RT info:eu-repo/semantics/article
T1 Brønsted Acid-Catalyzed Synthesis of 4-Functionalized Tetrahydrocarbazol-1-ones from 1,4-Dicarbonylindole Derivatives
A1 Gómez Gil, Sara
A1 Solas Luera, Marta
A1 Suárez Pantiga, Samuel
A1 Sanz Díez, Roberto
K1 Química orgánica
K1 Chemistry, Organic
AB 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.
PB ACS Publications
SN 0022-3263
YR 2023
FD 2023-12-12
LK http://hdl.handle.net/10259/9317
UL http://hdl.handle.net/10259/9317
LA eng
NO 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.
DS Repositorio Institucional de la Universidad de Burgos
RD 11-dic-2024