Metal-Free Synthesis of 2‑(per)Fluoroalkyl-3-nitro Indoles via Intramolecular Cyclization of Amides

Metal-Free Synthesis of 2‑(per)Fluoroalkyl-3-nitro Indoles via Intramolecular Cyclization of Amides

A metal-free intramolecular cyclization of N-acyl amides for the synthesis of 3-nitro-2-(per)­fluoroalkyl indoles is reported. Good functional group tolerance and a broad range of substrates are the features of this approach. The developed method is easy to operate and is suitable for the preparatio...

Ausführliche Beschreibung

Gespeichert in:
Bibliographische Detailangaben
Veröffentlicht in:Journal of organic chemistry 2024-10, Vol.89 (19), p.14028-14037
Hauptverfasser: Sterligov, Grigorii K., Rasskazova, Maria A., Drokin, Egor A., Isaeva, Dilshodakhon K., Ageshina, Alexandra A., Rzhevskiy, Sergey A., Shurupova, Olga V., Topchiy, Maxim A., Minaeva, Lidiya I., Asachenko, Andrey F.
Format: Artikel
Sprache:eng
Schlagworte:
amides
cyclization reactions
indoles
organic chemistry
Online-Zugang:Volltext
Tags: Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
Beschreibung
Zusammenfassung:A metal-free intramolecular cyclization of N-acyl amides for the synthesis of 3-nitro-2-(per)­fluoroalkyl indoles is reported. Good functional group tolerance and a broad range of substrates are the features of this approach. The developed method is easy to operate and is suitable for the preparation of 2-difluoromethyl/trifluoromethyl/perfluoroethyl/perfluoropropyl indoles in yields of 84 to 99%. Also, the application of this protocol in the gram scale is shown.
ISSN:0022-3263
1520-6904
1520-6904
DOI:10.1021/acs.joc.4c01430