2026-06-20T14:23:33Zhttps://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 Solas Luera, Marta Suarez Pantiga, Samuel Sanz Díez, Roberto 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