Studies on Heterocyclic Compounds. XXXII. Synthesis of 8-Substituted Theophyllines from 6-Amino-5-benzylideneamino-1, 3-dimethyluracils with Nickel Peroxide

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Oxidation of 6-amino-5-benzylideneamino-1, 3-dimethyluracils (Ia-e) with nickel peroxide (Ni-PO) in dimethylsulfoxide (DMSO) afforded 8-substituted theophyllines (IIa-e) and dimethylsulfone. Ni-PO oxidation of the Schiff base acetate (V) of 5, 6-diamino-1, 3-dimethyluracil with D-glucose did not give a nucleoside analog ; in stead, 1, 3, 7, 9-tetramethyl-2, 4, 6, 8-(1H, 3H, 7H, 9H)pyrimido[5, 4-g]pteridinetetrone (VI) and penta-O-acetylgluconic acid were obtained. The reaction mechanisms of Ni-PO and the Schiff bases (Ia-e, V) are discussed.