Skip to main content
Log in

Reaction of 4-hydroxycoumarin with arylglyoxals and ureas

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

Abstract

One-pot condensation of 4-hydroxycoumarin with arylglyoxals and ureas gave 4-aryl-5-(4-hydroxy-2-oxo-2H-chromen-3-yl)-1H-imidazol-2(3H)-ones. The same compounds may be obtained from aroylbis(4-hydroxy-2-oxo-2H-chromen-3-yl)methanes and urea. The reaction of 4-bromobenzaldehyde with 4-hydroxycoumarin in the presence of urea led to the formation of the corresponding Michael adduct without participation of urea.

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. Manolov, I., Maichle-Moessmer, C., and Danchev, N., Eur. J. Med. Chem., 2006, vol. 41, p. 882.

    Article  CAS  Google Scholar 

  2. Manolov, I., Maichle-Moessmer, C., Nicolova, I., and Danchev, N., Arch. Pharm., 2006, vol. 336, p. 319.

    Article  CAS  Google Scholar 

  3. Belikov, V.G., Farmatsevticheskaya khimiya (Pharmaceutical Chemistry), Moscow: Vysshaya Shkola, 1993.

    Google Scholar 

  4. Jackson, S.A., Sahni, S., Lee, L., Luo, Y., and Nieduzak, T.R., Bioorg. Med. Chem., 2005, vol. 13, p. 2723.

    Article  CAS  Google Scholar 

  5. Choudhary, M., Fatima, N., Khan, K., Jalil, S., Iqbal, S., and Rahman, A., Bioorg. Med. Chem., 2006, vol. 14, p. 8066.

    Article  CAS  Google Scholar 

  6. Sandeep, A., Devanand, B., and Shinde, R., Bioorg. Med. Chem. Lett., 2006, vol. 16, p. 6181.

    Article  CAS  Google Scholar 

  7. Cravotto, G., Tagliapietra, S., Cappelo, R., Palmisano, G., Curini, M., and Boccalini, M., Arch. Pharm., 2006, vol. 336, p. 129.

    Article  CAS  Google Scholar 

  8. Hamdi, M., Grech, O., Sakellariou, R., and Speziale, V., J. Heterocycl. Chem., 1994, vol. 31, p. 509.

    CAS  Google Scholar 

  9. Hamdi, N., Lidressi, C., Saoud, M., Nievas, A.R., and Zarrouk, H., J. Heterocycl. Chem., 2006, vol. 42, p. 36.

    Google Scholar 

  10. Burgart, Ya.V., Shcherbakov, K.V., Saloutin, V.I., and Chupakhin, O.N., Izv. Ross. Akad. Nauk, Ser. Khim., 2004, p. 1188.

  11. Tonkina, N., Petrova, M., Belyakov, S., and Strakovs, A., Latv. Khim. Z., 2005, vol. 1, p. 51.

    Google Scholar 

  12. Kolos, N.N., Gozalishvili, L.L., Yaremenko, F.G., Shishkin, O.V., Shishkina, S.V., and Konovalova, I.S., Izv. Ross. Akad. Nauk, Ser. Khim., 2007, p. 2200.

  13. Staunton, J., Comprehensive Organic Chemistry, Barton, D. and Ollis, W.D., Eds., Oxford: Pergamon, 1979, vol. 5. Translated under the title Obshchaya organicheskaya khimiya, Moscow: Khimiya, 1985, vol. 9, p. 62.

    Google Scholar 

  14. Kidwai, M., Saxena, S., and Mohan, R., Russ. J. Org. Chem., 2006, vol. 42, p. 52.

    Article  CAS  Google Scholar 

  15. Balalaie, S., Soleiman-Beigi, M., and Rominger, F., J. Iran. Chem. Soc., 2005, vol. 2, p. 319.

    CAS  Google Scholar 

  16. Fisher, H.J., Ekeley, J.B., and Ronzio, A.R., J. Am. Chem. Soc., 1942, vol. 64, p. 1434.

    Article  CAS  Google Scholar 

  17. Joshi, K.G., Pathal, V.N., and Goyal, M.K., J. Heterocycl. Chem., 1981, vol. 18, p. 1651.

    CAS  Google Scholar 

  18. Hough, T.L., Hough, I.R., and Pannell, R.W., J. Heterocycl. Chem., 1986, vol. 23, p. 1125.

    Article  CAS  Google Scholar 

  19. Dabiri, M., Delbari, A.S., and Bazgir, A., Synlett, 2007, p. 821.

  20. Liao, Y.X. and Kuo, P.Y., Tetrahedron Lett., 2003, vol. 44, p. 1599.

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to N. N. Kolos.

Additional information

Original Russian Text © N.N. Kolos, L.L. Gozalishvili, E.N. Sivokon’, I.V. Knyazeva, 2009, published in Zhurnal Organicheskoi Khimii, 2009, Vol. 45, No. 1, pp. 124–129.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Kolos, N.N., Gozalishvili, L.L., Sivokon’, E.N. et al. Reaction of 4-hydroxycoumarin with arylglyoxals and ureas. Russ J Org Chem 45, 119–125 (2009). https://doi.org/10.1134/S1070428009010151

Download citation

  • Received:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1134/S1070428009010151

Keywords

Navigation