M. D’hooghe, Andries Van Nieuwenhove, Willem Van Brabandt
Feb 4, 2008
Citations
0
Influential Citations
13
Citations
Journal
Tetrahedron
Abstract
Abstract 1-Arylmethyl-2-(bromomethyl)aziridines were transformed into 2-[ N -(arylmethyl)amino]pentanedinitriles upon treatment with an excess of potassium cyanide in DMSO through an unprecedented and peculiar reaction mechanism, involving base-induced ring opening of intermediate 2-(cyanomethyl)aziridines into allylamines, followed by migration of the double bond out of the conjugation towards aldimines via enamine intermediates. The resulting aminopentanedinitriles served as substrates for the synthesis of novel 2-imino-5-methoxypyrrolidines upon treatment with sodium methoxide in methanol, which were either acetylated at the free imino group to afford the more stable N -acetylimino derivatives or hydrolyzed towards the corresponding synthetically relevant 5-methoxypyrrolidin-2-ones.