PURINES, PYRIMIDINES, AND CONDENSED SYSTEMS BASED ON THEM. 6. REACTIVITY OF 7- AND 9-AMINOXANTHINES TOWARD OXIDIZING AGENTS AND SOME ELECTROPHILES. SYNTHESIS OF THE ANTIBIOTICS FERVENULIN AND RHEUMYCIN

Article abstract of DOI:10.1007/BF00472625

The action of various oxidizing agents on 7- and 9-aminotheophyllines and also on 1-methyl-9-aminoxanthine was studied. 7-Aminotheophyllines are oxidized by almost all the oxidizing agents to 6,8-dimethylpyrimido<4,5-e>-as-triazine-5,7(6H,8H)-dione (40-90 percent). 1-Methyl-9-aminoxanthine and 9-aminotheophylline are oxidized with greater difficulty.The best results are obtained with hydrogen peroxide, which transforms these amines with yields of ca. 40 percent into the antibiotics rheumycin and fervenulin, respectively.Under certain conditions the action of bromine and nitric acid leads to the bromination and nitration of the N-aminoxanthines at position 8.A series of the physicochemical characteristics of the N-aminoxanthines were investigated.The factors which affect their behavior toward oxidizing agents and electrophiles are discussed.