Skip to main content
SpringerLink
Log in

Nitromethylidene-containing piperazinones and morpholinone: synthesis and structure

  • SHORT COMMUNICATIONS
  • Published:
Chemistry of Heterocyclic Compounds Aims and scope

The interactions of alkyl 3-bromo-3-nitroacrylates with 1,2-diaminoethane, 1,2-diaminopropane, 1,2-diaminocyclohexane, and 2-aminoethanol were shown to provide a convenient route for the synthesis of six-membered heterocycles – (3Z)-3-(nitromethylidene)-piperazin-2-ones and (3Z)-3-(nitromethylidene)morpholin-2-one. The structures of the synthesized heterocycles were characterized by a range of spectral methods and 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.
Figure 4.
Figure 5.

Similar content being viewed by others

References

  1. Andreichikov, Yu. S.; Tokmakova, T. N.; Pidémskii, E. L.; Voronova, L. A.; Vilenchik, Ya. M. Pharm. Chem. J. 1977, 11, 668.

    Article  Google Scholar 

  2. Milyutin, A. V.; Safonova, N. V.; Goleneva, A. F.; Andreichikov, Yu. S.; Tul'bovich, G. A.; Makhmudov, R. R. Pharm. Chem. J. 1994, 28, 915.

    Article  Google Scholar 

  3. Elzahhar, P. A. S.; Soliman, R.; AM El-Hawash, S. A. M.; Ragab, H. M. A.; Youssef, A. M.; Abdel Wahab, A. E. Med. Chem. 2015, 11, 407.

  4. Mullen, G. B.; Georgiev, V. St.; Acker, C. G. Heterocycles 1986, 24, 1285.

  5. Saloutin, V. I.; Skryabina, Z. E.; Basyl', I. T.; Kondrat'ev, P. N.; Chupakhin, O. N. J. Fluorine Chem. 1994, 69, 119.

    Article  CAS  Google Scholar 

  6. Zubkov, I. N.; Romanov, A. R.; Ushakov, I. A.; Rulev, A. Yu. Tetrahedron 2020, 76, 130884.

    Article  CAS  Google Scholar 

  7. Bagrov, F. V. Russ. J. Org. Chem. 1994, 30, 1768.

    Google Scholar 

  8. Biekert, E.; Hoffmann, D.; Enslein, L. Chem. Ber. 1961, 94, 2778.

    Article  CAS  Google Scholar 

  9. Saloutin, V. I.; Perevalov, S. G. J. Fluorine Chem. 1999, 96, 87.

    Article  CAS  Google Scholar 

  10. Fan, M.-J.; Li, G.-Q.; Liang, Y.-M. Tetrahedron 2006, 62, 6782.

    Article  CAS  Google Scholar 

  11. Fan, M.-J.; Li, G.-Q.; Li, L.-H.; Yang, S.-D.; Liang, Y.-M. Synthesis 2006, 2286.

  12. Iwanami, Y.; Kenjo, Y.; Nishibe, K.; Kajiura, M.; Isoyama, S. Bull. Chem. Soc. Jpn. 1964, 37, 1740.

    Article  CAS  Google Scholar 

  13. Iwanami, Y. Bull. Chem. Soc. Jpn. 1971, 44, 1311.

    Article  CAS  Google Scholar 

  14. Parr, R. W.; Reiss, J. A. Aust. J. Chem. 1984, 37, 389.

    Article  CAS  Google Scholar 

  15. Harwood, L. M.; Tucker, T. T.; Angell, R.; Finch, H. Tetrahedron Lett. 1996, 37, 4217.

    Article  CAS  Google Scholar 

  16. Berestovitskaya, V. M.; Tafeenko, V. A.; Makarenko S. V.; Sadikov, K. D.; Chernyshev I. V. Russ. J. Gen. Chem. 2006, 76, 135.

    Article  CAS  Google Scholar 

  17. Palmieri, A. Eur. J. Org. Chem. 2020, 28, 4247.

    Article  Google Scholar 

  18. Makarenko, S. V.; Sadykov, K. D.; Baichurin, R. I. Chem. Heterocycl. Compd. 2018, 54, 502.

    Article  CAS  Google Scholar 

  19. Stukan', E. V.; Makarenko, S. V.; Berkova, G. A.; Berestovitskaya, V. M. Russ. J. Gen. Chem. 2010, 80, 2460.

    Article  CAS  Google Scholar 

  20. Soengas, R. G.; Acurcio, R. C.; Silva, A. M. Eur. J. Org. Chem. 2014, 29, 6339.

    Article  Google Scholar 

  21. Rajappa, S. Tetrahedron 1981, 37, 1453.

    Article  CAS  Google Scholar 

  22. Rajappa, S. Tetrahedron 1999, 55, 7065.

    Article  CAS  Google Scholar 

  23. Gordon, A. J.; Ford, R. A. The Chemist's Companion; New York: Wiley, 1972.

    Google Scholar 

  24. Pedireddi, V. R.; Sarma, J. A. R. P.; Desiraju, G. R. J. Chem. Soc., Perkin Trans. 2 1992, 311.

  25. Shmoylova, Y. Yu.; Kovygin, Y. A.; Ledenyova, I. V.; Prezent, M. A.; Daeva, E. D.; Baranin, S. V.; Shikhaliev, K. S. Mendeleev Commun. 2021, 31, 259.

    Article  CAS  Google Scholar 

  26. Medvedeva, S. M.; Shikhlaliev, K. S.; Krysin, M. Y.; Gotsak, I. V. Chem. Heterocycl. Compd. 2016, 52, 309.

    Article  CAS  Google Scholar 

  27. Eften'eva, R. I.; Kushnir, O. V.; Lyavinets, O. S.; Mangalagiu, I. I.; Vovk, M. V. Monatsh. Chem. 2016, 147, 2127.

    Article  CAS  Google Scholar 

  28. Kuritsyna, M. A.; Pelipko, V. V.; Kataeva, O. N.; Baichurin, R. I.; Sadikov, K. D.; Smirnov, A. S.; Makarenko, S. V. Russ. Chem. Bull. 2021, 70, 1605.

    Article  CAS  Google Scholar 

  29. APEX2. Version 2.1; Bruker AXS, Inc.: Madison, 2006.

  30. SADABS; Bruker AXS, Inc.: Madison, 1997.

  31. Sheldrick, G. Acta Crystallogr., Sect. A: Found. Adv. 2015, A71, 3.

  32. Sheldrick, G. Acta Crystallogr., Sect. C: Struct. Chem. 2015, C71, 3.

  33. Spek, A. Acta Crystallogr., Sect. A: Found. Crystallogr. 1990, A46, 34.

  34. Farrugia, L. J. Appl. Crystallogr. 2012, 45, 849.

    Article  CAS  Google Scholar 

Download references

The physicochemical studies were performed on the equipment of Center for Collective Use ''Physical and chemical methods for the study of nitro compounds, coordination, biologically active substances and nanostructured materials'' at the Interdisciplinary Resource Center for Collective Use ''Modern physical and chemical methods for the formation and study of materials for the needs of industry, science, and education'' of the Herzen State Pedagogical University of Russia.

Author information

Authors and Affiliations

  1. Herzen State Pedagogical University of Russia, 48 Moyka River Embankment, Saint Petersburg, 191186, Russia

    Vasilii V. Pelipko, Ruslan I. Baichurin & Sergey V. Makarenko

  2. Lomonosov Moscow State University, 1, Build 3 Leninskie Gory, Moscow, 119991, Russia

    Konstantin A. Lyssenko

Authors
  1. Vasilii V. Pelipko
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Ruslan I. Baichurin
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Konstantin A. Lyssenko
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Sergey V. Makarenko
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Sergey V. Makarenko.

Additional information

Translated from Khimiya Geterotsiklicheskikh Soedinenii, 2023, 59(4/5), 322–326

Supplementary Information

Below is the link to the electronic supplementary material.

Supplementary file1 (PDF 2638 kb)

Rights and permissions

Springer Nature or its licensor (e.g. a society or other partner) holds exclusive rights to this article under a publishing agreement with the author(s) or other rightsholder(s); author self-archiving of the accepted manuscript version of this article is solely governed by the terms of such publishing agreement and applicable law.

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Pelipko, V.V., Baichurin, R.I., Lyssenko, K.A. et al. Nitromethylidene-containing piperazinones and morpholinone: synthesis and structure. Chem Heterocycl Comp 59, 322–326 (2023). https://doi.org/10.1007/s10593-023-03200-3

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s10593-023-03200-3

Keywords

Search

Navigation