Oxidation of pyrimidine base derivatives with m-chloroperbenzoic acid.

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  • ChemInform Abstract: Oxidation of Pyrimidine Base Derivatives with m‐Chloroperbenzoic Acid.

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Oxidations of 1, 3-dimethylthymine (1), 3', 5'-diacetylthymidine (2), 1, 3-dimethyluracil (3), 5-fluoro-1, 3-dimethyluracil (4), and 2', 3', 5'-triacetyluridine (5) with m-chloroperbenzoic acid were investigated. Dimethylthymine (1) gave the hydroxy ester (6), the stereostructure of which was determined by an X-ray analysis, while diacetylthymidine (2) gave 10a and 10b. Dimethyluracil (3) provided 11, 12, and 13, and 5-fluoro-dimethyluracil (4) provided 11. Triacetyluridine (5) afforded 16 in dichloromethane and 17 in benzene. A plausible mechanism for formation of these oxidation products is presented.

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