Synthesis of N‑Functionalized/NH-Multisubstituted
Indoles, Thienopyrroles, Pyrroloindoles, and Pyrazolopyrroles via
Sequential One-Pot Base-Mediated and Copper-Catalyzed Inter- and Intramolecular
Amination of 2‑[2-Bromo(het)aryl]-3-(het)aryl-3-(methylthio)acrylonitriles
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Abstract
A novel,
efficient route to substituted 1-<i>N</i>-(het)aryl/NH-2-(het)aryl-3-cyanoindoles
and related pyrrolo-fused heterocycles such as thienopyrroles, pyrroloindoles,
and pyrazolopyrroles has been reported. The overall protocol involves
sequential cycloamination of readily available 2-[2-bromo(het)aryl]-3-(het)aryl-3-(methylthio)acrylonitrile
precursors with primary amines or amides via two key C–N bond-forming
processes, one base-mediated intermolecular and the other Cu-catalyzed
intramolecular arylamination leading to N(1)–C(2) and N(1)–C(7a)
bond formation, respectively, in a two-step one-pot procedure