Skip to main content
SpringerLink
Log in

Interaction of heteroatom-containing propynals with S-, N-binucleophiles

  • Published:
Chemistry of Heterocyclic Compounds Aims and scope

Abstract

Reactions of α-silicon-and α-germanium-containing acetylenic aldehydes with 2-aminoethanethiol, ethylenediamine, and 2-amino-1,2,4-triazole proceed chemoselectively at the aldehyde group. The ratio of tautomers, azomethine and 1,3-thiazolidine, on interaction with 2-aminoethanethiol depends significantly on the nature of the heteroatom at the triple bond of the aldehyde, the presence of a catalyst, and the use of microwave activation.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Similar content being viewed by others

References

  1. A. S. Medvedeva, Zh. Org. Khim., 32, 289 (1996).

    CAS  Google Scholar 

  2. A. S. Medvedeva, A. I. Borisova, and N. G. Voronkov, Metalloorg. Khim., 2, 1229 (1989).

    CAS  Google Scholar 

  3. A. S. Medvedeva, A. V. Mareev, A. V. Afonin, and I. A. Ushakov, Zh. Org. Khim., 41, 478 (2005).

    Google Scholar 

  4. A. S. Medvedeva, A. V. Khatashkeev, A. V. Mareev, A. V. Afonin, and I. A. Ushakov, Zh. Org. Khim., 41, 1740 (2005).

    Google Scholar 

  5. A. Ino, Y. Hasegawa, and A. Murabayashi, Tetrahedron, 55, 10283 (1999).

  6. A. Ino and A. Murabayashi, Tetrahedron, 55, 10271 (1999).

  7. A. Ino and A. Murabayashi, Tetrahedron, 57, 1897 (2001).

    Article  CAS  Google Scholar 

  8. A. Zamri and M. A. Abdallah, Tetrahedron, 56, 249 (2000).

    Article  CAS  Google Scholar 

  9. B. H. Wilmore, P. B. Cassidy, R. L. Warters, and J. C. Roberts, J. Med. Chem., 44, 2661 (2001).

    Article  CAS  Google Scholar 

  10. J. C. Roberts, H. T. Nagasawa, R. T. Zera, R. F. Fricke, and D. J. W. Goon, J. Med. Chem., 30, 1891 (1987).

    Article  CAS  Google Scholar 

  11. H. T. Nagasawa, D. J. W. Goon, W. P. Muldoon, and R. T. Zera, J. Med. Chem., 27, 591 (1984).

    Article  CAS  Google Scholar 

  12. H. T. Nagasawa, D. J. W. Goon, R. T. Zera, and D. L. Yuzon, J. Med. Chem., 25, 489 (1982).

    Article  CAS  Google Scholar 

  13. L. Szilagyi and Z. Gyorgydeak, J. Am. Chem. Soc., 101, 427 (1979).

    Article  CAS  Google Scholar 

  14. V. V. Alekseev and K. N. Zelenin, Khim. Geterotsikl. Soedin., 1068 (1998). [Chem. Heterocycl. Comp., 34, 919 (1999)].

    Google Scholar 

  15. R. G. Kallen, J. Am. Chem. Soc., 93, 6236 (1971).

    Article  CAS  Google Scholar 

  16. N. A. Keiko, E. A. Funtikova, L. G. Stepanova, Yu. A. Chuvashev, L. I. Larina, and M. G. Voronkov, J. Sulfur Chem., 25, 351 (2004).

    CAS  Google Scholar 

  17. I. Iovel’, L. Golomba, Yu. Popelis, S. Grinberga, S. Belyakov, and E. Lukevics, Khim. Geterotsikl. Soedin., 1375 (2002). [Chem. Heterocycl. Comp., 38, 1270 (2002)].

    Google Scholar 

  18. A. S. Medvedeva, A. V. Mareev, A. I. Borisova, and A. V. Afonin, Arkivoc, 13, 157 (2003).

    Google Scholar 

  19. A. V. Mareev, A. S. Medvedeva, A. V. Khatashkeev, and A. V. Afonin, Mendeleev. Commun., 263 (2005).

  20. R. N. Gedye, F. Smith, K. Westaway, H. Ali, L. Baldisera, L. Laberge, and J. Roussel, Tetrahedron Lett., 27, 279 (1986).

    Article  CAS  Google Scholar 

  21. A. Loupy, A. Petit, J. Hamelin, F. Texier-Boullet, P. Jacquault, and D. Mathe, Synthesis, 1213 (1998).

  22. R. S. Varma, Green Chem., 1, 43 (1999).

    Article  CAS  Google Scholar 

  23. F. Louërat, K. Bougrin, A. Loupy, A. M. O. Retana, J. Pagalday, and F. Palacios, Heterocycles, 48, 161 (1998).

    Article  Google Scholar 

  24. S. E. Sen, S. M. Smith and K. A. Sillivan, Tetrahedron, 55, 12657 (1999).

    Google Scholar 

  25. P. A. Vigato and S. Tamburini, Coord. Chem. Rev., 248, 1717 (2004).

    Article  CAS  Google Scholar 

  26. A. Simion, C. Simion, T. Kanda, S. Nagashima, Y. Mitoma, T. Yamada, K. Mimura, and M. Tashiro, J. Chem. Soc., Perkin Trans. 1, 2071 (2001).

  27. M. M. Demina, A. S. Medvedeva, N. I. Protsuk, and N. S. Vyazankin, Zh. Obshch. Khim., 48, 1563 (1978).

    CAS  Google Scholar 

  28. A. S. Medvedeva, M. M. Demina, and N. S. Vyazankin, Izv. Akad. Nauk SSSR, Ser. Khim., 967 (1977).

Download references

Author information

Authors and Affiliations

  1. Irkutsk A. E. Favorsky Institute of Chemistry, Siberian Branch of the Russian Academy of Sciences, Irkutsk, 664033

    M. M. Demina, P. S. Novopashin, T. V. Kon’kova, G. I. Sarapulova, A. V. Afonin & A. S. Medvedeva

Authors
  1. M. M. Demina
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. P. S. Novopashin
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. T. V. Kon’kova
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. G. I. Sarapulova
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. A. V. Afonin
    View author publications

    You can also search for this author in PubMed Google Scholar

  6. A. S. Medvedeva
    View author publications

    You can also search for this author in PubMed Google Scholar

Additional information

Dedicated to our teacher, Academician of the Russian Academy of Sciences M. G. Voronkov, in connection with his 85th birthday

__________

Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 11, pp. 1697–1704, November, 2006.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Demina, M.M., Novopashin, P.S., Kon’kova, T.V. et al. Interaction of heteroatom-containing propynals with S-, N-binucleophiles. Chem Heterocycl Compd 42, 1457–1463 (2006). https://doi.org/10.1007/s10593-006-0262-4

Download citation

  • Received:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s10593-006-0262-4

Keywords

Search

Navigation