Synthesis of novel thiazolidin-4-ones by reaction of malonthioamide derivatives with dimethyl acetylenedicarboxylate

(Note: The full text of this document is currently only available in the PDF Version )

Vera S. Berseneva, Alexey V. Tkachev, Yury Yu. Morzherin, Wim Dehaen, Ingrid Luyten, Suzanne Toppet and Vasiliy A. Bakulev


Abstract

Novel 2,5-dimethylenethiazolidin-4-one derivatives have been prepared by reaction of malonthioamide derivatives with dimethyl acetylenedicarboxylate. These compounds exist as separate (E,Z[hair space])- and (Z,Z[hair space])-isomers or as a mixture. The (E,Z[hair space])-isomer is formed as the initial product which transforms to the (Z,Z[hair space])-isomer under mild conditions. The structures of the obtained compounds have been confirmed by IR and NMR spectroscopy.


References

  1. J. B. Hendrickson, P. Reeds and J. F. Templeton, J. Am. Chem. Soc., 1964, 86, 107 CrossRef CAS.
  2. H. Nagase, Chem. Pharm. Bull., 1973, 21, 270 CAS.
  3. L. I. Giannola, S. Palazzo, P. Agozzino, L. Lamatrina and L. Caraulo, J. Chem. Soc., Perkin Trans. 1, 1978, 1428 RSC.
  4. L. I. Giannola, G. Giammona, S. Palazzo and L. Lamatrina, J. Chem. Soc., Perkin Trans. 1, 1984, 2707 RSC.
  5. V. Ya. Causs, E. E. Liepinsh, I. Ya. Calvinish and E. Ya. Lucevic, Khim. Geterotsikl. Soedin., 1990, 120 Search PubMed.
  6. S. Coen, B. Ragonnet, C. Vieillescazes and J. P. Roggero, Heterocycles, 1985, 23, 1225 CAS.
  7. V. S. Berseneva, N. Yu. Biryucheva and V. A. Bakulev, Khim. Geterotsikl. Soedin., 1993, 1688 Search PubMed.
  8. J. W. Lown and J. C. N. Ma, Can. J. Chem., 1967, 45, 939, 953.
  9. G. Giammona, M. Neri, B. Carlisi, A. Pazzo and C. La Rosa, J. Heterocycl. Chem., 1991, 28, 325 CAS.
  10. L. A. Rodinovskaya, Yu. A. Sharanin, A. M. Shestopalov, V. K. Promonenkov, B. M. Zolotarev and V. Yu. Mortikov, Zh. Org. Khim., 1986, 22, 223.
  11. U. Vojeli, W. Von. Philipsborn, K. Nagarajan and M. D. Nair, Helv. Chim. Acta, 1978, 61, 607 CrossRef.
  12. R. M. Achenson and J. D. Wallis, J. Chem. Soc., Perkin Trans. 1, 1981, 415 RSC.
  13. B. D'hooge and W. Dehaen, Bull. Soc. Chim. Belg., 1997, 106, 729 CAS.
  14. V. A. Bakulev, E. F. Dankova, A. T. Lebeev, V. S. Mokrushin and V. S. Petrosyan, Tetrahedron, 1989, 45, 7329 CrossRef CAS.
Click here to see how this site uses Cookies. View our privacy policy here.