SYNTHESIS OF OPTICALLY ACTIVE 5-THIOXOTETRAHYDRO-5<i>H</i>-OXAZOLO[3,2-<i>c</i>]PYRIMIDIN-2(3<i>H</i>)ONES

Authors

  • Ulyana M. Aristova Samara State Technical University, 244 Molodogvardeyskaya St., Samara 443100, Russia
  • Anna V. Vologzhanina A. N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, 28 Vavilov St., Moscow 119334, Russia
  • Andrey K. Shiryaev Samara State Technical University, 244 Molodogvardeyskaya St., Samara 443100, Russia

DOI:

https://doi.org/10.1007/7780

Keywords:

amino acid, oxazolopyrimidine, pyrimidine, diastereoselectivity, optical rotation.

Abstract

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.

Author Biography

Ulyana M. Aristova, Samara State Technical University, 244 Molodogvardeyskaya St., Samara 443100, Russia

доктор химических наук, профессор, Кафедра органической химии

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Published

2023-11-01

Issue

Vol. 59 No. 9/10 (2023)

Section

Original Papers