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Synthesis of Enol Methyl Ethers of 3-Acetyl-6,6-dimethyltetrahydrothiopyran-2,4-dione and Their Reactions with Amines

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Abstract

The reaction of 3-acetyl-6,6-dimethyltetrahydrothiopyran-2,4-dione with diazomethane furnishes a mixture of 3-acetyl-6,6-dimethyl-4-methoxy-5,6-dihydro-2H-thiopyran-2-one and 3-acetyl-6,6-dimethyl- 2-methoxy-5,6-dihydro-2H-thiopyran-4-one in 2:3 ratio, whereas in reaction with dimethyl sulfate in the presence of potassium carbonate forms a mixture of the same products in 9:1 ratio. In both reactions the overall yield of ethers amounts to 50%. Treating of regioisomeric enol methyl ethers with pyrrolidine, o-toluidine, and allylamine provides the corresponding endocyclic enaminodiketones.

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Authors and Affiliations

  1. Institute of Bioorganic Chemistry, Belorussian Academy of Sciences, Minsk, 220141, Belarus

    T. A. Zheldakova, M. V. Budnikova & D. B. Rubinov

Authors
  1. T. A. Zheldakova
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  2. M. V. Budnikova
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  3. D. B. Rubinov
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Zheldakova, T.A., Budnikova, M.V. & Rubinov, D.B. Synthesis of Enol Methyl Ethers of 3-Acetyl-6,6-dimethyltetrahydrothiopyran-2,4-dione and Their Reactions with Amines. Russian Journal of Organic Chemistry 39, 235–241 (2003). https://doi.org/10.1023/A:1025544404200

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  • DOI: https://doi.org/10.1023/A:1025544404200

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