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Intramolecular addition of acyldiazenecarboxylates onto double bonds in the synthesis of heterocycles

2002-01-23Journal article Restricted access
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dc.contributor.authorPrata, José V.
dc.contributor.authorClemente, Dina-Telma S.
dc.contributor.authorPrabhakar, Sundaresan
dc.contributor.authorLobo, Ana M.
dc.contributor.authorMourato, Isabel
dc.contributor.authorBranco, Paula Sério
dc.date.accessioned2020-06-09T18:15:06Z
dc.date.available2020-06-09T18:15:06Z
dc.date.issued2002-01-23
dc.description.abstractAppropriate aryl-substituted unsymmetrical azodicarbonyl compounds, generated from bishydrazides by oxidation, undergo intramolecular cyclisations to furnish a variety of useful heterocycles such as N-substituted oxindoles, carbostyrils, benzazepinones, benzazocinones, benzimidazolones, benzoxazinones and pyrazolones in varying degrees of efficiency. Methods are described to remove the N-acyl groups from the heteroaromatic compounds. Under mildly acidic conditions where equal opportunities are available for an ipso or a normal cyclisation it is the former process that occurs preferentially. Evidence is presented in favour of a C-to-C migration in the ipso product for the formation of a methoxy-substituted carbostyril derivative. One of the spiro substances is shown to participate in dienone–phenol rearrangement to provide the corresponding quinolone–phenol in high yield.pt_PT
dc.description.versioninfo:eu-repo/semantics/publishedVersionpt_PT
dc.identifier.citationPRATA, José V.; [et al] – Intramolecular addition of acyldiazenecarboxylates onto double bonds in the synthesis of heterocycles. Journal of the Chemical Society, Perkin Transactions 1. ISSN 1470-4358. N.º 4 (2002), pp. 513-528pt_PT
dc.identifier.doi10.1039/B110414Dpt_PT
dc.identifier.issn1470-4358
dc.identifier.urihttp://hdl.handle.net/10400.21/11815
dc.language.isoengpt_PT
dc.peerreviewedyespt_PT
dc.publisherRoyal Society of Chemistrypt_PT
dc.relation.publisherversionhttps://pubs.rsc.org/en/content/articlepdf/2002/p1/b110414dpt_PT
dc.subjectIntramolecularpt_PT
dc.subjectAcyldiazenecarboxylatespt_PT
dc.subjectSynthesispt_PT
dc.subjectHeterocyclespt_PT
dc.titleIntramolecular addition of acyldiazenecarboxylates onto double bonds in the synthesis of heterocyclespt_PT
dc.typejournal article
dspace.entity.typePublication
oaire.citation.endPage528pt_PT
oaire.citation.issue4pt_PT
oaire.citation.startPage513pt_PT
oaire.citation.titleJournal of the Chemical Society, Perkin Transactions 1pt_PT
person.familyNamePrata
person.familyNameLobo
person.familyNameBranco
person.givenNameJosé Virgílio
person.givenNameAna
person.givenNamePaula
person.identifier191765
person.identifier.ciencia-idC11A-9130-8981
person.identifier.ciencia-id3D12-0B91-9DD0
person.identifier.orcid0000-0002-9068-2847
person.identifier.orcid0000-0002-7677-8316
person.identifier.orcid0000-0002-7312-8596
person.identifier.ridB-7214-2008
person.identifier.ridC-9603-2013
person.identifier.ridI-6567-2012
person.identifier.scopus-author-id9276778400
person.identifier.scopus-author-id7102068595
person.identifier.scopus-author-id7005118613
rcaap.rightsclosedAccesspt_PT
rcaap.typearticlept_PT
relation.isAuthorOfPublication15e229f3-a619-4931-87eb-799091dc1601
relation.isAuthorOfPublication9b3bdcea-2025-4a1d-9d99-7b1aa16fb2ee
relation.isAuthorOfPublication4061a146-1828-4f5e-9e90-04c9698b987b
relation.isAuthorOfPublication.latestForDiscovery9b3bdcea-2025-4a1d-9d99-7b1aa16fb2ee

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