2026-06-17T23:46:47Zhttps://riubu.ubu.es/oai/request

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

00925njm 22002777a 4500 dc Gómez Gil, Sara author Solas Luera, Marta author Suarez Pantiga, Samuel author Sanz Díez, Roberto author 2023-12-12 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. 0022-3263 http://hdl.handle.net/10259/9317 10.1021/acs.joc.3c02248 1520-6904 Brønsted Acid-Catalyzed Synthesis of 4-Functionalized Tetrahydrocarbazol-1-ones from 1,4-Dicarbonylindole Derivatives