Allylic azides as potential building blocks for the synthesis of nitrogenated compounds

Detalhes bibliográficos
Autor(a) principal: Sá,Marcus M.
Data de Publicação: 2003
Tipo de documento: Artigo
Idioma: eng
Título da fonte: Journal of the Brazilian Chemical Society (Online)
Texto Completo: http://old.scielo.br/scielo.php?script=sci_arttext&pid=S0103-50532003000600018
Resumo: The synthetic potential of multifunctional allylic azides and imines in attempted intramolecular cyclizations to nitrogen-containing heterocycles was investigated. Tandem Staudinger/aza-Wittig reaction of (E)-3-aryl-2-(azidomethyl)propenoates with triphenylphosphine and aldehydes yielded N-allylic imines in good yield. The (E)-stereochemistry of C=C and C=N bonds was assigned based on NOESY experiments. AlCl3 mediated formation of 3-carbomethoxyquinoline from methyl (E)-2-(azidomethyl)-3-phenylpropenoate is also described.
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spelling Allylic azides as potential building blocks for the synthesis of nitrogenated compoundsallylic azides3-carbomethoxyquinolineN-allylic iminesStaudinger/aza-Wittig reactionBaylis-Hillman reactionThe synthetic potential of multifunctional allylic azides and imines in attempted intramolecular cyclizations to nitrogen-containing heterocycles was investigated. Tandem Staudinger/aza-Wittig reaction of (E)-3-aryl-2-(azidomethyl)propenoates with triphenylphosphine and aldehydes yielded N-allylic imines in good yield. The (E)-stereochemistry of C=C and C=N bonds was assigned based on NOESY experiments. AlCl3 mediated formation of 3-carbomethoxyquinoline from methyl (E)-2-(azidomethyl)-3-phenylpropenoate is also described.Sociedade Brasileira de Química2003-12-01info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersiontext/htmlhttp://old.scielo.br/scielo.php?script=sci_arttext&pid=S0103-50532003000600018Journal of the Brazilian Chemical Society v.14 n.6 2003reponame:Journal of the Brazilian Chemical Society (Online)instname:Sociedade Brasileira de Química (SBQ)instacron:SBQ10.1590/S0103-50532003000600018info:eu-repo/semantics/openAccessSá,Marcus M.eng2004-02-11T00:00:00Zoai:scielo:S0103-50532003000600018Revistahttp://jbcs.sbq.org.brONGhttps://old.scielo.br/oai/scielo-oai.php||office@jbcs.sbq.org.br1678-47900103-5053opendoar:2004-02-11T00:00Journal of the Brazilian Chemical Society (Online) - Sociedade Brasileira de Química (SBQ)false
dc.title.none.fl_str_mv Allylic azides as potential building blocks for the synthesis of nitrogenated compounds
title Allylic azides as potential building blocks for the synthesis of nitrogenated compounds
spellingShingle Allylic azides as potential building blocks for the synthesis of nitrogenated compounds
Sá,Marcus M.
allylic azides
3-carbomethoxyquinoline
N-allylic imines
Staudinger/aza-Wittig reaction
Baylis-Hillman reaction
title_short Allylic azides as potential building blocks for the synthesis of nitrogenated compounds
title_full Allylic azides as potential building blocks for the synthesis of nitrogenated compounds
title_fullStr Allylic azides as potential building blocks for the synthesis of nitrogenated compounds
title_full_unstemmed Allylic azides as potential building blocks for the synthesis of nitrogenated compounds
title_sort Allylic azides as potential building blocks for the synthesis of nitrogenated compounds
author Sá,Marcus M.
author_facet Sá,Marcus M.
author_role author
dc.contributor.author.fl_str_mv Sá,Marcus M.
dc.subject.por.fl_str_mv allylic azides
3-carbomethoxyquinoline
N-allylic imines
Staudinger/aza-Wittig reaction
Baylis-Hillman reaction
topic allylic azides
3-carbomethoxyquinoline
N-allylic imines
Staudinger/aza-Wittig reaction
Baylis-Hillman reaction
description The synthetic potential of multifunctional allylic azides and imines in attempted intramolecular cyclizations to nitrogen-containing heterocycles was investigated. Tandem Staudinger/aza-Wittig reaction of (E)-3-aryl-2-(azidomethyl)propenoates with triphenylphosphine and aldehydes yielded N-allylic imines in good yield. The (E)-stereochemistry of C=C and C=N bonds was assigned based on NOESY experiments. AlCl3 mediated formation of 3-carbomethoxyquinoline from methyl (E)-2-(azidomethyl)-3-phenylpropenoate is also described.
publishDate 2003
dc.date.none.fl_str_mv 2003-12-01
dc.type.driver.fl_str_mv info:eu-repo/semantics/article
dc.type.status.fl_str_mv info:eu-repo/semantics/publishedVersion
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status_str publishedVersion
dc.identifier.uri.fl_str_mv http://old.scielo.br/scielo.php?script=sci_arttext&pid=S0103-50532003000600018
url http://old.scielo.br/scielo.php?script=sci_arttext&pid=S0103-50532003000600018
dc.language.iso.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv 10.1590/S0103-50532003000600018
dc.rights.driver.fl_str_mv info:eu-repo/semantics/openAccess
eu_rights_str_mv openAccess
dc.format.none.fl_str_mv text/html
dc.publisher.none.fl_str_mv Sociedade Brasileira de Química
publisher.none.fl_str_mv Sociedade Brasileira de Química
dc.source.none.fl_str_mv Journal of the Brazilian Chemical Society v.14 n.6 2003
reponame:Journal of the Brazilian Chemical Society (Online)
instname:Sociedade Brasileira de Química (SBQ)
instacron:SBQ
instname_str Sociedade Brasileira de Química (SBQ)
instacron_str SBQ
institution SBQ
reponame_str Journal of the Brazilian Chemical Society (Online)
collection Journal of the Brazilian Chemical Society (Online)
repository.name.fl_str_mv Journal of the Brazilian Chemical Society (Online) - Sociedade Brasileira de Química (SBQ)
repository.mail.fl_str_mv ||office@jbcs.sbq.org.br
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