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dc.contributor.author | Gómez Gil, Sara | |
dc.contributor.author | Solas Luera, Marta | |
dc.contributor.author | Suárez Pantiga, Samuel | |
dc.contributor.author | Sanz Díez, Roberto | |
dc.date.accessioned | 2024-07-01T06:53:37Z | |
dc.date.available | 2024-07-01T06:53:37Z | |
dc.date.issued | 2023-12-12 | |
dc.identifier.issn | 0022-3263 | |
dc.identifier.uri | http://hdl.handle.net/10259/9317 | |
dc.description.abstract | A 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.sponsorship | We 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.mimetype | application/pdf | |
dc.language.iso | eng | es |
dc.publisher | ACS Publications | en |
dc.relation.ispartof | The Journal of Organic Chemistry. 2023, V. 89, n. 1, p. 505-520 | en |
dc.rights | Atribución 4.0 Internacional | * |
dc.rights.uri | http://creativecommons.org/licenses/by/4.0/ | * |
dc.subject.other | Química orgánica | es |
dc.subject.other | Chemistry, Organic | en |
dc.title | Brønsted Acid-Catalyzed Synthesis of 4-Functionalized Tetrahydrocarbazol-1-ones from 1,4-Dicarbonylindole Derivatives | en |
dc.type | info:eu-repo/semantics/article | es |
dc.rights.accessRights | info:eu-repo/semantics/openAccess | es |
dc.relation.publisherversion | https://doi.org/10.1021/acs.joc.3c02248 | es |
dc.identifier.doi | 10.1021/acs.joc.3c02248 | |
dc.identifier.essn | 1520-6904 | |
dc.journal.title | The Journal of Organic Chemistry | en |
dc.volume.number | 89 | es |
dc.issue.number | 1 | es |
dc.page.initial | 505 | es |
dc.page.final | 520 | es |
dc.type.hasVersion | info:eu-repo/semantics/publishedVersion | es |