92207-40-4Relevant academic research and scientific papers
Selective Oxidative Halogenation of Uracils
Moltke-Leth, Claus,Joergensen, Karl Anker
, p. 1117 - 1121 (2007/10/02)
A variety of N-substituted uracils has been selectively brominated to the corresponding 5-bromouracils in high yield by CHBr3-O2.Both oxidative bromination and chlorination of N-substituted uracils can be performed by means of combination of haloalkane solvents with m-chloroperbenzoic acid, magnesium monoperoxyphthalate, tert-butyl hydroperoxide or iodosylbenzene.Intermediates along the reaction path leading to the 5-halouracils have been identified; the intermediates depend on the oxidant used.Mechanistic aspects of the halogenation reactions and the reactive intermediates are discussed.
Oxidation of Pyrimidine Base Derivatives with m-Chloroperbenzoic Acid
Harayama, Takashi,Kotoji, Kayoko,Yanada, Reiko,Yoneda, Fumio,Taga, Tooru,et al.
, p. 2354 - 2361 (2007/10/02)
Oxidation 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.Keywords - m-chloroperbenzoic acid oxidation; 1,3-dimethylthymine; 3',5'-diacetylthymidine; 1,3-dimethyluracil; 5-fluoro-1,3-dimethyluracil; 2',3',5'-triacetyluridine; cis-1,3-dimethyl-5,6-dihydroxy-5,6-dihydrothymine
OXIDATION OF 1,3-DIMETHYL DERIVATIVES OF PYRIMIDINE BASES WITH m-CHLOROPERBENZOIC ACID
Harayama, Takashi,Kotoji, Kayoko,Yoneda, Fumio,Taga, Tooru,Osaki, Kenji,Nagamatsu, Tomohisa
, p. 2056 - 2058 (2007/10/02)
Oxidation of 1,3-dimethylthymine (1), 1,3-dimethyluracil (2), and 5-fluoro-1,3-dimethyluracil (3) with m-chloroperbenzoic acid were investigated. 1 gave the cis diol 5,6-dihydrothymine derivative (4) stereoselectively.Its stereostructure was definitely determined by an X-ray analysis. 2 afforded 7, 8, and 9, and 3 afforded 8.KEYWORDS - m-chloroperbenzoic acid oxidation; 1,3-dimethylthymine; 1,3-dimethyluracil; 5-fluoro-1,3-dimethyluracil; cis 5,6-dihydroxy-5,6-dihydrothymine
