Synthetic approaches to multifunctional indenes

The synthesis of multifunctional indenes with at least two different functional groups has not yet been extensively explored. Among the plausible synthetic routes to 3,5-disubstituted indenes bearing two different functional groups, such as the [3-(aminoethyl)inden-5-yl)]amines, a reasonable pathway...

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Autores: Mesquida Estévez, Ma. Neus, López Pérez, Sara, Dinarès Milà, M. Immaculada, Alcalde Pais, Ma. Ermitas (María de las Ermitas)
Tipo de recurso: artículo
Estado:Versión publicada
Fecha de publicación:2011
País:España
Institución:Universidad de Barcelona
Repositorio:Dipòsit Digital de la UB
OAI Identifier:oai:diposit.ub.edu:2445/120566
Acceso en línea:https://hdl.handle.net/2445/120566
Access Level:acceso abierto
Palabra clave:Síntesi orgànica
Compostos organometàl·lics
Compostos policíclics
Amides
Organic synthesis
Organometallic compounds
Polycyclic compounds
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spelling Synthetic approaches to multifunctional indenesMesquida Estévez, Ma. NeusLópez Pérez, SaraDinarès Milà, M. ImmaculadaAlcalde Pais, Ma. Ermitas (María de las Ermitas)Síntesi orgànicaCompostos organometàl·licsCompostos policíclicsAmidesOrganic synthesisOrganometallic compoundsPolycyclic compoundsAmidesThe synthesis of multifunctional indenes with at least two different functional groups has not yet been extensively explored. Among the plausible synthetic routes to 3,5-disubstituted indenes bearing two different functional groups, such as the [3-(aminoethyl)inden-5-yl)]amines, a reasonable pathway involves the (5-nitro-3-indenyl)acetamides as key intermediates. Although several multistep synthetic approaches can be applied to obtain these advanced intermediates, we describe herein their preparation by an aldol-type reaction between 5-nitroindan-1-ones and the lithium salt of N,N-disubstituted acetamides, followed immediately by dehydration with acid. This classical condensation process, which is neither simple nor trivial despite its apparent directness, permits an efficient entry to a variety of indene-based molecular modules, which could be adapted to a range of functionalized indanones.Beilstein Institute2011info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionapplication/pdfhttps://hdl.handle.net/2445/120566Articles publicats en revistes (Farmacologia, Toxicologia i Química Terapèutica)reponame:Dipòsit Digital de la UBinstname:Universidad de BarcelonaInglésReproducció del document publicat a: https://doi.org/10.3762/bjoc.7.204Beilstein Journal of Organic Chemistry, 2011, vol. 7, p. 1739-1744https://doi.org/10.3762/bjoc.7.204cc-by (c) Mesquida Estévez, Ma. Neus et al., 2011http://creativecommons.org/licenses/by/3.0/esinfo:eu-repo/semantics/openAccessoai:diposit.ub.edu:2445/1205662026-05-27T06:46:51Z
dc.title.none.fl_str_mv Synthetic approaches to multifunctional indenes
title Synthetic approaches to multifunctional indenes
spellingShingle Synthetic approaches to multifunctional indenes
Mesquida Estévez, Ma. Neus
Síntesi orgànica
Compostos organometàl·lics
Compostos policíclics
Amides
Organic synthesis
Organometallic compounds
Polycyclic compounds
Amides
title_short Synthetic approaches to multifunctional indenes
title_full Synthetic approaches to multifunctional indenes
title_fullStr Synthetic approaches to multifunctional indenes
title_full_unstemmed Synthetic approaches to multifunctional indenes
title_sort Synthetic approaches to multifunctional indenes
dc.creator.none.fl_str_mv Mesquida Estévez, Ma. Neus
López Pérez, Sara
Dinarès Milà, M. Immaculada
Alcalde Pais, Ma. Ermitas (María de las Ermitas)
author Mesquida Estévez, Ma. Neus
author_facet Mesquida Estévez, Ma. Neus
López Pérez, Sara
Dinarès Milà, M. Immaculada
Alcalde Pais, Ma. Ermitas (María de las Ermitas)
author_role author
author2 López Pérez, Sara
Dinarès Milà, M. Immaculada
Alcalde Pais, Ma. Ermitas (María de las Ermitas)
author2_role author
author
author
dc.subject.none.fl_str_mv Síntesi orgànica
Compostos organometàl·lics
Compostos policíclics
Amides
Organic synthesis
Organometallic compounds
Polycyclic compounds
Amides
topic Síntesi orgànica
Compostos organometàl·lics
Compostos policíclics
Amides
Organic synthesis
Organometallic compounds
Polycyclic compounds
Amides
description The synthesis of multifunctional indenes with at least two different functional groups has not yet been extensively explored. Among the plausible synthetic routes to 3,5-disubstituted indenes bearing two different functional groups, such as the [3-(aminoethyl)inden-5-yl)]amines, a reasonable pathway involves the (5-nitro-3-indenyl)acetamides as key intermediates. Although several multistep synthetic approaches can be applied to obtain these advanced intermediates, we describe herein their preparation by an aldol-type reaction between 5-nitroindan-1-ones and the lithium salt of N,N-disubstituted acetamides, followed immediately by dehydration with acid. This classical condensation process, which is neither simple nor trivial despite its apparent directness, permits an efficient entry to a variety of indene-based molecular modules, which could be adapted to a range of functionalized indanones.
publishDate 2011
dc.date.none.fl_str_mv 2011
dc.type.none.fl_str_mv info:eu-repo/semantics/article
info:eu-repo/semantics/publishedVersion
format article
status_str publishedVersion
dc.identifier.none.fl_str_mv https://hdl.handle.net/2445/120566
url https://hdl.handle.net/2445/120566
dc.language.none.fl_str_mv Inglés
language_invalid_str_mv Inglés
dc.relation.none.fl_str_mv Reproducció del document publicat a: https://doi.org/10.3762/bjoc.7.204
Beilstein Journal of Organic Chemistry, 2011, vol. 7, p. 1739-1744
https://doi.org/10.3762/bjoc.7.204
dc.rights.none.fl_str_mv cc-by (c) Mesquida Estévez, Ma. Neus et al., 2011
http://creativecommons.org/licenses/by/3.0/es
info:eu-repo/semantics/openAccess
rights_invalid_str_mv cc-by (c) Mesquida Estévez, Ma. Neus et al., 2011
http://creativecommons.org/licenses/by/3.0/es
eu_rights_str_mv openAccess
dc.format.none.fl_str_mv application/pdf
dc.publisher.none.fl_str_mv Beilstein Institute
publisher.none.fl_str_mv Beilstein Institute
dc.source.none.fl_str_mv Articles publicats en revistes (Farmacologia, Toxicologia i Química Terapèutica)
reponame:Dipòsit Digital de la UB
instname:Universidad de Barcelona
instname_str Universidad de Barcelona
reponame_str Dipòsit Digital de la UB
collection Dipòsit Digital de la UB
repository.name.fl_str_mv
repository.mail.fl_str_mv
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score 15,301603

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