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.

Autor: Vijay Kumar S; New Chemistry Unit, Jawaharlal Nehru Centre for Advanced Scientific Research , Jakkur, Bangalore 560064, India., Saraiah B, Parameshwarappa G, Ila H, Verma GK
Jazyk: angličtina
Zdroj: The Journal of organic chemistry [J Org Chem] 2014 Sep 05; Vol. 79 (17), pp. 7961-78. Date of Electronic Publication: 2014 Aug 07.
DOI: 10.1021/jo501114a
Abstrakt: A novel, efficient route to substituted 1-N-(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.
Databáze: MEDLINE