Synthesis of pyrimidine-2,4,6-trion and 2-thioxo-pyrimidin-4,6-dione with imidazolidine fragment

  • Nadiia N. Kolos V.N. Karazin Kharkiv National University https://orcid.org/0000-0002-7520-656X
  • Dmitry I. Nikishin V.N. Karazin Kharkiv National University
  • Natalia V. Chechina V.N. Karazin Kharkiv National University
  • Lali L. Zamigaylo V.N. Karazin Kharkiv National University
Keywords: N,N-dimethylbarbituric acid, thiobarbituric acid, aliphatic glyoxals, R-ureas, imidazolidine-2-ones, tetraazаspiro[5.5]undec-4-ene, one-pot synthesis

Abstract

Pyrimidine-2,4,6-trion (2-thioxopyrimidine-4,6-dione) with imidazolidine cycle in position 5 have been synthesized by the three-component condensation of aliphatic glyoxals, N,N-dimethylbarbituric (thiobarbituric) acid and ureas. Tetraazаspiro[5.5]undec-4-ene is shown to form  in the reaction of N,N-dimethylbarbituric acid, hydrate glyoxal and N,N-dimethylurea.

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References

Bellina F., Cauteruccio S., Rossi R. // Tetrahedron. −2007.− Vol. 63, № 22.− P. 4571-4624.

Sharma D., Narasimhan B., Kumar P., Judge V. et all.// Eur. J. Med. Chem.−2009. −Vol. 44, № 6.− P. 2347-2353.

Puratchikodya A. and Doble M. // Bioorg. Med. Chem.–2007.− Vol. 15, − P. 1083–1090.

Malhotra V., Pathak S., Nath R., Mukherjee D., Shanker K.// Bioorg. Med. Chem. Lett. – 2011. − Vol. 21, № 3.− P. 936-939.

Gupta P., Hameed S., Jain R. // Eur. J. Med. Chem. −2004. − Vol. 39. −P. 895-814.

Sharma S.D., Hazarika P., Konwar D. // Tetrahedron Lett. –2008. −Vol. 49, № 14.− P. 2216-2220.

Khalafi-Nezhad A., Soltani M. N, Hakimelahi G. H, Mokhtari B. // Tetrahedron. –2002. −Vol. 58, № 52. −P. 10341-10344.

Robert J. H., Sabourina C., Alvarez N., Piessard S.R., Le Baut G., LePape P. // Eur. J. Med. Chem. –2003. – Vol.38. − P. 711-718.

Özkay Y., Iskar I., Incesu Z., Akalın G. // Eur. J. Med. Chem. – 2010. – Vol.45. − P. 1-9.

Refaat H. M. // Eur. J. Med. Chem. – 2010. – Vol.45. − P.2949-2956.

Congiu C., Cocco M. T., Onnis V. // Bioorg. Med. Chem. Lett. – 2008. − Vol. 18, № 3.− P. 989-993.

Hadizadeh F., Hosseinzadeh H., Motamed-Shariaty V., Seifi M., Kazemi S. // Iran. J. Pharm. Res.– 2008. – Vol.7, № 1.− P.29−33.

Librowski T., Filipex B., Czamecki R. // Act. Pol. Pharm. – 2000. −Vol.57,№ 5.− P.391−396.

Peretto I., Fortani R., Fossati G., Giardina G. et all. // J. Med. Chem. −2007. − Vol. 50, №7.− P. 1693-1697.

Jablonowski A. J., Ly K. S., Bogenstaetter M., Dvorak C. A., Boggs J. D. et all. // Bioorg. Med. Chem. Lett. – 2009. − Vol. 19, № 3.− P. 903-907.

Laufer S, Hauser D., Stegmiller T., Bracht C., Ruff K. et all. // Bioorg. Med. Chem. Lett. – 2010. − Vol. 20, № 22.− P. 6671-6675.

Kolos N. N., Gozalishvili L. L., Sivokon E. N., Knyazeva I. V. // Russian J. Org. Chem. –2009. − Vol. 45, № 1.−P. 119-125.

Zamigaylo L. L., Kolos N. M. // Kharkov university Bulletin. - 2008. - № 820. – Iss. 16 (39). - Р. 241-245.

Kolos N. N., Zamigaylo L. L., Chechina N. V., Omelchenko I. V., Shishkin O. V., Vaschenko E. V. // Chem. Heterocycl. Comp. - 2013.- Vol. 48, №12. -Р. 1817-1823.

Kolos N. M., Chechina N. V., Zamigaylo L. L. // J. Org. Pharm. Chem. – 2013.- Vol. 11, №3 (43). -P. 72-77.

Gozalishvili L. L, Beryozkina T. V., Omelchenko I. V., Zubatyuk R. I., Shishkin O. V., Kolos N. N. // Tetrahedron. 2008. – Vol. 64. – P. 8759–8765.

Moskvin А.V., Polcovnikova I. I., Ivin B. А. // Russian J. Org. Chem.– 1998. – Vol. 68. – Р. 801–805.

Fisher H. J., Ekeley J. B., Ronzio A. R. // J. Am. Chem. Soc. – 1942. – Vol. 64. – P. 1434–1436

Published
2013-12-20
Cited
How to Cite
Kolos, N. N., Nikishin, D. I., Chechina, N. V., & Zamigaylo, L. L. (2013). Synthesis of pyrimidine-2,4,6-trion and 2-thioxo-pyrimidin-4,6-dione with imidazolidine fragment. Kharkiv University Bulletin. Chemical Series, (22), 45-52. https://doi.org/10.26565/2220-637X-2013-22-05