Skip to main content
SpringerLink
Log in

Unsaturated germanes and stannanes in the synthesis of nitrogen-containing heterocycles by [2+3]-cycloaddition

  • Published:
Chemistry of Heterocyclic Compounds Aims and scope

Abstract

Literature data and the results of fundamental investigations on synthetic methods and chemical reactions of the products of 1,3-dipolar additions to unsaturated germanes and stannanes are reviewed.

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. E. Lukevits and V. V. Dirneis, Latv. Khim. Zh., No. 2, 131 (1992).

    Google Scholar 

  2. E. Lukevits and V. V. Dirneis, Latv. Khim. Zh. No. 3, 282 (1992).

    Google Scholar 

  3. G. Guillerm and M. LeQuan, Compt. Rend.,269, 853 (1969).

    Google Scholar 

  4. L. G. Sharanina, V. S. Zavgorodnyi, and A. A. Petrov, Zh. Org. Khim.,38, 1146 (1967).

    Google Scholar 

  5. G. Guillerm, A. L'Honore, L. Veniard, G. Pourcelot, and J. Benaim, Bull. Soc. Chim. France, 2739 (1973).

  6. R. Huisgen, H. Gotthardt, and R. Garshey, Chem. Ber.,101, 536 (1968).

    Google Scholar 

  7. T. Sakamoto, F. Shiga, D. Uchiyama, Y. Kondo, and H. Yamanaka, Heterocycles,33, 813 (1992).

    Google Scholar 

  8. M. A. Khan, B. M. Lynch, and Y.-Y. Hung, Can. J. Chem.,41, 1540 (1963).

    Google Scholar 

  9. A. S. Kostyuk, K. A. Knyaz'kov, S. V. Ponomarev, and I. F. Lutsenko, Zh. Org. Khim.,55, 2088 (1985).

    Google Scholar 

  10. M. M. Demina, A. S. Medvedeva, N. I. Prochuk, I. D. Kalikhman, and N. S. Vyazankin, Zh. Org. Khim.,49, 1331 (1979).

    Google Scholar 

  11. M. M. Demina, A. S. Medvedeva, N. I. Prochuk, I. D. Kalikhman, É. I. Brodskaya, G. A. Kalabin, and N. S. Vyazankin, Zh. Org. Khim.,51, 1324 (1981).

    Google Scholar 

  12. A. S. Medvedeva, M. M. Demina, A. I. Borisova, I. D. Kalikhman, and N. S. Vyazankin, Zh. Org. Khim.,50, 1775 (1980).

    Google Scholar 

  13. A. S. Medvedeva, M. M. Demina, A. I. Borisova, I. D. Kalikhman, and N. S. Vyazankin, J. Organomet. Chem.,231, 109 (1982).

    Article  Google Scholar 

  14. O. A. Kruglaya, I. B. Fedot'eva, B. V. Fedot'ev, I. D. Kalikhman, and N. S. Vyazankin, Zh. Org. Khim.,48, 1431 (1978).

    Google Scholar 

  15. M. M. Demina, A. S. Medvedeva, N. I. Prochuk, I. D. Kalikhman, É. I. Brodskaya, G. A. Kalabin, and N. S. Vyazankin, Zh. Org. Khim.,51, 366 (1981).

    Google Scholar 

  16. Yu. L. Piterskaya, A. V. Khramchikhim, and M. D. Stadnichuk, Zh. Org. Khim.,66, 1188 (1996).

    Google Scholar 

  17. G. Himbert, D. Frank, and M. Regitz, Chem. Ber.,109, 370 (1976).

    Google Scholar 

  18. G. Himbert and M. Regitz, Synthesis, 571 (1972).

  19. G. Himbert and M. Regitz, Chem. Ber.,105, 2963 (1972).

    Google Scholar 

  20. G. Himbert and M. Regitz, Chem. Ber.,107, 2513 (1974).

    Google Scholar 

  21. G. Himbert and M. Regitz, Lieb. Ann. Chem., 1505 (1973).

  22. A. Padwa and J. G. Macdonald, Tetrahedron Lett.,23, 3219 (1982).

    Article  Google Scholar 

  23. A. Padwa and J. G. Macdonald, J. Org. Chem.,48, 3189 (1983).

    Article  Google Scholar 

  24. E. Lukevics, V. Dirnens, P. Arsenyan, J. Popelis, and A. Kemme, Main Group Met. Chem.,19, 167 (1996).

    Google Scholar 

  25. E. Lukevics, M. Veveris, and V. Dirnens, Appl. Organomet. Chem.,11, 805 (1997).

    Article  Google Scholar 

  26. E. Lukevics, V. Dirnens, N. Pokrovska, J. Popelis, and A. Kemme, Main Group Met. Chem.,18, 337 (1995).

    Google Scholar 

  27. E. Lukevics, P. Arsenyan, S. Belyakov, and J. Popelis, J. Organomet. Chem.,558, 155 (1998).

    Article  Google Scholar 

  28. E. Lukevits and P. Arsenyan, Khim. Geterotsikl. Khim., No. 4, 564 (1998).

    Google Scholar 

  29. E. Lukevits, P. Arsenyan, S. Belyakov, and J. Popelis, Main Group Met. Chem.,21, 557 (1998).

    Google Scholar 

  30. E. Lukevics, P. Arsenyan, and M. Veveris, Metal-Based Drugs,5, 251 (1998).

    Google Scholar 

  31. N. Almiarante and L. Forti, J. Heterocycl. Chem.,21, 1121 (1984).

    Google Scholar 

  32. D. A. Lefkaditis, N. G. Arguropoulous and D. N. Nicolaides, Liebig. Ann. Chem, 1863 (1986).

  33. O. Tsuge, S. Kanemasa and S. Tanenka, Bull. Chem. Soc. Jpn.,59, 3631 (1986).

    Google Scholar 

  34. P. Caramella, T. Bandiera, P. Crunanger and F. M. Albini Tetrahedron,40, 441 (1984).

    Article  Google Scholar 

  35. E. M. Xenikaki and E. C. Argyropoulou, Tetrahedron Lett.,26, 4105 (1985).

    Article  Google Scholar 

  36. M. Nitta and N. Kanomata, Chem. Lett., 1925 (1986).

  37. M. Soufiaoui, B. Syassi, B. Daou, and N. Baba, Tetrahed. Lett.,32, 3699 (1991).

    Google Scholar 

  38. E. C. Argyropolou, and E. Thessalonikeos, J. Heterocycl. Chem.,28, 1088 (1991).

    Google Scholar 

  39. W. Fliege, R. Grashey, and R. Huisgen, Chem. Ber.,117, 1194 (1984).

    Google Scholar 

  40. E. Lukevics, V. Dirnens, J. Popelis, and A. Kemme, J. Organomet. Chem.,521, 235 (1996).

    Article  Google Scholar 

  41. T. Mukaiyama and T. Hoshito, J. Am. Chem. Soc.,82, 5339 (1960).

    Article  Google Scholar 

  42. Y. Kondo, D. Uchiyama, T. Sakamoto, and H. Yamanaka, Tetrahedron Lett.,30, 4249 (1989).

    Article  Google Scholar 

  43. T. Sakamoto, Y. Kondo, D. Uchiyama, and H. Yamanaka, Tetrahedron,47, 5111 (1991).

    Article  Google Scholar 

  44. T. Sakamoto, F. Shiga D. Uchiyama, and H. Yamanaka, Heterocycles,33, 813 (1992).

    Google Scholar 

  45. T. Sakamoto, D. Uchimaya, Y. Kondo, and H. Yamanaka, Heterocycles,35, 1273 (1993).

    Google Scholar 

  46. T. Sakamoto, D. Uchimaya, Y. Kondo, and H. Yamanaka, Chem. Phar. Bull.,41, 478 (1993).

    Google Scholar 

  47. D. Ichiyama, M. Yabe, H. Kameyama, T. Sakamoto, Y. Kondo, and H. Yamanaka, Heterocycles,43, 1301 (1996).

    Google Scholar 

Download references

Authors
  1. E. Lukevits
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. P. Arsenyan
    View author publications

    You can also search for this author in PubMed Google Scholar

Additional information

Dedicated to Professor A. Katritzky on his seventieth birthday.

Latvian Institute of Organic Synthesis, Riga LV-1006. Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 9, pp. 1155–1169, September, 1998.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Lukevits, E., Arsenyan, P. Unsaturated germanes and stannanes in the synthesis of nitrogen-containing heterocycles by [2+3]-cycloaddition. Chem Heterocycl Compd 34, 989–1000 (1998). https://doi.org/10.1007/BF02251542

Download citation

  • Received:

  • Issue Date:

  • DOI: https://doi.org/10.1007/BF02251542

Keywords

Search

Navigation