Ring cleavage reaction of 1,3-oxazine-2,4(3H)-dione derivatives with amines.

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The reactions of 3, 6-dimethyl [6-methyl-3-phenyl and 3-(4-chlorophenyl)-6-methyl]-1, 3-oxazine-2, 4(3H)-diones (1a, 1b, and 1c) with various amines were investigated under various conditions. Several reaction products were obtained such as the pyrimidines (3a, 3b, 3c, and 3d), the acetoacetamides (4a, 4b, and 4c), (4-chlorophenyl)urethane (5a), and ethyl acetoacetate (4d) with primary amines, and the acetoacetamides (4e and 4f), the urethanes (5a and 5b), the carboxamides (5c, 5d, 5e, and 5f), and the butenamides (7a, 7b, and 7c) with secondary amines. In the case of 1c with amine, alcohol used as a solvent reacted as a nucleophile to give the urethane (5a or 5b).

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