title: One-pot three-component synthesis of alpha-iminonitriles by IBX/TBAB-mediated oxidative Strecker reaction.
abstract: The reaction of aldehydes, amines, and TMSCN in the presence of 2-iodoxybenzoic acid (IBX) and tetrabutylammonium bromide (TBAB) afforded alpha-iminonitriles in good to excellent yields under mild conditions. The presence of TBAB is essential for this transformation. The methodology was applied to a two-step synthesis of indolizidine via a microwave-assisted intramolecular cycloaddition of alpha-iminonitrile.
authors.affiliation: Institut de Chimie des Substances Naturelles, Centre National de la Recherche Scientifique, 91198 Gif-sur-Yvette Cedex, France.
authors.forename: Patrice
authors.initials: P
authors.lastname: Fontaine
authors.forename: Angèle
authors.initials: A
authors.lastname: Chiaroni
authors.forename: Géraldine
authors.initials: G
authors.lastname: Masson
authors.forename: Jieping
authors.initials: J
authors.lastname: Zhu
mesh_terms: D003500:Cyclization; D007462:Iodobenzenes; D007463:Iodobenzoates / Q000737:chemistry*; D009570:Nitriles / Q000138:chemical synthesis*; D010084:Oxidation-Reduction; D000644:Quaternary Ammonium Compounds / Q000737:chemistry*
chemical_list: D007462:Iodobenzenes; D007463:Iodobenzoates; D009570:Nitriles; D000644:Quaternary Ammonium Compounds; C476101:o-iodoxybenzoic acid; C009405:tetrabutylammonium