Chemistry of Heterocyclic Compounds

, Volume 50, Issue 6, pp 888–900 | Cite as

Reaction of Enamines and Azaenamines Containing a Thioamide Group with Dimethyl Acetylenedicarboxylate

  • N. P. Belskaya
  • K. I. Lugovik
  • A. D. Ivina
  • V. A. Bakulev
  • Z. J. Fan

The reaction between enamines and azaenamines containing a thioamide group and dimethyl acetylenedicarboxylate was studied under various conditions. It was shown that exchanging one of the carbon atoms in the structure of the investigated compounds for a nitrogen atom significantly affected the reactivity. Functionalized thiopyrans and thiazolidinones were obtained during this investigation.


azaenamines dimethyl acetylenedicarboxylate enamines thiazolidinones thiopyrans cycloaddition cyclocondensation 


  1. 1.
    N. A. Danilkina, L. E. Mikhailov, and B. A. Ivin, Zh. Org. Khim., 42, 807 (2006). [Russ. J. Org. Chem., 42, 783 (2006).]CrossRefGoogle Scholar
  2. 2.
    V. N. Britsun and M. O. Lozinskii, Khim. Geterotsikl. Soedin., 43, 1283 (2007). [Chem. Heterocycl. Compd., 43, 1083 (2007).]CrossRefGoogle Scholar
  3. 3.
    T. G. Deryabina, M. A. Demina, N. P. Belskaya, and V. A. Bakulev, Izv. Akad. Nauk, Ser. Khim., 2784 (2005). [Russ. Chem. Bull., 54, 2880 (2005).]CrossRefGoogle Scholar
  4. 4.
    J. Bloxham and C. P. Dell, J. Chem. Soc., Perkin Trans. 1, 989 (1994).Google Scholar
  5. 5.
    G. T. Manh, H. Bakkali, L. Maingot, M. Pipelier, U. Joshi, J. P. Pradere, S. Sabelle, R. Tuloup, and D. Dubreuil, Tetrahedron Lett., 45, 5913 (2004).CrossRefGoogle Scholar
  6. 6.
    A. Marwaha, V. Sudan, and M. P. Mahajan, Heterocycles, 76, 1087 (2008).CrossRefGoogle Scholar
  7. 7.
    A. A. Hassan, Y. R. Ibrahim, A. A. Aly, E. M. El-Sheref, and T. Yamato, J. Heterocycl. Chem., 50, 473 (2013).CrossRefGoogle Scholar
  8. 8.
    K. L. Obydennov, E. L. Klimareva, M. F. Kosterina, P. A. Slepukhin, and Yu. Yu. Morzherin, Tetrahedron Lett., 54, 4876 (2013).CrossRefGoogle Scholar
  9. 9.
    K. L. Obydennov, M. F. Kosterina, E. L. Klimareva, V. A. Bakulev, and Yu. Yu. Morzherin, Izv. Akad. Nauk, Ser. Khim., 991 (2011). [Russ. Chem. Bull., 60, 1016 (2011).]CrossRefGoogle Scholar
  10. 10.
    M. F. Kosterina, T. V. Rybalova, Yu. V. Gatilov, and Yu. Yu. Morzherin, Khim. Geterotsikl. Soedin., 541 (2009). [Chem. Heterocycl. Compd., 45, 422 (2009).]CrossRefGoogle Scholar
  11. 11.
    A. Darehkordi, K. Saidi, and M. R. Islami, ARKIVOC, i, 180 (2007).Google Scholar
  12. 12.
    M. M. Heravi, N. Nami, H. A. Oskooie, R. Hekmatshoar, and Z. Jaddi, Phosphorus, Sulfur Silicon Relat. Elem., 181, 87 (2006).CrossRefGoogle Scholar
  13. 13.
    V. A. Bakulev, V. S. Berseneva, N. P. Belskaia, Yu. Yu. Morzherin, A. Zaitsev, W. Dehaen, I. Luyten, and S. Toppet, Org. Biomol. Chem., 1, 134 (2003).CrossRefGoogle Scholar
  14. 14.
    O. S. Yel’tsov, V. S. Mokrushin, N. P. Belskaya, and N. M. Kozlova, Izv. Akad. Nauk, Ser. Khim., 440 (2003). [Russ. Chem. Bull., 52, 461 (2003).]CrossRefGoogle Scholar
  15. 15.
    A. Ane, G. Prestat, M. Thiam, S. Josse, M. Pipelier, J. P. Pradere, and D. Dubreuil, Nucleosides, Nucleotides Nucleic Acids, 21, 335 (2002).CrossRefGoogle Scholar
  16. 16.
    V. S. Berseneva, Yu. Yu. Morzherin, W. Dehaen, I. Luyten, and V. A. Bakulev, Tetrahedron, 57, 2179 (2001).CrossRefGoogle Scholar
  17. 17.
    V. S. Berseneva, A. V. Tkachev, Yu. Yu. Morzherin, W. Dehaen, I. Luyten, S. Toppet, and V. A. Bakulev, J. Chem. Soc., Perkin Trans. 1, 2133 (1998).Google Scholar
  18. 18.
    G. Giammona, M. Neri, B. Carlisi, A. Palazzo, and C. La Rosa, J. Heterocycl. Chem., 28, 325 (1991).CrossRefGoogle Scholar
  19. 19.
    L. I. Giannola, G. Giammona, S. Palazzo, and L. Lamartina, J. Chem. Soc., Perkin Trans. 1, 2707 (1984).Google Scholar
  20. 20.
    R. M. Acheson and J. D. Wallis, J. Chem. Soc., Perkin Trans. 1, 415 (1981).Google Scholar
  21. 21.
    U. Vogeli and W. Philipsborn, Helv. Chim. Acta, 61, 607 (1978).CrossRefGoogle Scholar
  22. 22.
    J. W. Lown and J. C. N. Ma, Can. J. Chem., 45, 939 (1967).CrossRefGoogle Scholar
  23. 23.
    S. Manzhos, H. Segawa, and K. Yamashita, Chem. Phys Lett., 527, 51 (2012).Google Scholar
  24. 24.
    V. A. Bren, A. D. Dubonosov, V. I. Minkin, A. V. Tsukanov, T. N. Gribanova, E. N. Shepelenko, Y. V. Revinsky, and V. P. Rybalkin, J. Phys. Org. Chem., 20, 917 (2007).Google Scholar
  25. 25.
    A. C. Tripathi, S. J. Gupta, G. N. Fatima, P. K. Sonar, A. Verma, and S. K. Saraf, Eur. J. Med. Chem., 72, 52 (2014).CrossRefGoogle Scholar
  26. 26.
    D. Kaminskyy, A. K. Gzella, and R. Lesyk, Synth. Commun., 44, 231 (2014).CrossRefGoogle Scholar
  27. 27.
    E. S. Darwish, I. A. Abdelhamid, M. A. Nasra, F. M. Abdel-Gallil, and D. H. Fleita, Helv. Chem. Acta, 93, 1204 (2010).CrossRefGoogle Scholar
  28. 28.
    N. Ghavtadze, R. Narayan, B. Wibbeling, and E.-U. Wurthwein, J. Org. Chem., 76, 5185 (2011).CrossRefGoogle Scholar
  29. 29.
    N. P. Belskaya, A. I. Bolgova, M. L. Kondrat’eva, O. S. Yel’tsov, and V. A. Bakulev, Izv. Akad. Nauk, Ser. Khim., 876 (2011). [Russ. Chem. Bull., 60, 896 (2011).]CrossRefGoogle Scholar
  30. 30.
    A. I. Mikhalev, S. V. Ukhov, and M. E. Konshin, Khim. Geterotsikl. Soedin., 629 (1994). [Chem. Heterocycl. Compd., 30, 551 (1994).]CrossRefGoogle Scholar
  31. 31.
    Y. Kobayashi, T. Nakatani, R. Tanaka, M. Okada, E. Torii, T. Harayama, and T. Kimachi, Tetrahedron, 67, 3457 (2011).CrossRefGoogle Scholar
  32. 32.
    A. S. Ivanov, N. Z. Tugusheva, L. M. Alekseeva, and V. G. Granik, Izv. Akad. Nauk, Ser. Khim., 837 (2004). [Russ. Chem. Bull., 53, 873 (2004).]CrossRefGoogle Scholar
  33. 33.
    M. P. Cava and M. I. Levinson, Tetrahedron, 41, 5061, (1985).CrossRefGoogle Scholar
  34. 34.
    Y. Vallee, P.-Y. Chavant, S. Pinet, N. Pelloux-Leon, R. Arnaud, and V. Barone, Phosphorus, Sulfur Silicon Relat. Elem., 120, 245 (1997).Google Scholar
  35. 35.
    A. S. Bell, C. W. G. Fishwick, and J. E. Reed, Tetrahedron, 54, 3219 (1998).CrossRefGoogle Scholar
  36. 36.
    I. T. Barnish, C. W. G. Fishwick, D. R. Hill, and C. Szantay, Jr., Tetrahedron Lett., 30, 4449 (1989).CrossRefGoogle Scholar
  37. 37.
    M. Iwaoka and N. Isozumi, Molecules, 17, 7266 (2012).CrossRefGoogle Scholar
  38. 38.
    V. I. Minkin and R. M. Minyaev, Chem. Rev., 101, 1247 (2001).CrossRefGoogle Scholar
  39. 39.
    Y. Nagao, T. Honjo, H. Iimori, S. Goto, S. Sano, M. Shiro, K. Yamaguchi, and Y. Sei, Tetrahedron Lett., 45, 8757 (2004).CrossRefGoogle Scholar
  40. 40.
    S. Scheiner, J. Chem. Phys., 134, 164313 (2011).Google Scholar
  41. 41.
    A. Pena-Hueso, F. Tellez; R. Vieto-Pena, R. O. Esquivel, A. Esparza-Ruiz, I. Ramos-Garcia, R. Contreras, N. Barba-Behrens, and A. Flores-Parra, J. Mol. Struct., 984, 409 (2010).CrossRefGoogle Scholar
  42. 42.
    A. I. Bolgova, K. I. Lugovik, J. O. Subbotina, P. A. Slepukhin, V. A. Bakulev, and N. P. Belskaya, Tetrahedron, 69, 7423 (2013).CrossRefGoogle Scholar

Copyright information

© Springer Science+Business Media New York 2014

Authors and Affiliations

  • N. P. Belskaya
    • 1
  • K. I. Lugovik
    • 1
  • A. D. Ivina
    • 1
  • V. A. Bakulev
    • 1
  • Z. J. Fan
    • 2
  1. 1.Ural Federal University named after the First President of Russia B. N. YeltsinYekaterinburgRussia
  2. 2.State Key Laboratory of Elemento-organic ChemistryNankai UniversityTianjinP. R. China

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