Skip to main content
Log in

Fused aziridines as sources of azomethine ylides

  • Published:
Chemistry of Heterocyclic Compounds Aims and scope

The use of fused aziridines as sources of azomethine ylides in the synthesis of polyheterocyclic compounds is examined. Features of thermo- and photolytic opening of aziridines and aspects of the stereo-, regio-, and chemoselectivity of cycloaddition and electrocyclization of azomethine ylides are discussed.

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

Access this article

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

Instant access to the full article PDF.

Similar content being viewed by others

References

  1. A. Padwa and W. H. Pearson (editors), Synthetic Applications of 1,3-Dipolar Cycloaddition Chemistry toward Heterocycles and Natural Products, John Wiley and Sons, New York (2002).

    Google Scholar 

  2. I. Coldham and R. Hufton, Chem. Rev., 105, 2765 (2005).

    Article  CAS  Google Scholar 

  3. J. W. Lown, in: A. Padwa (editor), 1,3-Dipolar Cycloaddition Chemistry, Vol. 1, Wiley, New York (1984), p. 653.

    Google Scholar 

  4. J. S. Clark (editor), Nitrogen, Oxygen and Sulfur Ylide Chemistry, Oxford University Press, Oxford (2002).

    Google Scholar 

  5. A. K. Yudin (editor), Aziridines and Epoxides in Organic Synthesis, Wiley-VCH, Weinheim (2006).

    Google Scholar 

  6. H. W. Heine and R. Peavy, Tetrahedron Lett., 6, 3123 (1965).

    Article  Google Scholar 

  7. H. W. Heine, A. B. Smith, III, and J. D. Bower, J. Org. Chem., 33, 1097 (1968).

    Article  CAS  Google Scholar 

  8. D. M. B. Hickey, C. J. Moody, and C. W. Rees, J. Chem. Soc., Perkin Trans. 1, 1119 (1986).

  9. H. W. Heine, T. A. Newton, G. J. Blosick, K. C. Irving, C. Meyer, and G. B. Corcoran, III, J. Org. Chem., 38, 651 (1973).

    Article  CAS  Google Scholar 

  10. E. Ullman and W. A. Henderson, Jr., J. Am. Chem. Soc., 86, 5050 (1964).

    Article  CAS  Google Scholar 

  11. T. DoMinh and A. M. Trozzolo, J. Am. Chem. Soc., 94, 4046 (1972).

    Article  Google Scholar 

  12. H. W. Heine and R. P. Henzel, J. Org. Chem,. 34, 171 (1969).

    Article  CAS  Google Scholar 

  13. A. I. Zbruyev, F. G. Yaremenko, V. A. Chebanov, S. M. Desenko, O. V. Shishkin, E. V. Lukinova, and I. V. Knyazeva, Russ. Chem. Bull., 55, 362 (2006).

    Article  CAS  Google Scholar 

  14. A. Padwa and L. Gehrlein, J. Am. Chem. Soc., 94, 4933 (1972).

    Article  CAS  Google Scholar 

  15. A. F. Khlebnikov, M. S. Novikov, P. P. Petrovskii, J. Magull, and A. Ringe, Org. Lett., 11, 979 (2009).

    Article  CAS  Google Scholar 

  16. A. F. Khlebnikov, M. S. Novikov, M. V. Golovkina, P. P. Petrovskii, A. S. Konev, D. S. Yufit, and H. Stoeckli-Evans, Org. Biomol. Chem., 9 , 3886 (2011).

    Article  CAS  Google Scholar 

  17. A. F. Khlebnikov, M. S. Novikov, P. P. Petrovskii, A. S. Konev, D. S. Yufit, S. I. Selivanov, and H. Frauendorf, J. Org. Chem., 75, 5211 (2010).

    Article  CAS  Google Scholar 

  18. K. Matsumoto, Y. Ikemi, C. Takayama, K. Aoyama, and T. Uchida, Chem. Lett., 1647 (1990).

  19. M. S. Novikov, A. F. Khlebnikov, M. A. Egarmin, Yu. Kopf, and R. R. Kostikov, Zh. Org. Khim., 40, 1542 (2004). [Russ. J. Org. Chem., 40, 1493 (2004).]

    Google Scholar 

  20. K. Matsumoto and K. Maruyama, Chem. Lett., 759 (1973).

  21. O. Meth-Cohn, N. J. R. Williams, A. MacKinnon, and J. A. K. Howard, Tetrahedron, 54, 9837 (1998).

    Article  CAS  Google Scholar 

  22. A. F. Khlebnikov, M. S. Novikov, P. P. Petrovskii, and H. Stoeckli-Evans, J. Org. Chem., 76, 5384 (2011).

    Article  CAS  Google Scholar 

  23. T. Hudlicky, J. O. Frazier, G. Seoane, M. Tiedje, A. Seoane, L. D. Kwart, and C. Beal, J. Am. Chem. Soc., 108, 3755 (1986).

    Article  CAS  Google Scholar 

  24. T. Hudlicky, G. Seoane, and T. C. Lovelace, J. Org. Chem., 53, 2094 (1988).

    Article  CAS  Google Scholar 

  25. T. Hudlicky, H. Luna, J. D. Price, and F. Rulin, J. Org. Chem., 55, 4683 (1990).

    Article  CAS  Google Scholar 

  26. W. Friebolin and W. Eberbach, Tetrahedron, 57, 4349 (2001).

    Article  CAS  Google Scholar 

  27. A. G. Schultz, R. R. Staib, and K. K. Eng, J. Org. Chem., 52, 2968 (1987).

    Article  CAS  Google Scholar 

  28. J. W. Lown and K. Matsumoto, J. Chem. Soc., Chem. Commun., 692 (1970).

  29. J. W. Lown and K. Matsumoto, J. Org. Chem., 36, 1405 (1971).

    Article  CAS  Google Scholar 

  30. K. Ishii, M. Kido, M. Noji, and S. Sugiyama, Org. Biomol. Chem., 6, 3186 (2008).

    Article  CAS  Google Scholar 

  31. A. C. Oehlschlager, A. S. Yim, and M. H. Akhtar, Can. J. Chem., 56, 273 (1978).

    Article  CAS  Google Scholar 

  32. O. Tsuge, K. Oe, and N. Kawaguchi, Chem. Lett, 1585 (1981).

  33. R. Huisgen and H. Mader, Angew. Chem., Int. Ed, 8, 604 (1969).

    Google Scholar 

  34. S. Oida and E. Ohki, Chem. Pharm. Bull, 17, 2461 (1969).

    Article  CAS  Google Scholar 

  35. M. A. Kuznetsov, A. V. Ushkov, S. I. Selivanov, and L. M. Kuznetsova, Khim. Geterotsikl. Soedin., 1320 (2006). [Chem. Heterocycl. Compd., 42, 1143 (2006)].

    Google Scholar 

  36. P. Garner, K. Sunitha, and T. Shanthilal, Tetrahedron Lett., 29, 3525 (1988).

    Article  CAS  Google Scholar 

  37. P. Garner, K. Sunitha, W.-B. Ho, W. J. Youngs, V. O. Kennedy, and A. Djebli, J. Org. Chem., 54, 2041 (1989).

    Article  CAS  Google Scholar 

  38. P. P. Garner, P. B. Cox, S. J. Klippenstein, W. J. Youngs, and D. B. McConville, J. Org. Chem., 59, 6510 (1994).

    Article  CAS  Google Scholar 

  39. P. Garner, P. B. Cox, J. T. Anderson, J. Protasiewicz, and R. Zaniewski, J. Org. Chem., 62, 493 (1997).

    Article  CAS  Google Scholar 

  40. P. Garner, W. B. Ho, S. K. Grandhee, W. J. Youngs, and V. O. Kennedy, J. Org. Chem., 56, 5893 (1991).

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to A. F. Khlebnikov.

Additional information

Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 1, pp. 187-198, January, 2012.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Khlebnikov, A.F., Novikov, M.S. Fused aziridines as sources of azomethine ylides. Chem Heterocycl Comp 48, 179–190 (2012). https://doi.org/10.1007/s10593-012-0981-7

Download citation

  • Received:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s10593-012-0981-7

Keywords

Navigation