A new synthesis of 5-hydroxy-6-methyluracil |
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Authors: | Stanislav A Grabovskiy Yuri I MurinovNatalia N Kabal’nova |
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Institution: | Institution of the Russian Academy of Science, Institute of Organic Chemistry, Ufa Research Centre of the Russian Academy of Sciences, 71 prosp. Oktyabrya, 450054 Ufa, Russian Federation |
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Abstract: | 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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Keywords: | 5-Hydroxy-6-methyluracil Synthesis Dihydro-5 6-dihydroxy-6-methyluracil Dehydration DFT |
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