2026-05-11T16:26:52Zhttps://riubu.ubu.es/oai/request

oai:riubu.ubu.es:10259/93172024-07-02T00:05:22Zcom_10259_3593com_10259_5086com_10259_2604col_10259_3594

Gómez Gil, Sara c17cf50a-843a-443e-92b1-6a5607b46351 600 Solas Luera, Marta 542 600 0000-0002-0052-7270 Suarez Pantiga, Samuel 544 600 0000-0002-4249-7807 Sanz Díez, Roberto 531 600 0000-0003-2830-0892 2024-07-01T06:53:37Z 2024-07-01T06:53:37Z 2023-12-12 0022-3263 http://hdl.handle.net/10259/9317 10.1021/acs.joc.3c02248 1520-6904 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. 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. application/pdf eng ACS Publications The Journal of Organic Chemistry. 2023, V. 89, n. 1, p. 505-520 https://doi.org/10.1021/acs.joc.3c02248 Atribución 4.0 Internacional http://creativecommons.org/licenses/by/4.0/ info:eu-repo/semantics/openAccess Química orgánica Chemistry, Organic Brønsted Acid-Catalyzed Synthesis of 4-Functionalized Tetrahydrocarbazol-1-ones from 1,4-Dicarbonylindole Derivatives info:eu-repo/semantics/article info:eu-repo/semantics/publishedVersion The Journal of Organic Chemistry 89 1 505 520 THUMBNAIL Gomez-joc_2023.pdf.jpg Gomez-joc_2023.pdf.jpg IM Thumbnail image/jpeg 5320 https://riubu.ubu.es/bitstream/10259/9317/4/Gomez-joc_2023.pdf.jpg 884e06fa03a23e17f7c4703cf9deb290 MD5 4 LICENSE license.txt license.txt text/plain; charset=utf-8 999 https://riubu.ubu.es/bitstream/10259/9317/3/license.txt b295bcbce42e2caabeb0c623d3860c06 MD5 3 CC-LICENSE license_rdf license_rdf application/rdf+xml; charset=utf-8 908 https://riubu.ubu.es/bitstream/10259/9317/2/license_rdf 0175ea4a2d4caec4bbcc37e300941108 MD5 2 ORIGINAL Gomez-joc_2023.pdf Gomez-joc_2023.pdf application/pdf 2657196 https://riubu.ubu.es/bitstream/10259/9317/1/Gomez-joc_2023.pdf 78bd962861bd9ff35eb5638726905aaa MD5 1 10259/9317 oai:riubu.ubu.es:10259/9317 2024-07-02 02:05:22.862 Repositorio Institucional de la Universidad de Burgos bubrep@ubu.es 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