Skip to main content
SpringerLink
Log in

Three-component condensation of α-nitroacetophenone, aromatic aldehydes, and methylurea

  • Published:
Russian Chemical Bulletin Aims and scope

Abstract

The three-component condensation of aromatic aldehydes, methylurea, and α-nitroacetophenone affords both N(1)-and N(3)-methyl-substituted 4,6-diaryl-5-nitro-3,4-dihydropyrimidin-2(1H)-ones depending on the structure of aldehyde. Intermediate 4,6-diaryl-4-hydroxy-3-methyl-5-nitrohexahydropyrimidin-2-ones and trisubstituted urea, which is the transformation product of the 4-hydroxy-3-methyl derivative in an acidic medium (retro-Henry reaction), were identified in the reaction mixtures.

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

Similar content being viewed by others

References

  1. D. A. Horton, G. T. Bourn, and M. L. Smythe, Chem. Rev., 2003, 103, 893.

    Article  CAS  Google Scholar 

  2. C. O. Kappe, Acc. Chem. Res., 2000, 33, 879.

    Article  CAS  Google Scholar 

  3. C. O. Kappe, Eur. J. Med. Chem., 2000, 35, 1043.

    Article  CAS  Google Scholar 

  4. A. O. Bryzgalov, M. P. Dolgikh, I. V. Sorokina, T. G. Tolstikova, V. F. Sedova, and O. P. Shkurko, Bioorg. Med. Chem. Lett., 2006, 16, 1418.

    Article  CAS  Google Scholar 

  5. PCT Int. Appl. 2006 097617; PCT Int. Appl. 2005 009392; Chem. Abstrs, 2005, 142, 198087; PCT Int. Appl. 98 51311; Chem. Abstrs, 1999, 130, 25077.

    Google Scholar 

  6. PCT Int. Appl. 2005 82863; Chem. Abstrs, 2005, 143, 286440; (b) PCT Int. Appl. 2005 82864; Chem. Abstrs, 2005, 143, 286441; (c) PCT Int. Appl. 98 33791; Chem. Abstrs, 1998, 129, 148989.

  7. PCT Int. Appl. 00 06565; Chem. Abstrs, 2000, 132, 137405.

    Google Scholar 

  8. C. O. Kappe, Tetrahedron, 1993, 49, 6937; A. Stadler and C. O. Kappe, J. Comb. Chem., 2001, 3, 624.

    Article  CAS  Google Scholar 

  9. K. Singh, D. Arora, and S. Singh, Tetrahedron Lett., 2006, 47, 4205; (b) H. Salehi and Q.-X. Guo, Synth. Commun., 2004, 34, 171; (c) M. J. Lusch and J. A. Tallarico, Org. Lett., 2004, 6, 3237; (d) A. Dondoni and A. Massi, Molecular Diversity, 2003, 6, 261; (e) S. A. Kravchenko, V. V. Pirozhenko, S. I. Vdovenko, A. E. Sorochinskii, and G. Ya. Remennikov, Khim. Geterotsikl. Soedin., 2003, 216 [Chem. Heterocycl. Compd., 2003, 39, 188 (Engl. Transl.)]; (f) F. S. Falsone and C. O. Kappe, ARKIVOC, 2001, 122; (g) H. Namazi, Y. R. Mirzaei, and H. Azamat, J. Heterocycl. Chem., 2001, 38, 1051.

    Article  CAS  Google Scholar 

  10. A. R. Marzinzik and E. R. Felder, J. Org. Chem., 1998, 63, 723.

    Article  CAS  Google Scholar 

  11. E. S. Putilova, G. V. Kryshtal’, G. M. Zhdankina, N. A. Troitskii, and S. G. Zlotin, Zh. Org. Khim., 2005, 41, 524 [Russ. J. Org. Chem., 2005, 41, 512 (Engl. Transl.)].

    Google Scholar 

  12. V. F. Sedova, T. V. Voevoda, T. G. Tolstikova, and O. P. Shkurko, Khim.-farm. Zh., 2002, 36, No. 6, 4 [Pharm. Chem. J., 2002, 36, 284 (Engl. Transl.)].

    Google Scholar 

  13. C. O. Kappe and P. Roscher, J. Heterocycl. Chem., 1989, 26, 55.

    Article  CAS  Google Scholar 

  14. V. F. Sedova, V. P. Krivopalov, and O. P. Shkurko, Zh. Org. Khim., 2007, 43, 87 [Russ. J. Org. Chem., 2007, 43, 90 (Engl. Transl.)].

    Google Scholar 

  15. E. S. Putilova, N. A. Troitskii, S. G. Zlotin, O. G. Khudina, Ya. V. Burgart, V. I. Saloutin, and O. N. Chupakhin, Zh. Org. Khim., 2006, 42, 1407 [Russ. J. Org. Chem., 2006, 42, 1392 (Engl. Transl.)]; V. A. Mamedov, L. V. Mustakimova, I. T. Gubaidullin, S. V. Vdovina, I. A. Litvinov, and V. S. Reznik, Khim. Geterotsikl. Soedin., 2006, 1414 [Chem. Heterocycl. Compd., 2006, 42, 1229 (Engl. Transl.)].

    Google Scholar 

  16. C. O. Kappe, J. Org. Chem., 1997, 62, 7201.

    Article  CAS  Google Scholar 

  17. M. V. Pryadeina, Ya. V. Burgart, M. I. Kodess, V. I. Saloutin, and O. N. Chupakhin, Izv. Akad. Nauk, Ser. Khim., 2004, 1210 [Russ. Chem. Bull., Int. Ed., 2004, 53, 1261].

    Google Scholar 

  18. G. Ya. Remennikov, I. V. Boldyrev, N. A. Kapran, and L. K. Kurilenko, Khim. Geterotsikl. Soedin., 1993, 388 [Chem. Heterocycl. Compd., 1993, 29, 325 (Engl. Transl.)].

  19. F. Sweet and J. D. Fissekis, J. Am. Chem. Soc., 1973, 95, 8741.

    Article  CAS  Google Scholar 

  20. Z. D. Aron and L. E. Overman, Chem. Commun., 2004, 253.

Download references

Author information

Authors and Affiliations

  1. N. N. Vorozhtsov Novosibirsk Institute of Organic Chemistry, Siberian Branch of the Russian Academy of Sciences, 9 prosp. Akad. Lavrent’eva, 630090, Novosibirsk, Russian Federation

    V. F. Sedova, V. P. Krivopalov & O. P. Shkurko

Authors
  1. V. F. Sedova
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. V. P. Krivopalov
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. O. P. Shkurko
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to O. P. Shkurko.

Additional information

Dedicated to the memory of Academician N. N. Vorozhtsov on the 100th anniversary of his birth.

Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 6, pp. 1141–1145, June, 2007.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Sedova, V.F., Krivopalov, V.P. & Shkurko, O.P. Three-component condensation of α-nitroacetophenone, aromatic aldehydes, and methylurea. Russ Chem Bull 56, 1184–1189 (2007). https://doi.org/10.1007/s11172-007-0180-3

Download citation

  • Received:

  • Revised:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11172-007-0180-3

Key words

Search

Navigation