Abstract
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%). 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 −40% 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.
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For Communication 5, see [1].
Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 1, pp. 95–102, January, 1989.
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Gulevskaya, A.V., Kuz'menko, V.V., Pozharskii, A.F. et al. Purines, pyrimidines, and condensed systems based on them. Chem Heterocycl Compd 25, 81–88 (1989). https://doi.org/10.1007/BF00472625
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DOI: https://doi.org/10.1007/BF00472625