Norris, Peter published the artcileDevelopment of reactions of 6- and 5-substituted 1,3-dimethyluracils with dimethylsulfoxonium methylide, Application In Synthesis of 5034-06-0, the publication is Journal of Organic Chemistry (1999), 64(20), 7290-7298, database is CAplus.
6-Chloro-1,3-dimethyluracil reacts with dimethylsulfoxonium methylide, MeS(:O):CH2, to give sulfoxonium ylide I in 51% yield. The structure of I was established spectroscopically and by its reactions with various electrophiles and electron-deficient olefins. Thus, I is converted by HCl to a sulfoxonium chloride which then yields 6-(chloromethyl)-1,3-dimethyluracil (II) by heating in MeCN. I undergoes deuterium exchange at the 5-position, at its methine carbon, and into its Me groups attached to sulfur. Reaction of I with BzCl gives the highly substituted ylide III or the nucleophilic substitution products II and (α-chlorophenacyl)uracil IV, depending on reaction conditions. Treatment of I with electron-deficient olefins yields 6-cyclopropyluracils, e.g. V. Many of the cyclopropyluracils were converted to trans-1-(1,3-dimethyluracilyl)-2-vinylcyclopropanes and cycloheptenyluracils. Reaction 5-(phenylsulfinyl)-1,3-dimethyluracil with MeS(:O):CH2 yields cyclothymine VI, whereas reaction of 5-phenylseleninyl-1,3-dimethyluracil with MeS(:O):CH2 gave I as the major product.
Journal of Organic Chemistry published new progress about 5034-06-0. 5034-06-0 belongs to chlorides-buliding-blocks, auxiliary class Salt,Aliphatic hydrocarbon chain, name is trimethyloxosulphonium chloride, and the molecular formula is C3H9ClOS, Application In Synthesis of 5034-06-0.
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