Fused 1,3-Oxazine Derivatives. Synthesis of 2H-1,3-Oxazino [5,6-b]-quinoxaline-2,4 (3H)-diones (1-Oxaalloxazines), 2H-1,3-Oxazino-[6,5-b] quinoline-2,4 (3H)-diones (5-Deaza-1-oxaalloxazines), and 2H-Pyrido [3,2-e]-1,3-oxazine-2,4 (3H)-diones

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Reactions of 6-anilino-3-methyl-2H-1,3-oxazine-2,4 (3H)-diones (1) with triethyl orthoformate, N, N-dimethylformamide dimethyl acetal, diethyl azodicarboxylate, and dimethyl acetylene-dicarboxylate were carried out with the aim of synthesizing fused-ring 1,3-oxazine derivatives 3-Methyl-2H-1,3-oxazino [6,5-b] quinoline-2,4 (3H)-dione (3-methyl-5-deaza-1-oxaalloxazine) (2) and 3-methyl-2H-1,3-oxazino [5,6-b] quinoxaline-2,4 (3H)-dione (3-methyl-1-oxaalloxazine) (8) were obtained by the reactions of the 6-anilinooxazine (1a) with triethyl orthoformate and diethyl azodicarboxylate, respectively. Treatment of 1a with dimethyl acetylenedicarboxylate gave methyl 3-methyl-2,4,7-trioxo-8-phenyl-3,4,7,8-tetrahydro-2H-pyrido [3,2-e]-1,3-oxazine-5-carboxylate (9a) as well as methyl 1-methyl-2,5-dioxo-1,2,5,10-tetrahydrobenzo [b] [1,8] naphthyridine-4-carboxylate (10) as a ring transformation product. The 6-(p-anisidino)-(1b) and the 6-(3,4-xylidino)-oxazine (1c) also gave the corresponding pyrido [3,2-e]-1,3-oxazines (9b) and (9c).

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