title: One-pot synthesis of polysubstituted indolizines by an addition/cycloaromatization sequence.
abstract: Indolizines carrying various substituents in positions 5-8 were obtained from readily available 2-(1H-pyrrol-1-yl)nitriles and α,β-unsaturated ketones or aldehydes in a one-pot procedure. Michael addition of the deprotonated aminonitriles to the acceptors followed by acid-catalyzed electrophilic cyclization produces 5,6-dihydroindolizine-5-carbonitriles. From these stable intermediates, substituted indolizines were obtained via base-induced dehydrocyanation.
authors.affiliation: Institute of Organic Chemistry, University of Mainz, Duesbergweg 10-14, D-55128 Mainz, Germany.
authors.forename: Murat
authors.initials: M
authors.lastname: Kucukdisli
authors.forename: Till
authors.initials: T
authors.lastname: Opatz
mesh_terms: D000447:Aldehydes / Q000737:chemistry; D003500:Cyclization; D007212:Indolizines / Q000138:chemical synthesis* / Q000737:chemistry; D007659:Ketones / Q000737:chemistry; D015394:Molecular Structure; D009570:Nitriles / Q000737:chemistry
chemical_list: D000447:Aldehydes; D007212:Indolizines; D007659:Ketones; D009570:Nitriles