Reaction of 2, 3-dihydro-1, 3-6H-oxazine-2, 6-dione with Aliphatic Amines and Amino Acids

…, J Hapala, O Jindrová, J Škoda

Index: Farkas, Jiri; Hapala, Jaroslav; Jindrova, Olga; Skoda, Jan Collection of Czechoslovak Chemical Communications, 1982 , vol. 47, # 11 p. 2932 - 2945

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Abstract

Abstract 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 ...