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4-Acyl-2H-thiopyran-3,5(4H,6H)-diones: Synthesis, Oxidation, and Reaction with Amines

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Abstract

Acylation of 2H-thiopyran-3,5(4H,6H)-dione and 2-methyl-2H-thiopyran-3,5(4H,6H)-dione with acetyl chloride or propionyl chloride afforded the corresponding 4-acyl-2H-thiopyran-3,5(4H,6H)-diones. Oxidation of 4-acetyl-2H-thiopyran-3,5(4H,6H)-dione with m-chloroperoxybenzoic acid gave 4-acetyl-2H-thiopyran-3,5(4H,6H)-dione 1-oxide. 4-Acyl-2H-thiopyran-3,5(4H,6H)-diones and 4-acetyl-2H-thiopyran-3,5(4H,6H)-dione 1-oxide reacted with pyrrolidine, allylamine, and p-anisidine, resulting in formation of the corresponding 4-aminomethylene derivatives.

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Authors and Affiliations

  1. Institute of Bioorganic Chemistry, National Academy of Sciences of Belarus, ul. Kuprevicha 5/2, Minsk, 220141, Belarus

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

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  1. T. A. Zheldakova
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  2. M. V. Budnikova
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  3. I. L. Rubinova
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  4. D. B. Rubinov
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Zheldakova, T.A., Budnikova, M.V., Rubinova, I.L. et al. 4-Acyl-2H-thiopyran-3,5(4H,6H)-diones: Synthesis, Oxidation, and Reaction with Amines. Russian Journal of Organic Chemistry 39, 1772–1776 (2003). https://doi.org/10.1023/B:RUJO.0000019742.81245.f7

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  • DOI: https://doi.org/10.1023/B:RUJO.0000019742.81245.f7

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