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 contributionposted on 01.10.2019 by Elena Y. Zelina, Tatyana A. Nevolina, Dmitry A. Skvortsov, Igor V. Trushkov, Maxim G. Uchuskin
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A 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.