2-formylarylketones
spellingShingle Nucleophile- or light-induced synthesis of 3-substituted phthalides from 2-formylarylketones
Gerbino, Darío César
2-Formylarylketones
Phthalides
Cannizarro-Tishchenko-type reaction
Pestalone
title_short Nucleophile- or light-induced synthesis of 3-substituted phthalides from 2-formylarylketones
title_full Nucleophile- or light-induced synthesis of 3-substituted phthalides from 2-formylarylketones
title_fullStr Nucleophile- or light-induced synthesis of 3-substituted phthalides from 2-formylarylketones
title_full_unstemmed Nucleophile- or light-induced synthesis of 3-substituted phthalides from 2-formylarylketones
title_sort Nucleophile- or light-induced synthesis of 3-substituted phthalides from 2-formylarylketones
dc.creator.none.fl_str_mv Gerbino, Darío César
Augner, Daniel
Slavov, Nikolay
Schmalz, Hans Günther
author Gerbino, Darío César
author_facet Gerbino, Darío César
Augner, Daniel
Slavov, Nikolay
Schmalz, Hans Günther
author_role author
author2 Augner, Daniel
Slavov, Nikolay
Schmalz, Hans Günther
author2_role author
author
author
dc.subject.none.fl_str_mv 2-Formylarylketones
Phthalides
Cannizarro-Tishchenko-type reaction
Pestalone
topic 2-Formylarylketones
Phthalides
Cannizarro-Tishchenko-type reaction
Pestalone
purl_subject.fl_str_mv https://purl.org/becyt/ford/1.4
https://purl.org/becyt/ford/1
dc.description.none.fl_txt_mv The surprisingly facile conversion (isomerization) of 2-formyl-arylketones into 3-substituted phthalides, as observed for the marine natural product pestalone and its per-O-methylated derivative, was investigated using a series of simple 2-acylbenzaldehydes as substrates. The transformation generally proceeds smoothly in DMSO, either in a Cannizarro-Tishchenko-type reaction under nucleophile catalysis (NaCN) or under photochemical conditions (DMSO, 350 nm). © 2012 American Chemical Society.
Fil: Gerbino, Darío César. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina. University of Cologne; Alemania
Fil: Augner, Daniel. University of Cologne; Alemania
Fil: Slavov, Nikolay. University of Cologne; Alemania
Fil: Schmalz, Hans Günther. University of Cologne; Alemania
description The surprisingly facile conversion (isomerization) of 2-formyl-arylketones into 3-substituted phthalides, as observed for the marine natural product pestalone and its per-O-methylated derivative, was investigated using a series of simple 2-acylbenzaldehydes as substrates. The transformation generally proceeds smoothly in DMSO, either in a Cannizarro-Tishchenko-type reaction under nucleophile catalysis (NaCN) or under photochemical conditions (DMSO, 350 nm). © 2012 American Chemical Society.
publishDate 2012
dc.date.none.fl_str_mv 2012-05
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/11336/63935
Gerbino, Darío César; Augner, Daniel; Slavov, Nikolay; Schmalz, Hans Günther; Nucleophile- or light-induced synthesis of 3-substituted phthalides from 2-formylarylketones; American Chemical Society; Organic Letters; 14; 9; 5-2012; 2338-2341
1523-7060
CONICET Digital
CONICET
url http://hdl.handle.net/11336/63935
identifier_str_mv Gerbino, Darío César; Augner, Daniel; Slavov, Nikolay; Schmalz, Hans Günther; Nucleophile- or light-induced synthesis of 3-substituted phthalides from 2-formylarylketones; American Chemical Society; Organic Letters; 14; 9; 5-2012; 2338-2341
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/ol300757m
info:eu-repo/semantics/altIdentifier/url/https://pubs.acs.org/doi/10.1021/ol300757m
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
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score 12.603104

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