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dc.contributor.authorGómez Gil, Sara 
dc.contributor.authorSolas Luera, Marta 
dc.contributor.authorSuárez Pantiga, Samuel 
dc.contributor.authorSanz Díez, Roberto 
dc.date.accessioned2024-07-01T06:53:37Z
dc.date.available2024-07-01T06:53:37Z
dc.date.issued2023-12-12
dc.identifier.issn0022-3263
dc.identifier.urihttp://hdl.handle.net/10259/9317
dc.description.abstractA p-toluenesulfonic acid-catalyzed cascade reaction is reported for the synthesis of 4-functionalized tetrahydrocarbazolones via the reaction of 4-(indol-2-yl)-4-oxobutanal derivatives with a variety of nucleophiles in acetonitrile or hexafluoroisopropanol. After the initial intramolecular Friedel–Crafts hydroxyalkylation, the 3-indolylmethanol intermediate is subsequently activated and reacted with the external nucleophile. The reaction conditions are crucial to avoid alternative reaction pathways, allowing direct substitution reaction with thiols, (hetero)arenes, alkenes, or sulfinates. The procedure features high overall yields to access a diverse family of compounds bearing the tetrahydrocarbazole core.en
dc.description.sponsorshipWe gratefully acknowledge Ministerio de Ciencia e Innovación (PID2020-115789GB-C21/AEI/10.13039/501100011033), and Junta de Castilla y León and FEDER (BU049P20) for financial support. S.G.-G. thanks Ministerio de Educación for a FPU predoctoral contract. S.S.-P. thanks a Ramón y Cajal (RYC2021-031533-I) contract funded by MCIN/AEI/10.13039/501100011033 and European Union “NextGenerationEU”/PRTR.en
dc.format.mimetypeapplication/pdf
dc.language.isoenges
dc.publisherACS Publicationsen
dc.relation.ispartofThe Journal of Organic Chemistry. 2023, V. 89, n. 1, p. 505-520en
dc.rightsAtribución 4.0 Internacional*
dc.rights.urihttp://creativecommons.org/licenses/by/4.0/*
dc.subject.otherQuímica orgánicaes
dc.subject.otherChemistry, Organicen
dc.titleBrønsted Acid-Catalyzed Synthesis of 4-Functionalized Tetrahydrocarbazol-1-ones from 1,4-Dicarbonylindole Derivativesen
dc.typeinfo:eu-repo/semantics/articlees
dc.rights.accessRightsinfo:eu-repo/semantics/openAccesses
dc.relation.publisherversionhttps://doi.org/10.1021/acs.joc.3c02248es
dc.identifier.doi10.1021/acs.joc.3c02248
dc.identifier.essn1520-6904
dc.journal.titleThe Journal of Organic Chemistryen
dc.volume.number89es
dc.issue.number1es
dc.page.initial505es
dc.page.final520es
dc.type.hasVersioninfo:eu-repo/semantics/publishedVersiones


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