Stanislav Grabovskiy - A new synthesis of 5-hydroxy-6-methyluracil

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      Publication Details (including relevant citation   information):

        Tetrahedron Letters, 2012, 53 (45), pp. 6025-6028.  


      Dehydration of   5,6-dihydro-5,6-dihydroxy-6-methyl- and 5,6-dihydro-5,6-   dihydroxy-1,3,6-trimethyl-uracil in 0.4 M aqueous sulfuric acid   gives 5-hydroxy-6-methyl- and 5-hydroxy-1,3,6-trimethyluracil in   quantitative yields. Two possible mechanisms have been examined   using the mPW1k/6-311+G(2df,2pd)// mPW1k/6-31+G(d,p) method for   the transformation of methylated and non-methylated   5,6-dihydro-5,6-dihydroxy-6-methyluracils into the corresponding   5-hydroxy-6-methyluracils. The first is a hydride C5-C6 shift   occurring in concert with the loss of a water molecule and   formation of the corresponding protonated   5,6-dihydro-5-oxo-6-methyluracils. The second is an   acid-catalyzed dehydration reaction to yield   5-hydroxy-6-methyluracils. The calculations demonstrated that the   second pathway was energetically most favorable

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