Skip to main content
Log in

Synthesis of hydroxybenzaldehyde derivatives containing an isoxazole heteroring

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

Abstract

5-Phenyl(p-tolyl)isoxazole-3-carboxylic acids were synthesized starting from 3-hydroxyiminomethyl-5-phenyl(p-tolyl)isoxazoles, and their reactions with p-hydroxybenzaldehyde, vanillin, isovanillin, o-vanillin, and ethyl vanillin gave the corresponding esters. The latter were brought into condensation with aromatic amines to obtain Schiff bases which were reduced to amines.

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.

Institutional subscriptions

Similar content being viewed by others

References

  1. Eddington, N., Cox, D.S., Roberts, R.R., Butcer, R.J., Edafiogho, I.O., Stables, J.P., Cook, N., Goodwin, A.M., Smith, C.A., and Scott, K.R., Eur. J. Med. Chem., 2002, vol. 37, p. 635; Li, W.-T., Hwang, D.R., Chen, Ch.-P., Shen, Ch.-W., Huang, C.-L., Chen, T.-W., Lin, C.-H., Chang, Y.-L., Chang, Y.-Y., Chang, Y.-K., Lo, Y.-K., Tseng, H.-Y., Lin, C.-C., Song, J.-S., Chen, S.-J., Wu, S.-H., and Chen, C.-T., J. Med. Chem., 2003, vol. 46, p. 1706; Dallanoce, C., Frigerio, F., De Amici, M., Dorsch, S., Klotz, K.N., and De Micheli, C., Bioorg. Med. Chem., 2007, vol. 15, p. 2533.

    Article  CAS  Google Scholar 

  2. Durant, S. and Karran, P., Nucl. Acids Res., 2003, vol. 31, p. 5501.

    Article  CAS  Google Scholar 

  3. Petkevich, S.K., Potkin, V.I., and Kaberdin, R.V., Russ. J. Org. Chem., 2004, vol. 40, p. 1146.

    Article  CAS  Google Scholar 

  4. Potkin, V., Zubenko, Y., Bykhovetz, A., Zolotar, R., and Goncharuk, V., Nat. Prod. Commun., 2009, vol. 4, p. 1205.

    CAS  Google Scholar 

  5. Dikusar, E.A., Kozlov, N.G., Potkin, V.I., Yuvchenko, A.P., and Tlegenov, R.T., Zameshchennye benzaldegidy vanilinovogo ryada v organicheskom sinteze: poluchenie, primenenie, biologicheskaya aktivnost’ (Substituted Benzaldehydes of the Vanillin Series in Organic Synthesis: Preparation, Application, and Biological Activity), Minsk: Pravo i Ekonomika, 2011.

    Google Scholar 

  6. 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 

Download references

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to V. I. Potkin.

Additional information

Original Russian Text © V.I. Potkin, R.A. Gadzhily, E.A. Dikusar, S.K. Petkevich, N.A. Zhukovskaya, A.G. Aliev, Sh.F. Nagieva, 2012, published in Zhurnal Organicheskoi Khimii, 2012, Vol. 48, No. 1, pp. 132–141.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Potkin, V.I., Gadzhily, R.A., Dikusar, E.A. et al. Synthesis of hydroxybenzaldehyde derivatives containing an isoxazole heteroring. Russ J Org Chem 48, 127–136 (2012). https://doi.org/10.1134/S1070428012010216

Download citation

  • Received:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1134/S1070428012010216

Keywords

Navigation