Russian Journal of Organic Chemistry

, Volume 42, Issue 7, pp 1036–1038 | Cite as

Rearrangement with oxide ion transfer in reactions of 4-chloro-2-oxo-2,3-dihydrothiazole-5-carbaldehyde with ureas. cis-(Z)-trans-(E) isomerism of N-(2,4-dioxothiazolidin-5-ylidenemethyl)ureas

  • N. V. Spitsyn
  • A. N. Vdovichenko


4-Chloro-2-oxo-2,3-dihydrothiazole-5-carbaldehyde reacted with monosubstituted ureas to give cis-(Z)-and trans-(E)-N-(2,4-dioxothiazolidin-5-ylidenemethyl)ureas via rearrangement involving oxide ion transfer, cis (Z) Isomers were formed in methanol or dimethylformamide, while both individual cis (Z) and trans (E) isomers and their mixtures were isolated in the reaction performed in acetic acid.


Oxide Acetic Methanol Urea Acetic Acid 
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  1. 1.
    Schulte, K.E., Reisch, J., and Stoes, V., Angew. Chem., 1965, vol. 24, p. 1141.Google Scholar
  2. 2.
    Rylski, L., Sorm, F., and Arnold, Z., Collect. Czech. Chem. Commun., 1959, vol. 24, p. 1667.Google Scholar
  3. 3.
    Gragerov, I.P., Pogorelyi, V.K., and Franchuk, I.F., Vodorodnaya svyaz’ i bystryi protonnyi obmen (Hydrogen Bond and Fast Proton Exchange), Kiev: Naukova Dumka, 1978, p. 21.Google Scholar
  4. 4.
    Kopteva, T.S. and Shigorin, D.N., Zh. Fiz. Khim., 1974, vol. 48, p. 532.Google Scholar
  5. 5.
    Baranov, S.N., Kochkanyan, R.O., Zaritovskii, A.N., Belova, G.I., and Radkova, S.S., Khim. Geterotsikl. Soedin., 1975, p. 85.Google Scholar
  6. 6.
    Kurzer, F., Org. Synth., 1963, collect. vol. 4, p. 49.Google Scholar

Copyright information

© Pleiades Publishing, Inc. 2006

Authors and Affiliations

  • N. V. Spitsyn
    • 1
  • A. N. Vdovichenko
    • 1
  1. 1.Litvinenko Institute of Physical Organic and Coal ChemistryNational Academy of Sciences of UkraineDonetskUkraine

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