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Oxidation and isomerism of thietane-containing heterocycles

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Abstract

Oxidation of 6-methyl-1-(thiethan-3-yl)pyrimidine-2,4(1H,3H)-dione, 5(6)-nitro-1-(thiethan-3-yl)-benzimidazole, 2-methyl-4-nitro-1-(thiethan-3-yl)- and 5-bromo-2-methyl-4-nitro-1-(thiethan-3-yl)imidazoles was examined. Corresponding 1-oxothietan-3-yl- and 1,1-dioxothietan-3-yl derivatives were synthesized for the first time. Some factors affecting the quality of the final products and optimal conditions of the oxidation of thietanyl derivatives of pyrimidine-2,4(1H,3H)-dione, nitrobenzimidazole, and nitroimidazole were found. According to 1H NMR spectroscopy data, the obtained sulfoxides are mixtures of cis/trans isomers, the diastereomers ratio determined by the substituent at position 3 of thietane ring.

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Authors and Affiliations

  1. Bashkir State Medical University, ul. Lenina 3, Ufa, 450000, Russia

    S. A. Meshcheryakova, V. A. Kataev, D. A. Munasipova & I. Ya. Fattakhova

Authors
  1. S. A. Meshcheryakova
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  2. V. A. Kataev
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  3. D. A. Munasipova
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  4. I. Ya. Fattakhova
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Corresponding author

Correspondence to S. A. Meshcheryakova.

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Original Russian Text © S.A. Meshcheryakova, V.A. Kataev, D.A. Munasipova, I.Ya. Fattakhova, 2014, published in Zhurnal Obshchei Khimii, 2014, Vol. 84, No. 5, pp. 773–776.

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Meshcheryakova, S.A., Kataev, V.A., Munasipova, D.A. et al. Oxidation and isomerism of thietane-containing heterocycles. Russ J Gen Chem 84, 865–868 (2014). https://doi.org/10.1134/S1070363214050144

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  • DOI: https://doi.org/10.1134/S1070363214050144

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