One-pot synthesis of the substituted imidazolidin-2-ones with participation of thiobarbituric acid, ureas and arylglyoxals

Authors

  • N. M. Kolos V.N.Karazin Kharkiv National University, Ukraine
  • L. L. Zamigaylo DNU "NTK" Institute of Single Crystals "of the National Academy of Sciences of Ukraine, Ukraine
  • N. V. Chechina V.N.Karazin Kharkiv National University, Ukraine

DOI:

https://doi.org/10.24959/ophcj.13.742

Keywords:

imidozoline-2-ones, one-pot synthesis, tautomerism, thiobarbituric acid, arylglyoxals, ureas

Abstract

Derivatives of imidozoline-2-ones containing the pyrimidinthionic moiety in position 4 have been synthesized by three-component one-pot condensation of thiobarbituric acid, arylglyoxal hydrates and ureas. It has been found that these compounds exist in the solution of DMSO-d6 as a mixture of two tautomeric forms: for products obtained from N-substituted ureas the imidazolidin form predominates; and in the case of urea the imidazolidin and imidazolin forms are present in the ratio of 1:1.

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References

  1. Bellina F., Cauteruccio S., Rossi R. // Tetrahedron. − 2007. − Vol. 63, №22. − P. 4571-4624.
  2. Sharma D., Narasimhan B., Kumar P. et al. // Eur. J. Med. Chem. − 2009. − Vol. 44, №6. − P. 2347-2353.
  3. Puratchikodya A., Doble M. // Bioorg. Med. Chem. – 2007. − Vol. 15. − P. 1083-1090.
  4. Malhotra V., Pathak S.R., Nath R. et al. // Bioorg. Med. Chem. Lett. – 2011. − Vol. 21, №3. − P. 936-939.
  5. Gupta P., Hameed S., Jain R. // Eur. J. Med. Chem. − 2004. − Vol. 39. − P. 895-814.
  6. Sharma S.D., Hazarika P., Konwar D. // Tetrahedron Lett. – 2008. − Vol. 49, №14. − P. 2216-2220.
  7. Khalafi-Nezhad A., Soltani M.N., Hakimelahi G.H., Mokhtari B. // Tetrahedron. – 2002. − Vol. 58, №52. − P. 10341-10344.
  8. Robert J.H., Sabourina C., Alvarez N. et al. // Eur. J. Med. Chem. – 2003. – Vol. 38. − P. 711-718.
  9. Özkay Y., Iskar I., Incesu Z., Akalın G. // Eur. J. Med. Chem. – 2010. – Vol. 45. − P. 1-9.
  10. Refaat H.M. // Eur. J. Med. Chem. – 2010. – Vol. 45. − P. 2949-2956.
  11. Congiu C., Cocco M.T., Onnis V. // Bioorg. Med. Chem. Lett. – 2008. − Vol. 18, №3. − P. 989-993.
  12. Hadizadeh F., Hosseinzadeh H., Motamed-Shariaty V. et al. // Iran. J. Pharm. Res. – 2008. – Vol. 7, №1. − P. 29-33.
  13. Librowski T., Filipex B., Czamecki R. // Act. Pol. Pharm. – 2000. − Vol. 57, №5. − P. 391-396.
  14. Peretto I., Fortani R., Fossati G. et al. // J. Med. Chem. − 2007. − Vol. 50, №7. − P. 1693-1697.
  15. Jablonowski A.J., Ly K.S., Bogenstaetter M. et al. // Bioorg. Med. Chem. Lett. – 2009. − Vol. 19, №3. − P. 903-907.
  16. Laufer S., Hauser D., Stegmiller T. et al. // Bioorg. Med. Chem. Lett. – 2010. − Vol. 20, №22. − P. 6671-6675.
  17. 17 Kolos N.N., Gozalishvili L.L., Sivokon E.N., Knyazeva I.V. // Russ. J. Org. Chem. – 2009. − Vol. 45, №1. − P. 119-125.
  18. Замігайло Л.Л., Колос Н.М. // Вісник ХНУ ім. В.Н.Каразіна. – 2008. – №820. – Вип. 16 (39). – С. 241-245.
  19. Gozalishvili L.L, Beryozkina T.V. et al. // Tetrahedron. – 2008. – Vol. 64. – P. 8759-8765.
  20. Moskvin А.V., Polcovnikova I.I., Ivin B.А. // Russ. J. Org. Chem. – 1998. – Vol. 68. – Р. 801-805.
  21. Колос Н.Н., Замигайло Л.Л., Чечина Н.В. и др. // ХГС. – 2012. – №12. – С. 1461-1467.
  22. Колос Н.Н., Замигайло Л., Мусатов В.И. // ХГС. − 2009. − №8. – С. 1220-1226.
  23. Fisher H.J., Ekeley J.B., Ronzio A.R. // J. Am. Chem. Soc. – 1942. – Vol. 64. – P. 1434-1436.

Published

2013-09-10

How to Cite

(1)
Kolos, N. M.; Zamigaylo, L. L.; Chechina, N. V. One-Pot Synthesis of the Substituted Imidazolidin-2-Ones With Participation of Thiobarbituric Acid, Ureas and Arylglyoxals. J. Org. Pharm. Chem. 2013, 11, 72-77.

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Section

Original Researches