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Synthesis of optically active 5-thioxotetrahydro-5H-oxazolo[3,2-c]pyrimidin-2(3H)ones

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Chemistry of Heterocyclic Compounds Aims and scope

5-Thioxotetrahydro-5H-oxazolo[3,2-c]pyrimidin-2(3H)-ones were prepared by the reaction of L- and D-amino acid esters with 4-isothiocyanato-4-methylpentan-2-one at room temperature. The configuration of products was confirmed by the comparison of optical rotary power calculated according to time-dependent DFT with experimental values and by X-ray analysis. The mechanism of the reaction has been discussed.

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The work was performed using the scientific equipment of the Center for Collective Use “Investigation of the physicochemical properties of substances and materials” of Samara State Technical University.

The X-ray structural studies were supported by the Ministry of Science and Higher Education of the Russian Federation (contract No. 075-03-2023-642) and were performed using the equipment of Center for molecular composition studies of INEOS RAS.

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Authors and Affiliations

  1. Samara State Technical University, 244 Molodogvardeyskaya St., Samara, 443100, Russia

    Ulyana M. Aristova & Andrey K. Shiryaev

  2. A. N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, 28 Vavilov St., Moscow, 119334, Russia

    Anna V. Vologzhanina

Authors
  1. Ulyana M. Aristova
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  2. Anna V. Vologzhanina
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  3. Andrey K. Shiryaev
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Correspondence to Andrey K. Shiryaev.

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Published in Khimiya Geterotsiklicheskikh Soedinenii, 2023, 59(9/10), 698–702

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Aristova, U.M., Vologzhanina, A.V. & Shiryaev, A.K. Synthesis of optically active 5-thioxotetrahydro-5H-oxazolo[3,2-c]pyrimidin-2(3H)ones. Chem Heterocycl Comp 59, 698–702 (2023). https://doi.org/10.1007/s10593-023-03256-1

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  • DOI: https://doi.org/10.1007/s10593-023-03256-1

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