jo9b01925_si_001.pdf (10.82 MB)
A Route to (Het)arene-Annulated Pyrrolo[1,2‑d][1,4]diazepines via the Expanded Intramolecular Paal–Knorr Reaction: Nitro Group and Furan Ring as Equivalents of Amino Group and 1,4-Diketone
journal contribution
posted on 2019-10-01, 19:38 authored by Elena
Y. Zelina, Tatyana A. Nevolina, Dmitry A. Skvortsov, Igor V. Trushkov, Maxim G. UchuskinA straightforward
protocol toward pharmacologically relevant (het)areno[x,y-b]pyrrolo[1,2-d][1,4]diazepines in good to high yields has been described.
The designed approach consists of an acid-promoted furan ring opening
in easily accessible N-(2-furylethyl)-2-nitroanilines
or their heterocyclic analogues followed by the reductive cyclization
of the corresponding nitro-1,4-diketones.