Skip to main content
SpringerLink
Log in

Synthesis of functionally substituted isoxazole-containing benzaldehydes of the vanillin series and Schiff bases derived therefrom

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

Abstract

5-Chloromethyl-3-methyl-1,2-oxazole reacted with benzaldehydes of the vanillin series in the presence of potassium carbonate in boiling ethanol (Williamson reaction) to produce the corresponding isoxazolylmethyloxy-substituted benzaldehydes which were brought into condensation with aromatic amines and diamines in boiling methanol to obtain functionally substituted Schiff bases.

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. Lemke, T.L., Review of Organic Functional Groups: Introduction to Medicinal Organic Chemistry, Philadelphia: Wolters Kluwer/Lippincott Williams & Wilkins Health, 2012, 5th ed.; Wilson and Gisvold’s Textbook of Organic Medicinal and Pharmaceutical Chemistry, Beale, J.M., Jr. and Block, J.H., Eds., Baltimore: Lippincott Williams & Wilkins, 2011, 12th ed.; Analogue-Based Drug Discovery, Fischer, J. and Ganellin, C.R., Eds., Weinheim: Wiley-VCH, 2006; Corey, E.J., Czakó, B., and Kürti, L., Molecules and Medicine, Hoboken NJ: Wiley, 2007; Kleemann, A., Engel, J., Kutscher, B., and Reichert, D., Pharmaceutical Substances: Syntheses, Patents, Applications, Stuttgart: Georg Thieme, 2001, 4th ed.; Silverman, R., The Organic Chemistry of Drug Design and Drug Action, Amsterdam: Elsevier, 2004, 2nd ed.

    Google Scholar 

  2. Kletskov, A.V., Potkin, V.I., Petkevich, S.K., Dikusar, E.A., Bumagin, N.A., Veselov, I.S., Denisov, A.A., Pashkevich, S.G., Zolotar’, R.M., and Chepik, O.P., Abstracts of Papers, IV Mezhdunarodnaya nauchnaya konferentsiya, posvyashchennaya 100-letiyu so dnya rozhdeniya akademika A.A. Akhrema: Khimiya, struktura i funktsii biomolekul (IVth Int. Scientific Conf. Dedicated to the 100th Anniversary of Academician A.A. Akhrem: Chemistry, Structure, and Functions of Biomolecules), Minsk, Oct 17–19, 2012, p. 178; Dikusar, E.A., Potkin, V.I., Zhukovskaya, N.A., Petkevich, S.K., Zvereva, T.D., and Rudakov, D.A., Materiali za 8-a mezhdunarodna nauchna praktichna knf. “Nastoyashchi izsledovaniya i razvitie.” Khimiya i khimicheski tekhnologii (Proc. 8th Int. Scientific and Practical Conf. “Modern Science and Development.” Chemistry and Chemical Technologies), Sofia, Bulgaria, Jan 17-25, 2012, p. 33; Potkin, V., Zubenko, Yu., Bykhovetz, A., Zolotar, R., and Goncharuk, V., Nat. Prod. Commun., 2009, vol. 4, p. 1205.

    Google Scholar 

  3. Gadzhily, R.A. and Aliev, A.A., Russ. J. Org. Chem., 2002, vol. 38, p. 415; Gadzhily, R.A., Potkin, V.I., Aliev, A.G., Gadzhieva, L.Ya., Petkevich, S.K., and Dikusar, E.A., Russ. J. Org. Chem., 2011, vol. 47, p. 1531.

    Article  CAS  Google Scholar 

  4. Dikusar, E.A., Kozlov, N.G., Potkin, V.I., Yuvchenko, A.P., and Tlegenov, R.T., Zameshchennye benzal’degidy vanilinovogo ryada v organicheskom sinteze: poluchenie, primenenie, biologicheskaya aktivnost’ (Substituted Benzaldehydes of the Vanillin Series in Organic Synthesis: Synthesis, Application, and Biological Activity), Minsk: Pravo i Ekonomika, 2011; Dikusar, E.A., Potkin, V.I., and Kozlov, N.G., Benzal’degidy vanilinovogo ryada. Sintez proizvodnykh, primenenie i biologicheskaya aktivnost’ (Benzaldehydes of the Vanillin Series. Synthesis of Derivatives, Application, and Biological Activity), Saarbrücken, Germany: LAP LAMBERT Academic, 2012.

    Google Scholar 

  5. Vatsuro K.V. and Mishchenko, G.L., Imennye reaktsii v organicheskoi khimii (Name Reactions in Organic Chemistry), Moscow: Khimiya, 1976.

    Google Scholar 

  6. Singh, T.D. and Taft, R.W., J. Am. Chem. Soc., 1975, vol. 97, p. 3867.

    Article  CAS  Google Scholar 

  7. Potkin, V.I., Gadzhily, R.A., Dikusar, E.A., Petkevich, S.K., Zhukovskaya, N.A., Aliev, A.G., and Nagieva, Sh.F., Russ. J. Org. Chem., 2012, vol. 48, p. 127.

    Article  CAS  Google Scholar 

  8. Dyer, J.R., Applications of Absorption Spectroscopy of Organic Compounds, Englewood Cliffs: Prentice-Hall, 1965. Translated under the title Prilozheniya absorbtsionnoi spektroskopii organicheskikh soedinenii, Moscow: Khimiya, 1970, p. 92.

    Google Scholar 

  9. Katritzky, A.R., Kuanar, M., Slavov, S., Dobchev, D.A., Fara, D.C., Karelson, M., Acree, W.E., Solov’ev, V.P., and Varnek, A., Bioorg. Med. Chem., 2006, vol. 14, p. 4888; Baskin, I.I., Buznikov, G.A., Kabankin, A.S., Landau, M.A., Leksina, L.A., Ordukhanyan, A.A., Palyulin, V.A., and Zefirov, N.S., Izv. Akad. Nauk, Ser. Biol., 1997, p. 407.

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Institute of Physical Organic Chemistry, National Academy of Sciences of Belarus, ul. Surganova 13, Minsk, 220072, Belarus

    E. A. Dikusar, V. I. Potkin, S. K. Petkevich & T. D. Zvereva

  2. Institute of Polymeric Materials, National Academy of Sciences of Azerbaijan, Sumgait, Azerbaijan

    R. A. Gadzhily, A. G. Aliev & L. Ya. Gadzhieva

Authors
  1. E. A. Dikusar
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. R. A. Gadzhily
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. V. I. Potkin
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. S. K. Petkevich
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. T. D. Zvereva
    View author publications

    You can also search for this author in PubMed Google Scholar

  6. A. G. Aliev
    View author publications

    You can also search for this author in PubMed Google Scholar

  7. L. Ya. Gadzhieva
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to E. A. Dikusar.

Additional information

Original Russian Text © E.A. Dikusar, R.A. Gadzhily, V.I. Potkin, S.K. Petkevich, T.D. Zvereva, A.G. Aliev, L.Ya. Gadzhieva, 2013, published in Zhurnal

Organicheskoi Khimii, 2013, Vol. 49, No. 10, pp. 1537–1542.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Dikusar, E.A., Gadzhily, R.A., Potkin, V.I. et al. Synthesis of functionally substituted isoxazole-containing benzaldehydes of the vanillin series and Schiff bases derived therefrom. Russ J Org Chem 49, 1517–1522 (2013). https://doi.org/10.1134/S1070428013100199

Download citation

  • Received:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1134/S1070428013100199

Keywords

Search

Navigation