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Heterocyclization of functionalized heterocumulenes with C,N-, C,O, and C,S-binucleophiles: IX. Reaction of 1-aryl-1-chloro-2,2,2-trifluoroethyl isocyanates with sulfanylacetic acid esters as a convenient synthetic route to 2-aryl-2-trifluoromethyl-4-oxo-1,3-thiazolidine-5-carboxylates

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Abstract

1-Aryl-1-chloro-2,2,2-trifluoroethyl isocyanates reacted with methyl and ethyl sulfanylacetates to give the corresponding alkyl 2-aryl-2-trifluoromethyl-4-oxo-1,3-thiazolidine-5-carboxylates.

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References

  1. Vovk, M.V., Sukach, V.A., and Dorokhov, V.I., Russ. J. Org. Chem., 2007, vol. 43, p. 1186.

    Article  CAS  Google Scholar 

  2. Singh, S.P., Parmar, S.S., Ramon, K., and Stenberg, V.I., Chem. Rev., 1981, vol. 81, p. 175.

    Article  CAS  Google Scholar 

  3. Filler, R. and Kobayashi, Y., Biomedicinal Aspects of Fluorine Chemistry, Amsterdam: Elsevier Biomedical, 1982, p. 246.

    Google Scholar 

  4. Filler, R., Kobayashi, Y., and Yagupolski, L.M., Organofluorine Compounds in Medicinal Chemistry and Biomedicinal Applications, Amsterdam: Elsevier, 1993, p. 386.

    Google Scholar 

  5. Schierlinger, C. and Burger, K., Tetrahedron Lett., 1992, vol. 33, p. 193.

    Article  CAS  Google Scholar 

  6. Sewald, N., Seymour, L.C., Burger, K., Osipov, S.N., and Kolomiets, A.F., Tetrahedron: Asymmetry, 1994, vol. 5, p. 1051.

    Article  CAS  Google Scholar 

  7. Reddy, A.C.S., Rao, P.S., and Venkataratnam, R.V., Tetrahedron, 1997, vol. 53, p. 5847.

    Article  CAS  Google Scholar 

  8. Kawase, M., Niwa, M., Nozari, M., and Motohashi, N., Heterocycles, 1998, vol. 48, p. 555.

    Article  CAS  Google Scholar 

  9. Roasch, M.S., J. Heterocycl. Chem., 1974, vol. 11, p. 587.

    Google Scholar 

  10. Sundermeyer, J., Roesky, H.W., Lautner, J., and Jones, P.G., Chem. Ber., 1990, vol. 123, p. 433.

    Article  CAS  Google Scholar 

  11. Vovk, M.V. and Dorokhov, V.I., Zh. Org. Khim., 1993, vol. 29, p. 1772.

    CAS  Google Scholar 

  12. Lebed’, P.S., Vashchuk, A.V., Rusanov, E.B., and Vovk, M.V., Zh. Org. Farm. Khim., 2007, vol. 1, p. 61.

    Google Scholar 

  13. Gorbatenko, V.I. and Samarai, L.I., Synthesis, 1980, no. 2, p. 85.

  14. Fetyukhin, V.I., Koretskii, A.S., Gorbatenko, V.I., and Samarai, L.I., Zh. Org. Khim., 1977, vol. 13, p. 271.

    CAS  Google Scholar 

  15. Sukach, V.A., Chubaruk, N.G., and Vovk, M.V., Russ. J. Org. Chem., 2007, vol. 43, p. 553.

    Article  CAS  Google Scholar 

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Authors and Affiliations

  1. Institute of Organic Chemistry, National Academy of Sciences of Ukraine, ul. Murmanskaya 5, Kiev, 02660, Ukraine

    M. V. Vovk & P. S. Lebed’

  2. Taras Shevchenko Kiev National University, Kiev, Ukraine

    V. V. Polovinko & O. V. Manoilenko

Authors
  1. M. V. Vovk
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  2. P. S. Lebed’
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  3. V. V. Polovinko
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  4. O. V. Manoilenko
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Corresponding author

Correspondence to M. V. Vovk.

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Original Russian Text © M.V. Vovk, P.S. Lebed’, V.V. Polovinko, O.V. Manoilenko, 2008, published in Zhurnal Organicheskoi Khimii, 2008, Vol. 44, No. 12, pp. 1862–1865.

For communication VIII, see [1].

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Vovk, M.V., Lebed’, P.S., Polovinko, V.V. et al. Heterocyclization of functionalized heterocumulenes with C,N-, C,O, and C,S-binucleophiles: IX. Reaction of 1-aryl-1-chloro-2,2,2-trifluoroethyl isocyanates with sulfanylacetic acid esters as a convenient synthetic route to 2-aryl-2-trifluoromethyl-4-oxo-1,3-thiazolidine-5-carboxylates. Russ J Org Chem 44, 1836–1839 (2008). https://doi.org/10.1134/S107042800812021X

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  • DOI: https://doi.org/10.1134/S107042800812021X

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