Efficient total synthesis of neocryptolepine and synthetic access to 6-methylquinindoline from a common intermediate

dc.citation.titleRSC Advanceses
dc.citation.volume7es
dc.creatorKaufman, Teodoro Saúl
dc.creatorLarghi, Enrique Leandro
dc.creatorBracca, Andrea Beatriz Juana
dc.creatorHeredia, Daniel Alejandro
dc.creatorMendez, María Virginia
dc.date.accessioned2017-11-15T00:12:00Z
dc.date.available2017-11-15T00:12:00Z
dc.date.issued2017-05-23
dc.descriptionA convenient approach toward the indoloquinolines neocryptolepine and 6-methylquinindoline from a common intermediate, is reported. Both sequences, designed for maximum use of accessible reagents and robust conditions, are straightforward and efficient. They involved the amidation of 2- aminobenzaldehyde (prepared by iron-mediated reduction of 2-nitrobenzaldehyde) with 2- nitrophenylacetic acid, followed by a K2CO3-assisted cyclization to form a 3-(2-nitrophenyl)quinolin-2- one as the common precursor. Me2CO3-mediated N-methylation of the lactam, reduction of the nitro moiety and final cyclization resulted in 55% overall yield of neocryptolepine, whereas cyclocondensation and N-methylation afforded 79% overall yield of 6-methyl quinindoline. Thus, the sequences toward the targets entailed two POCl3-promoted C–N bond forming reactions, two Fe-mediated nitro group reductions and two base-promoted transformations.es
dc.description.filFil: Kaufman, Teodoro Saúl. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas. Instituto de Química Rosario. CONICET; Argentinaes
dc.description.filFil: Larghi, Enrique Leandro. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas. Instituto de Química Rosario. CONICET; Argentinaes
dc.description.filFil: Bracca, Andrea Beatriz Juana. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas. Instituto de Química Rosario. CONICET; Argentinaes
dc.description.filFil: Heredia, Daniel Alejandro. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas. Instituto de Química Rosario. CONICET; Argentina.es
dc.description.filFil: Mendez, María Virginia. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas. Instituto de Química Rosario. CONICET; Argentina.es
dc.description.sponsorshipUniversidad Nacional de Rosario. Secretaría de Ciencia y Tecnología.es
dc.description.sponsorshipConsejo Nacional de Investigaciones Científicas y Técnicases
dc.description.sponsorshipAgencia Nacional de Promoción Científica y Tecnológicaes
dc.formatapplication/pdf
dc.format.extent28298–28307es
dc.identifier.issn2046-2069es
dc.identifier.urihttp://hdl.handle.net/2133/9279
dc.language.isoenges
dc.publisherThe Royal Society of Chemistryes
dc.relation.publisherversionhttp://pubs.rsc.org/en/content/articlelanding/2017/ra/c7ra05349e#!divAbstractes
dc.relation.publisherversionDOI: 10.1039/c7ra05349ees
dc.rightsopenAccesses
dc.rights.holderThe Royal Society of Chemistryes
dc.rights.urihttp://creativecommons.org/licenses/by-nc-sa/2.5/ar/*
dc.subjectTotal synthesises
dc.subjectNatural productes
dc.subjectHeterocycleses
dc.subjectNeocryptolepinees
dc.subjectQuinindolinees
dc.subjectIndoloquinolineses
dc.titleEfficient total synthesis of neocryptolepine and synthetic access to 6-methylquinindoline from a common intermediatees
dc.typearticle
dc.typeartículo
dc.typepublishedVersion
dc.type.collectionarticulo
dc.type.versionpublishedVersiones

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