One-pot three-component synthesis of alpha-iminonitriles by IBX/TBAB-mediated oxidative Strecker reaction.
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.
Fontaine
Patrice
P
Institut de Chimie des Substances Naturelles, Centre National de la Recherche Scientifique, 91198 Gif-sur-Yvette Cedex, France.
Chiaroni
Angèle
A
Masson
Géraldine
G
Zhu
Jieping
J
D003500:Cyclization; D007462:Iodobenzenes; D007463:Iodobenzoates / Q000737:chemistry*; D009570:Nitriles / Q000138:chemical synthesis*; D010084:Oxidation-Reduction; D000644:Quaternary Ammonium Compounds / Q000737:chemistry*
D007462:Iodobenzenes; D007463:Iodobenzoates; D009570:Nitriles; D000644:Quaternary Ammonium Compounds; C476101:o-iodoxybenzoic acid; C009405:tetrabutylammonium