Efficient Buchwald–Hartwig and nitrene-mediated five-membered ring closure approaches to the total synthesis of quindoline. Unexpected direct conversion of a nitro group into a phosphazene

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dc.citation.titleRSC Advances
dc.citation.volume13
dc.contributor.orcidhttps://orcid.org/0000-0001-5780-6433
dc.contributor.orcidhttps://orcid.org/0000-0003-4236-7380
dc.contributor.orcidhttps://orcid.org/0000-0003-3173-2178
dc.contributor.orcidhttps://orcid.org/0000-0002-9791-4831
dc.contributor.orcidhttps://orcid.org/0000-0003-2647-475X
dc.creatorThobokholt, Elida N.
dc.creatorSimonetti, Sebastián Osvaldo
dc.creatorKaufman, Teodoro Saúl
dc.creatorLarghi, Enrique Leandro
dc.creatorBracca, Andrea Beatriz Juana
dc.date.accessioned2024-07-05T13:19:08Z
dc.date.available2024-07-05T13:19:08Z
dc.date.issued2023-05-05
dc.description.abstractTwo total syntheses of quindoline, which take place through the intermediacy of 3-nitroquinoline derivatives, are reported. The general synthetic sequence involves construction of the latter by mechanochemical condensation of benzaldehydes with 2-amino-nitrostyrene, followed either by reduction of the nitro group of the heterocycle and Buchwald–Hartwig cyclization or by a nitrenemediated cyclization under solventless conditions. Use of PPh3 to generate the nitrene resulted in the unprecedented formation of a phosphazene in place of quindoline. This unexpected transformation was explained by means of DFT computations.
dc.description.filFil: Thobokholt, Elida N. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas. Instituto de Química Rosario (IQUIR,-CONICET); Argentina.
dc.description.filFil: Simonetti, Sebastián Osvaldo. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas. Instituto de Química Rosario (IQUIR,-CONICET); Argentina.
dc.description.filFil: Kaufman, Teodoro Saúl. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas. Instituto de Química Rosario (IQUIR,-CONICET); Argentina.
dc.description.filFil: Larghi, Enrique Leandro. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas. Instituto de Química Rosario (IQUIR,-CONICET); Argentina.
dc.description.filFil: Bracca, Andrea Beatriz Juana. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas. Instituto de Química Rosario (IQUIR,-CONICET); Argentina.
dc.description.sponsorshipConsejo Nacional de Investigaciones Científicas y Técnicas (CONICET): PUE IQUIR-2016
dc.description.sponsorshipAgencia Nacional de Promoción Científica y Tecnológica : PICT 2018-1933, PICT 2019-3969
dc.format.extent13715–13724
dc.identifier.issn2046-2069
dc.identifier.urihttps://hdl.handle.net/2133/27436
dc.language.isoen
dc.publisherRoyal Society of Chemistry
dc.relation.publisherversionhttps://doi.org/10.1039/d3ra02468g
dc.relation.publisherversionhttps://pubs.rsc.org/en/content/articlelanding/2023/ra/d3ra02468g
dc.rightsopenAccess
dc.rights.holderThobokholt, Elida N.
dc.rights.holderSimonetti, Sebastián Osvaldo
dc.rights.holderKaufman, Teodoro Saúl
dc.rights.holderLarghi, Enrique Leandro
dc.rights.holderBracca, Andrea Beatriz Juana
dc.rights.holderUniversidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas
dc.rights.textAttribution-NonCommercial 4.0 Internationalen
dc.rights.urihttp://creativecommons.org/licenses/by-nc/4.0/
dc.subjectBenzaldehydes
dc.subjectCyclization
dc.subjectQuindoline
dc.subjectBuchwald–hartwig amination
dc.titleEfficient Buchwald–Hartwig and nitrene-mediated five-membered ring closure approaches to the total synthesis of quindoline. Unexpected direct conversion of a nitro group into a phosphazene
dc.typearticulo
dc.type.collectionarticulo
dc.type.versionpublishedVersion

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