title: Solid-phase synthesis of 2-aryl-3-alkylamino-1H-indoles from 2-nitro-N-(2-oxo-2-arylethyl)benzenesulfonamides via base-mediated C-arylation.
abstract: Polymer-supported 2-nitro-N-(2-oxo-2-arylethyl)benzenesulfonamides, prepared from resin-bound amines by sulfonylation with 2-nitrobenzenesulfonyl chlorides followed by alkylation with α-bromoacetophenones, represent advanced intermediates for the synthesis of different nitrogenous heterocycles. We report their application for the synthesis of 2-aryl-3-alkylamino-1H-indoles via base-mediated C-arylation reactions followed by the reduction of the C-arylated intermediates. Linear precursors for C-arylation were prepared on solid-phase support from simple, commercially available building blocks. The effects of different substituents on the amino and aryl groups were addressed.
authors.affiliation: Department of Organic Chemistry, Faculty of Science, Palacký University , 17. Listopadu 12, 771 46 Olomouc, Czech Republic.
authors.forename: Eva
authors.initials: E
authors.lastname: Schütznerová
authors.forename: Viktor
authors.initials: V
authors.lastname: Krchňák
mesh_terms: D003500:Cyclization; D007211:Indoles / Q000138:chemical synthesis* / Q000737:chemistry*; D015394:Molecular Structure; D013449:Sulfonamides / Q000737:chemistry*
chemical_list: D007211:Indoles; D013449:Sulfonamides
keywords: C-arylation; advanced intermediates; heterocycles; indoles; solid-phase synthesis