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.
Similar content being viewed by others
References
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).
I. Coldham and R. Hufton, Chem. Rev., 105, 2765 (2005).
J. W. Lown, in: A. Padwa (editor), 1,3-Dipolar Cycloaddition Chemistry, Vol. 1, Wiley, New York (1984), p. 653.
J. S. Clark (editor), Nitrogen, Oxygen and Sulfur Ylide Chemistry, Oxford University Press, Oxford (2002).
A. K. Yudin (editor), Aziridines and Epoxides in Organic Synthesis, Wiley-VCH, Weinheim (2006).
H. W. Heine and R. Peavy, Tetrahedron Lett., 6, 3123 (1965).
H. W. Heine, A. B. Smith, III, and J. D. Bower, J. Org. Chem., 33, 1097 (1968).
D. M. B. Hickey, C. J. Moody, and C. W. Rees, J. Chem. Soc., Perkin Trans. 1, 1119 (1986).
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).
E. Ullman and W. A. Henderson, Jr., J. Am. Chem. Soc., 86, 5050 (1964).
T. DoMinh and A. M. Trozzolo, J. Am. Chem. Soc., 94, 4046 (1972).
H. W. Heine and R. P. Henzel, J. Org. Chem,. 34, 171 (1969).
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).
A. Padwa and L. Gehrlein, J. Am. Chem. Soc., 94, 4933 (1972).
A. F. Khlebnikov, M. S. Novikov, P. P. Petrovskii, J. Magull, and A. Ringe, Org. Lett., 11, 979 (2009).
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).
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).
K. Matsumoto, Y. Ikemi, C. Takayama, K. Aoyama, and T. Uchida, Chem. Lett., 1647 (1990).
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).]
K. Matsumoto and K. Maruyama, Chem. Lett., 759 (1973).
O. Meth-Cohn, N. J. R. Williams, A. MacKinnon, and J. A. K. Howard, Tetrahedron, 54, 9837 (1998).
A. F. Khlebnikov, M. S. Novikov, P. P. Petrovskii, and H. Stoeckli-Evans, J. Org. Chem., 76, 5384 (2011).
T. Hudlicky, J. O. Frazier, G. Seoane, M. Tiedje, A. Seoane, L. D. Kwart, and C. Beal, J. Am. Chem. Soc., 108, 3755 (1986).
T. Hudlicky, G. Seoane, and T. C. Lovelace, J. Org. Chem., 53, 2094 (1988).
T. Hudlicky, H. Luna, J. D. Price, and F. Rulin, J. Org. Chem., 55, 4683 (1990).
W. Friebolin and W. Eberbach, Tetrahedron, 57, 4349 (2001).
A. G. Schultz, R. R. Staib, and K. K. Eng, J. Org. Chem., 52, 2968 (1987).
J. W. Lown and K. Matsumoto, J. Chem. Soc., Chem. Commun., 692 (1970).
J. W. Lown and K. Matsumoto, J. Org. Chem., 36, 1405 (1971).
K. Ishii, M. Kido, M. Noji, and S. Sugiyama, Org. Biomol. Chem., 6, 3186 (2008).
A. C. Oehlschlager, A. S. Yim, and M. H. Akhtar, Can. J. Chem., 56, 273 (1978).
O. Tsuge, K. Oe, and N. Kawaguchi, Chem. Lett, 1585 (1981).
R. Huisgen and H. Mader, Angew. Chem., Int. Ed, 8, 604 (1969).
S. Oida and E. Ohki, Chem. Pharm. Bull, 17, 2461 (1969).
M. A. Kuznetsov, A. V. Ushkov, S. I. Selivanov, and L. M. Kuznetsova, Khim. Geterotsikl. Soedin., 1320 (2006). [Chem. Heterocycl. Compd., 42, 1143 (2006)].
P. Garner, K. Sunitha, and T. Shanthilal, Tetrahedron Lett., 29, 3525 (1988).
P. Garner, K. Sunitha, W.-B. Ho, W. J. Youngs, V. O. Kennedy, and A. Djebli, J. Org. Chem., 54, 2041 (1989).
P. P. Garner, P. B. Cox, S. J. Klippenstein, W. J. Youngs, and D. B. McConville, J. Org. Chem., 59, 6510 (1994).
P. Garner, P. B. Cox, J. T. Anderson, J. Protasiewicz, and R. Zaniewski, J. Org. Chem., 62, 493 (1997).
P. Garner, W. B. Ho, S. K. Grandhee, W. J. Youngs, and V. O. Kennedy, J. Org. Chem., 56, 5893 (1991).
Author information
Authors and Affiliations
Corresponding author
Additional information
Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 1, pp. 187-198, January, 2012.
Rights 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
Received:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s10593-012-0981-7