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

Zelina, Elena
Y.; Nevolina, Tatyana A.; Skvortsov, Dmitry A.; Trushkov, Igor V.; Uchuskin, Maxim G.

doi:10.1021/acs.joc.9b01925.s001

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

https://doi.org/10.1021/acs.joc.9b01925.s001
Open external identifier URL

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. Uchuskin

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.