One-pot synthesis of nitrones from primary amines and aldehydes catalyzed by methyltrioxorhenium.
One-pot condensation/oxidation of primary amines and aldehydes using urea-hydrogen peroxide (UHP) as the stoichiometric oxidant in the presence of methyltrioxorhenium (MTO) as catalyst affords nitrones in a simple and regioselective manner. UHP is a practical and safe source of H2O2, and its use here instead of aqueous H2O2 solutions also simplifies greatly the workup procedure as extractions with organic solvents can be avoided. Typically, at the end of the reaction the solid urea is simply filtered off. From a sustainability point of view, this one-pot synthesis is simple to perform, takes place under mild conditions, has a high atom economy, and releases water as the only by-product.
Cardona
Francesca
F
Department of Organic Chemistry U. Schiff Laboratory of Design, Synthesis and Study of Biologically Active Heterocycles (HeteroBioLab), University of Florence, Sesto Fiorentino, Italy.
Bonanni
Marco
M
Soldaini
Gianluca
G
Goti
Andrea
A
D000447:Aldehydes / Q000737:chemistry*; D000588:Amines / Q000737:chemistry*; D002384:Catalysis; D006861:Hydrogen Peroxide / Q000737:chemistry; D009589:Nitrogen Oxides / Q000138:chemical synthesis* / Q000737:chemistry; D009942:Organometallic Compounds / Q000737:chemistry*; D010084:Oxidation-Reduction; D013237:Stereoisomerism; D013379:Substrate Specificity; D014508:Urea / Q000737:chemistry
D000447:Aldehydes; D000588:Amines; D009589:Nitrogen Oxides; D009942:Organometallic Compounds; C015388:nitrones; C411866:methyltrioxorhenium VII; D014508:Urea; D006861:Hydrogen Peroxide