Skip to main content
SpringerLink
Log in

Alkylation of pyridinecarbaldehyde oximes with epoxy compounds

  • Published:
Russian Journal of Organic Chemistry Aims and scope Submit manuscript

Abstract

O-and N-Alkylation products were obtained by reactions of pyridine-2-,-3-, and-4-carbaldehyde oximes with enantiomerically pure and racemic epoxy compounds (1,2-epoxypropane, 1-phenyl-1,2-epoxyethane, 1-chloro-2,3-epoxypropane, and 1-bromo-2,3-epoxypropane) in the presence of bases and under conditions of phase-transfer catalysis. A series of new amino alcohols was synthesized by condensation of amines with products of O-alkylation of pyridinecarbaldehyde oximes with 1-halo-2,3-epoxypropanes.

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. Markova, Y.W., Chem. Pharm. J., 1969, vol. 3, p. 13.

    CAS  Google Scholar 

  2. Wolfgang, K., Justus Justus Liebigs Ann. Chem., 1970, vol. 733, p. 192.

    Google Scholar 

  3. Güler, E., Şen, N., Sırıt, A., Kurbanov, S., and MirzaoǦlu, R., Org. Prep. Proced. Int., 1998, vol. 30, p. 195.

    Article  Google Scholar 

  4. Kurbanov, S., Sırıt, A., and Şen, N., Org. Prep. Proced. Int., 1999, vol. 31, p. 681.

    CAS  Google Scholar 

  5. Kurbanlı, S., Şen, N., Güler, E., and Koçak, A., Synth. Commun., 2004, vol. 34, p. 1663.

    Article  CAS  Google Scholar 

  6. Gawley, R.E. and Nagy, T., Tetrahedron Lett., 1984, vol. 25, p. 263.

    Article  CAS  Google Scholar 

  7. Yasuo, K., Ryoko, O., and Yasuhisa, A., Arch. Microbiol., 1998, vol. 170, p. 85.

    Article  Google Scholar 

  8. Zhou, J.F., Tu-Shu, J., and Feng, J.C., Synth. Commun., 2002, vol. 32, p. 959.

    Article  CAS  Google Scholar 

  9. Varkar, P., Rathore, R., and Chandrase-Karan, S., J. Org. Chem., 1986, vol. 51, p. 3063.

    Article  Google Scholar 

  10. Curran, D.P., Brill, J.F., and Rakiewicz, D.M., J. Org. Chem., 1984, vol. 49, p. 1654.

    Article  CAS  Google Scholar 

  11. Hidlicky, M., Reduction in Organic Chemistry, Chichester: Ellis Horwood, 1984, p. 132.

    Google Scholar 

  12. Cohen, J.H., Abdel-Magid, A.F., Almond, H.R., and Maryanoff, C.A., Tetrahedron Lett., 2002, vol. 43, p. 1977.

    Article  CAS  Google Scholar 

  13. Norman, A.L. and Balasubramanian, N., Tetrahedron Lett., 1985, vol. 26, p. 4331.

    Article  Google Scholar 

  14. Ghiaci, M. and Bakhtiari, K., Synth. Commun., 2001, vol. 31, p. 1803.

    Article  CAS  Google Scholar 

  15. Hekmatshoar, R., Heravi, M.M., Beheshtiha, Y.S., and Asadolah, K., Monatsh. Chem., 2002, vol. 133, p. 111.

    Article  CAS  Google Scholar 

  16. Iranpoor, N., Firouzabadi, H., and Aghapour, G., Synth. Commun., 2002, vol. 32, p. 2535.

    Article  CAS  Google Scholar 

  17. Mitcher, L.A., The Organic Chemistry of Drug Synthesis, New York: Wiley, 1980, vol. 2.

    Google Scholar 

  18. Desideri, N., Sestili, I., Manarini, S., Cerletti, C., and Stein, M.L., Eur. J. Med. Chem., 1991, vol. 26, p. 455.

    Article  CAS  Google Scholar 

  19. Steven, A.R. and Richard, J.K.T., Tetrahedron Lett., 2000, vol. 41, p. 10357.

    Article  Google Scholar 

  20. Leclerc, G., Mann, A., and Wermuth, C.G., J. Med. Chem., 1977, vol. 20, p. 1657.

    Article  CAS  Google Scholar 

  21. Manna, F., Bolasco, A., Bizzari, B., and Lena, R., Farmaco, 1996, vol. 51, p. 579.

    CAS  Google Scholar 

  22. Arena, F., Manna, F., Pizza, C., Stein, M.L., and Grifantini, M., J. Med. Chem., 1975, vol. 18, p. 1147.

    Article  CAS  Google Scholar 

  23. Kurbanova, R.A., MirzaoǦlu, R., Kurbanov, S., Karataş, İ., Pamuk, V., Ozcan, E., Okudan, A., and Guler, E., J. Adhesion Sci. Technol., 1997, vol. 11, p. 105.

    CAS  Google Scholar 

  24. Kleinspehn, G.G., Jung, J.A., and Studniarz, S.A., J. Org. Chem., 1967, vol. 32, p. 460.

    Article  CAS  Google Scholar 

  25. Ginsburg, S. and Wilson, I.B., J. Am. Chem. Soc., 1957, vol. 79, p. 481.

    Article  CAS  Google Scholar 

  26. Brown, D.S., Gallogher, P.T., Lightfoot, A.P., Moody, C.J., Slwin, A.M.Z., and Swann, E., Tetrahedron, 1995, vol. 51, p. 11473.

    Article  CAS  Google Scholar 

  27. Cativiela, C., D. Diaz-de-Villegas, M., and Glavez, J.A., Tetrahedron: Asymmetry, 1996, vol. 7, p. 529.

    Article  CAS  Google Scholar 

  28. McClure, D.E., Arison, B.H., and Baldwin, J.J., J. Am. Chem. Soc., 1979, vol. 101, p. 3666.

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Department of Chemistry, University of Selcuk, 42031, Konya, Turkey

    N. Şen & S. Kurbanov

  2. Department of Chemical Engineering, University of Selcuk, 42031, Konya, Turkey

    Y. Kar

Authors
  1. N. Şen
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Y. Kar
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. S. Kurbanov
    View author publications

    You can also search for this author in PubMed Google Scholar

Additional information

Published in Russian in Zhurnal Organicheskoi Khimii, 2007, Vol. 43, No. 3, pp. 450–454.

The text was submitted by the authors in English.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Şen, N., Kar, Y. & Kurbanov, S. Alkylation of pyridinecarbaldehyde oximes with epoxy compounds. Russ J Org Chem 43, 449–453 (2007). https://doi.org/10.1134/S1070428007030220

Download citation

  • Received:

  • Issue Date:

  • DOI: https://doi.org/10.1134/S1070428007030220

Keywords

Search

Navigation