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A New Route to N1-Substituted Uracil Derivatives Using Hypervalent Iodine
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2012
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Combinatorial ChemistryBioorganic ChemistryEngineeringNovel Glycosylation ReactionOrganic ChemistryChemistryChemical DerivativeNew RouteMedicinal ChemistryStereoselective SynthesisCross-coupling ReactionDerivativesDiversity-oriented SynthesisNatural Product SynthesisPersilylated UracilBiomolecular EngineeringOxidative Coupling ReactionNatural SciencesDerivative (Chemistry)Synthetic Chemistry
In continuation of our previous study, oxidative coupling reactions of uracil with allylsilane or enol ethers were examined using diacetoxyiodobenzene. The reaction of persilylated uracil with 3,4-dihydro-2<i>H</i>-pyran in the presence of TMSOTf and PhI(OAc)<sub>2</sub> resulted in the formation of a dihydropyranyluracil derivative, although the yield was low. In an extension of the oxidative coupling reaction, a novel glycosylation reaction using glycal derivatives as substrates was also developed. The treatment of persilylated uracil and 3,4-dihydro-2<i>H</i>-pyran with (PhSe)<sub>2</sub> and PhI(OAc)<sub>2</sub> in the presence of a catalytic amount of TMSOTf gave a 2,3-<i>anti</i>-derivative of 1-(3-phenylselanyltetrahydropyran-2-yl)uracil stereoselectively and in good yield.