2026-05-14T11:35:45Zhttps://riubu.ubu.es/oai/requestoai:riubu.ubu.es:10259/93172024-07-02T00:05:22Zcom_10259_3593com_10259_5086com_10259_2604col_10259_3594
Repositorio Institucional de la Universidad de Burgos
author
Gómez Gil, Sara
author
Solas Luera, Marta
author
Suarez Pantiga, Samuel
author
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.
eng
Atribución 4.0 Internacional
Brønsted Acid-Catalyzed Synthesis of 4-Functionalized Tetrahydrocarbazol-1-ones from 1,4-Dicarbonylindole Derivatives
info:eu-repo/semantics/article
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URL
https://riubu.ubu.es/bitstream/10259/9317/1/Gomez-joc_2023.pdf
File
MD5
78bd962861bd9ff35eb5638726905aaa
2657196
application/pdf
Gomez-joc_2023.pdf