title: 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.
abstract: 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.
authors: New Chemistry Unit, Jawaharlal Nehru Centre for Advanced Scientific Research , Jakkur, Bangalore 560064, India.
authors: S
authors: S
authors: Vijay Kumar
authors: B
authors: B
authors: Saraiah
authors: G
authors: G
authors: Parameshwarappa
authors: H
authors: H
authors: Ila
authors: Girijesh K
authors: GK
authors: Verma
mesh_terms: D000181:Acrylonitrile / Q000031:analogs & derivatives / Q000138:chemical synthesis* / Q000737:chemistry; D000586:Amination; D002384:Catalysis; D003300:Copper / Q000737:chemistry*; D007211:Indoles / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D011758:Pyrroles / Q000138:chemical synthesis* / Q000737:chemistry
chemical_list: D007211:Indoles; D011758:Pyrroles; C521801:thienopyrrole; D003300:Copper; D000181:Acrylonitrile