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

• Published in: Journal of organic chemistry Vol. 84; no. 21; pp. 13707 - 13720
• Main Authors: Zelina, Elena Y, Nevolina, Tatyana A, Skvortsov, Dmitry A, Trushkov, Igor V, Uchuskin, Maxim G
• Format: Journal Article
• Language: English
• Published: WASHINGTON American Chemical Society 01.11.2019; Amer Chemical Soc
• Subjects: chemical reactions; chemical structure; Chemistry; Chemistry, Organic; furans; nitro compounds; Physical Sciences; Science & Technology; THERAPEUTIC EFFICACY; PHARMACOKINETIC PROPERTIES; BROMOPYRROLE ALKALOIDS; PYRROLIZINES; DERIVATIVES

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 heterocycl...