Collect. Czech. Chem. Commun. 1982, 47, 2932-2945

Reaction of 2,3-dihydro-1,3-6H-oxazine-2,6-dione with aliphatic amines and amino acids

Jiří Farkaš, Jaroslav Hapala, Olga Jindrová and Jan Škoda

Institute of Organic Chemistry and Biochemistry, Czechoslovak Academy of Sciences, 166 10 Prague 6


Reaction of 2,3-dihydro-1,3-6H-oxazine-2,6-dione (I) with amines in aqueous medium leads predominantly to N-substituted amides of (Z)-3-carboxylamino-2-propenoic acid. Isomeric 3-(N'-alkylureido)-2-propenoic acids are formed as by-products in the reaction of compound I with ammonia or methylamine; tert-butylamine affords ureido derivative as the sole reaction product. Secondary amines react with compound I substantially more rapidly than primary amines. In both cases the branching on the α-carbon decreases the reactivity distinctly while the branching on the β-carbon does not have a significant effect on the rate of aminolysis. The results of kinetic measurements of the reaction of compound I with amino acids are discussed n connection with the possible interaction of compound I with enzymes.