Skip to main content
SpringerLink
Log in

Single-stage synthesis of 3-hydroxy- and 3-alkoxy-5-arylimidazolidine-2,4-diones by reaction of arylglyoxal hydrates with N-hydroxy- and N-alkoxyureas

  • Published:
Chemistry of Heterocyclic Compounds Aims and scope

Arylglyoxal hydrates interact with N-alkoxyureas and N-hydroxyurea in acetic acid with selective formation of 3-alkoxy-5-arylimidazolidine-2,4-diones and 5-aryl-3-hydroxyimidazolidine-2,4-diones, respectively. The structures of 3-methoxy-5-phenylimidazolidine-2,4-dione, 3-ethoxy-5-phenylimidazolidine-2,4-dione, and 3-butoxy-5-(4-chlorophenyl)imidazolidine-2,4-dione were studied by X-ray structural analysis.

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

Figure 1
Figure 2
Figure 3

Similar content being viewed by others

References

  1. Aspelund, H. Acta Acad. Abo., Ser. B. 1962, 23, 22.

    Google Scholar 

  2. Aspelund, H.; Waselius P. Acta Acad. Abo., Ser. B. 1967, 27, 18.

    Google Scholar 

  3. Petersen, H. Synthesis 1973, 243.

  4. Nelyubina, Yu. V.; Gazieva, G. A.; Baranov, V. V.; Belyakov, P. A.; Chizhov, A. O., Lyssenko, K. A.; Kravchenko, A. N. Russ. Chem. Bull., Int. Ed. 2009, 58, 1353. [Izv. Akad. Nauk, Ser. Khim. 2009, 1315.]

  5. Shtamburg, V. G.; Anishchenko, A. A.; Shtamburg, V. V.; Shishkin, O. V.; Zubatyuk, R. I.; Mazepa, A. V.; Rakipov, Kostyanovsky, R. G. Mendeleev Commun. 2008, 18, 102.

  6. Kostyanovsky, R. G.; Shtamburg, V. G.; Shishkin, O. V.; Zubatyuk, R. I.; Shtamburg, V. V.; Anishchenko, A. A.; Mazepa, A. V. Mendeleev Commun. 2010, 20, 167.

    Article  CAS  Google Scholar 

  7. Simet, L.; Reisner, D. B.; Ludwig, B. J.; Duersch, F.; Berger, F. M. J. Med. Chem. 1970, 13, 1067.

    Article  CAS  Google Scholar 

  8. Hurd, C. D.; Prapas, A. G. J. Am. Chem. Soc. 1958, 80, 6053.

    Article  CAS  Google Scholar 

  9. Call, L. Monatsh. Chem., 1970, 101, 228.

    Article  CAS  Google Scholar 

  10. Teramoto, T.; Kurosaki, T.; Okawara, M. Tetrahedron Lett. 1977, 18, 1523.

    Article  Google Scholar 

  11. Jones, J. H.; Witty, M. J. J. Chem. Soc., Perkin Trans. 1 1980, 585.

  12. Tanaka, K.; Matsuo, K.; Nakanishi, A.; Kataoka, Y.; Takase, K.; Otsuki, S. Chem. Pharm. Bull. 1988, 36, 2323.

    Article  CAS  Google Scholar 

  13. Vystorop, I. V.; Lyssenko, K. A.; Kostyanovsky, R. G. Mendeleev Commun. 2003, 13, 116.

    Article  Google Scholar 

  14. Winkler, F. K.; Dunitz, J. D. J. Mol. Biol. 1971, 59, 169.

    Article  CAS  Google Scholar 

  15. Zefirov, Yu. V.; Zorkiy, P. M. Usp. Khim. 1989, 58, 713.

    Article  CAS  Google Scholar 

  16. Synthesis of Organic Compounds [Russian translation], Kazansky, B. A., Ed.; Mir: Moscow, 1964, Vol. 12, p. 121.

  17. Shtamburg, V. G.; Kostyanovsky, R. G.; Tsygankov, A. V.; Shtamburg, V. V.; Shishkin, O. V.; Zubatyuk, R. I.; Mazepa, A. V.; Kravchenko, S. V. Izv. Akad. Nauk, Ser. Khim. 2015, 62.

  18. Shtamburg, V. G.; Klots, E. A.; Pleshkova, A. P.; Avramenko,V. I.; Ivonin, S. P.; Tsygankov, A. V.; Kostyanovsky, R. G. Russ. Chem. Bull., Int. Ed. 2003, 52, 2251. [Izv. Akad. Nauk, Ser. Khim. 2003, 2132.]

  19. Kipnis, F.; Ornfelt, J. J. Am. Chem. Soc. 1946, 68, 2734.

    Article  CAS  Google Scholar 

  20. Riley, H. L.; Morley, J. F.; Friend, N. A. C. J. Chem. Soc., 1932, 1875.

  21. Sheldrick, G. Acta Crystallogr., Sect. A: Found. Crystallogr. 2008, A64, 112.

    Article  Google Scholar 

  22. Grimme, S. J. Comput. Chem. 2006, 27, 1787.

    Article  CAS  Google Scholar 

  23. Grimme, S.; Antony, J.; Ehrlich, S.; Krieg, H. J. Chem. Phys. 2010, 132, 154104.

    Article  Google Scholar 

  24. Grimme, S.; Ehrlich, S.; Goerigk, L. J. Comput. Chem. 2011, 32, 1456.

    Article  CAS  Google Scholar 

  25. Schaufer, A.; Horn, H.; Ahlrichs, R. J. Chem. Phys. 1992, 97,.

  26. Weigend, F.; Ahlrichs, R. Phys. Chem. Chem. Phys. 2005, 7,.

  27. Neese, F. Wiley Interdiscip. Rev.: Comput. Mol. Sci. 2012, 2,73.

Download references

This work received financial support from the Ministry of Education and Science of Ukraine (grant 0115U003159), Ukraine State Foundation for Basic Research (grant F-53.3/001), and the Russian Foundation for Basic Research (grant 13-03-90460).

Author information

Authors and Affiliations

  1. Ukrainian State University of Chemical Technologies, 8 Gagarina Ave., Dnipropetrovsk, 49005, Ukraine

    Vasiliy G. Shtamburg & Viktor V. Shtamburg

  2. Oles’ Gonchar Dnipropetrovsk National University, 25 Nauchnaya St., Dnipropetrovsk, 49050, Ukraine

    Andrey A. Anishchenko

  3. State Scientific Institution “Institute for Single Crystals” of National Academy of Sciences of Ukraine, 60 Lenina Ave., Kharkiv, 61001, Ukraine

    Roman I. Zubatyuk

  4. A. V. Bogatskii Physicochemical Institute, National Academy of Sciences of Ukraine, 86 Lyustdorfskaya Road, Odessa, 65060, Ukraine

    Aleksander V. Mazepa

  5. Kirovohrad Volodymyr Vinnichenko State Pedagogical University, 1 Shevchenko St., Kirovohrad, 25006, Ukraine

    Eugene A. Klotz

  6. Dnipropetrovsk State Agrarian and Economic University, Voroshilova str. 25, Dnipropetrovsk, 49600, Ukraine

    Svetlana V. Kravchenko

  7. N. N. Semenov Institute of Chemical Physics, Russian Academy of Sciences, 4 Kosygina St., Moscow, 119991, Russia

    Remir G. Kostyanovsky

Authors
  1. Vasiliy G. Shtamburg
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Viktor V. Shtamburg
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Andrey A. Anishchenko
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Roman I. Zubatyuk
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. Aleksander V. Mazepa
    View author publications

    You can also search for this author in PubMed Google Scholar

  6. Eugene A. Klotz
    View author publications

    You can also search for this author in PubMed Google Scholar

  7. Svetlana V. Kravchenko
    View author publications

    You can also search for this author in PubMed Google Scholar

  8. Remir G. Kostyanovsky
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Vasiliy G. Shtamburg.

Additional information

Translated from Khimiya Geterotsiklicheskikh Soedinenii, 2015, 51(6), 553–559

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Shtamburg, V.G., Shtamburg, V.V., Anishchenko, A.A. et al. Single-stage synthesis of 3-hydroxy- and 3-alkoxy-5-arylimidazolidine-2,4-diones by reaction of arylglyoxal hydrates with N-hydroxy- and N-alkoxyureas. Chem Heterocycl Comp 51, 553–559 (2015). https://doi.org/10.1007/s10593-015-1735-0

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s10593-015-1735-0

Keywords

Search

Navigation