Comparison of electrophilic amination reagents for N-amination of 2-oxazolidinones and application to synthesis of chiral hydrazones.
Comparison of several hydroxylamine-based electrophilic ammonia equivalents in the N-amination of 2-oxazolidinones revealed that O-(p-nitrobenzoyl)hydroxylamine (NbzONH(2)) and sodium hydride in dioxane is a superior reagent combination for this purpose. Practical preparations of a variety of chiral N-acylhydrazones by this method gave yields ranging from 45 to 95%. Methods for exchange or removal of the aldehyde component have been developed, making this a general route to chiral N-acylhydrazones of interest for asymmetric synthesis applications.
Department of Chemistry, Cook Physical Science Building, University of Vermont, Burlington, Vermont 05405, USA.
Yuehai
Y
Shen
Gregory K
GK
Friestad
D000586:Amination; D000588:Amines / Q000737:chemistry*; D002384:Catalysis; D002625:Chemistry, Organic / Q000379:methods*; D002855:Chromatography, Thin Layer; D006571:Heterocyclic Compounds; D006835:Hydrazones / Q000138:chemical synthesis*; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D023303:Oxazolidinones / Q000737:chemistry*; D013237:Stereoisomerism
D000588:Amines; D006571:Heterocyclic Compounds; D006835:Hydrazones; D023303:Oxazolidinones