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Direction of the Reaction of 6-Methylpyrimidine-2,4(1H,3H)-dione with 2-Chloromethylthiirane: N1- or N3-Thietanyl Derivative?

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Abstract

The reaction of 6-methylpyrimidine-2,41H,3H-dione with 2-chloromethylthiirane gave 6-methyl-N-thietan-3-ylpyrimidine-2,41H,3H-dione. Its oxidation subsequent reaction of the resulting N-1,1-dioxo-λ6-thietan-3-yl derivative with ethyl chloroacetate afforded the corresponding ethyl pyrimidinylacetate. The structure of the latter was determined by X-ray analysis, which confirmed the formation of N3-thietan-3-yl derivative rather than its N1-substituted isomer in the title reaction. According to the results of B3LYP/6-31G++d,p, PBE/3ζ, MP2/6-31G++d,p quantum chemical calculations,the N3-thietanyl derivative is more stable than the N1-isomer. It was also found that the calculated barrier to internal rotation of the thietanyl group about the N–C bond in 6-methyl-3-thietan-3-yl-pyrimidine-2,41H,3H-dione is lower than in the N1-isomer.

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Authors and Affiliations

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

    V. A. Kataev & S. A. Meshcheryakova

  2. Institute of Petrochemistry and Catalysis, Russian Academy of Sciences, pr. Oktyabrya 141, Ufa, 450075 Bashkortostan, Russia

    E. S. Meshcheryakova, T. V. Tyumkina & L. M. Khalilov

  3. Ufa State Aviation Technical University, ul. K. Marksa 12, Ufa, 450008 Bashkortostan, Russia

    V. V. Lazarev & V. V. Kuznetsov

  4. Ufa State Petroleum Technological University, ul. Kosmonavtov 1, Ufa, 450062 Bashkortostan, Russia

    V. V. Kuznetsov

Authors
  1. V. A. Kataev
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  2. S. A. Meshcheryakova
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  3. E. S. Meshcheryakova
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  4. T. V. Tyumkina
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  5. L. M. Khalilov
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  6. V. V. Lazarev
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  7. V. V. Kuznetsov
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Corresponding author

Correspondence to V. V. Kuznetsov.

Additional information

Original Russian Text © V.A. Kataev, S.A. Meshcheryakova, E.S. Meshcheryakova, T.V. Tyumkina, L.M. Khalilov, V.V. Lazarev, V.V. Kuznetsov, 2018, published in Zhurnal Organicheskoi Khimii, 2018, Vol. 54, No. 6, pp. 914–918.

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Kataev, V.A., Meshcheryakova, S.A., Meshcheryakova, E.S. et al. Direction of the Reaction of 6-Methylpyrimidine-2,4(1H,3H)-dione with 2-Chloromethylthiirane: N1- or N3-Thietanyl Derivative?. Russ J Org Chem 54, 918–922 (2018). https://doi.org/10.1134/S1070428018060143

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  • DOI: https://doi.org/10.1134/S1070428018060143

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