Skip to main content
SpringerLink
Log in

Alkyl 3-nitroacrylates: Synthesis and reactions with cyclohexane-1,3-diones and Meldrum’s acid

  • Published:
Russian Journal of Organic Chemistry Aims and scope Submit manuscript

Abstract

A modified procedure was proposed for the synthesis of alkyl 3-nitroacrylates by nitroiodination of alkyl acrylates and subsequent dehydroiodination of iodonitropropanoates with triethylamine. Alkyl 3-nitroacrylates reacted with cyclohexane-1,3-dione, dimedone, and Meldrum’s acid in the presence of N,N,N-tri-methylanilinium hydroxide (Rodionov’s catalyst) in anhydrous methanol to give the corresponding Michael adducts.

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. Palmieri, A., Gabrielli, S., and Ballini, R., Green Chem., 2013, vol. 15, p. 2344.

    Article  CAS  Google Scholar 

  2. Ballini, R., Gabrielli, S., and Palmieri, A., Curr. Org. Chem., 2010, vol. 14, p. 65.

    Article  CAS  Google Scholar 

  3. Makarenko, S.V., Sadikov, K.D., Smirnov, A.S., and Berestovitskaya, V.M., Izv. Ross. Gos. Ped. Univ. im. A.I. Gertsena, 2009, no. 95, p. 169.

    Google Scholar 

  4. Anderson, J.C., Horsfall, L.R., Kalogirou, A.S., Mills, M.R., Stepney, G.J., and Tizzard, G.J., J. Org. Chem., 2012, vol. 77, p. 6186.

    Article  CAS  Google Scholar 

  5. Anderson, J.C., Kalogirou, A.S., and Tizzard, G.J., Tetrahedron, 2014, vol. 70, p. 9337.

    Article  CAS  Google Scholar 

  6. Pelipko, V.V., Makarenko, S.V., Berestovitskaya, V.M., and Baichurin, R.I., Chem. Heterocycl. Compd., 2016, vol. 52, p. 574.

    Article  CAS  Google Scholar 

  7. Petri, A., Seidelmann, O., Eilitz, U., Leßmann, F., Reißmann, S., Wendisch, V., and Gutnov, A., Tetrahedron Lett., 2014, vol. 55, p. 267.

    Article  CAS  Google Scholar 

  8. Ganesh, M. and Seidel, D., J. Am. Chem. Soc., 2008, vol. 130, p. 16 464.

    Article  CAS  Google Scholar 

  9. Trost, B.M. and Müller, C., J. Am. Chem. Soc., 2008, vol. 130, p. 2438.

    Article  CAS  Google Scholar 

  10. Zhu, S., Yu, S., and Ma, D., Angew. Chem., Int. Ed., 2008, vol. 47, p. 545.

    Article  CAS  Google Scholar 

  11. Austin, R.E., Maplestone, R.A., Sefler, A.M., Liu, K., Hruzewicz, W.N., Liu, C.W., Cho, H.S., Wemmer, D.E., and Bartlett, P.A., J. Am. Chem. Soc., 1997, vol. 119, p. 6461.

    Article  CAS  Google Scholar 

  12. Bunnage, M.E., Ganesh, T., Masesane, I.B., Orton, D., and Steel, P.G., Org. Lett., 2003, vol. 5, p. 239.

    Article  CAS  Google Scholar 

  13. Rimkus, A. and Sewald, N., Org. Lett., 2003, vol. 5, p. 79.

    Article  CAS  Google Scholar 

  14. Cheng, R.P., Gellman, S.H., and DeGrado, W.F., Chem. Rev., 2001, vol. 101, p. 3219.

    Article  CAS  Google Scholar 

  15. Berestovitskaya, V.M., Makarenko, S.V., Sadikov, K.D., and Smirnov, A.S., Izv. Ross. Gos. Ped. Univ. im. A.I. Gertsena, 2007, no. 38, p. 59.

    Google Scholar 

  16. Banfi, L., Basso, A., Chiappe, C., De Moliner, F., Riva, R., and Sonaglia, L., Org. Biomol. Chem., 2012, vol. 10, p. 3819.

    Article  CAS  Google Scholar 

  17. Ballini, R., Fiorini, D., and Palmieri, A., Tetrahedron Lett., 2004, vol. 45, p. 7027.

    Article  CAS  Google Scholar 

  18. Bwire, R.N., Majinda, R.R., Masesane, I.B., and Steel, G.S., Pure Appl. Chem., 2009, vol. 81, p. 105.

    Article  CAS  Google Scholar 

  19. Itoh, K., Kitoh, K., and Kishimoto, S., Can. J. Chem., 2006, vol. 84, p. 392.

    Article  CAS  Google Scholar 

  20. Masesane, I.B., Batsanov, A.S., Howard, J.A.K., Mondal, R., and Steel, P.G., Beilstein J. Org. Chem., 2006, vol. 2, p. 9.

    Article  Google Scholar 

  21. McMurry, J.E., Musser, J.H., Fleming, I., Fortunak, J., and Nübling, C., Org. Synth., 1977, vol. 56, p. 65.

    Article  CAS  Google Scholar 

  22. Pritchard, R.G., Stoodley, R.J., and Yuen, W.-H., Org. Biomol. Chem., 2005, vol. 3, p. 162.

    Article  CAS  Google Scholar 

  23. Gawinecki, R., Kolehmainen, E., Dobosz, R., Khouzani, H.L., and Chandrasekaran, S., J. Iran. Chem. Soc., 2014, vol. 11, p. 17.

    Article  CAS  Google Scholar 

  24. Kozerski, L. and Krówczyński, A., Magn. Reson. Chem., 1987, vol. 25, p. 46.

    Article  CAS  Google Scholar 

  25. Rajappa, S., Nagarajan, K., Venkatesan, K., Kamath, N., Padmanabhan, V.M., von Philipsborn, W., Chen, B.C., and Müller, R., Helv. Chim. Acta, 1984, vol. 67, p. 1669.

    Article  CAS  Google Scholar 

  26. Neiland, O.Ya., Tsiklicheskie β-diketony (Cyclic β-Diketones), Vanag, G., Ed., Riga: Akad. Nauk Latv. SSR, 1961, p. 41.

    Google Scholar 

  27. Trukhin, E.V., Sheremet, E.A., and Berestovitskaya, V.M., Russ. Chem. Bull., Int. Ed., 2009, vol. 58, p. 2035.

    Article  CAS  Google Scholar 

  28. Berestovitskaya, V.M., Baichurin, R.I., Baichurina, L.V., Fel’gendler, A.V., and Aboskalova, N.I., Russ. J. Gen. Chem., 2013, vol. 83, p. 1755.

    Article  CAS  Google Scholar 

  29. Kazitsyna, L.A. and Kupletskaya, N.B., Primenenie UF-, IK-, YaMR- i mass spektroskopii v organicheskoi khimii (Application of UV, IR, NMR, and Mass Spectroscopy in Organic Chemistry), Moscow: Mosk. Gos. Univ., 1979.

    Google Scholar 

  30. D’Oca, C.R.M., Naciuk, F.F., Silva, J.C., Guedes, E.P., Moro, C.C., D’Oca, M.G.M., Santos, L.S., Natchigall, F.M., and Russowsky, D., J. Braz. Chem. Soc., 2017, vol. 28, p. 285.

    Google Scholar 

  31. Li, J.-H., Li, Z.-G., and Chen, Q.-G., J. Chem. Res., 2004, p. 758.

    Google Scholar 

  32. Zia-Ebrahimi, M. and Huffman, G.W., Synthesis, 1996, p. 215.

    Google Scholar 

  33. Baron, M., Métay, E., Lemaire, M., and Popowycz, F., J. Org. Chem., 2012, vol. 77, p. 3598.

    Article  CAS  Google Scholar 

  34. Kataja, A.O. and Koskinen, A.M.P., Arkivoc, 2010, part (ii), p. 205.

    Google Scholar 

  35. Martin, G.J., Martin, M.L., and Gouesnard, J.-P., 15N NMR Spectroscopy, Berlin: Springer, 1981.

    Book  Google Scholar 

  36. Klapötke, T.M., Krumm, B., and Moll, R., Chem. Eur. J., 2013, vol. 19, p. 12 113.

    Article  Google Scholar 

  37. Rodionov, V.M. and Yartseva, N.G., Izv. Akad. Nauk SSSR, Otd. Khim. Nauk, 1948, p. 251.

    Google Scholar 

  38. Tietze, L.F., Eicher, T., Diederichsen, U., Speicher, A., and Schützenmeister, N., Reactions and Syntheses: In the Organic Chemistry Laboratory, Weinheim: Wiley–VCH, 2014, 2nd ed. Translated under the title Preparativnaya organicheskaya khimiya: Reaktsii i sintezy v praktikume organicheskoi khimii i nauchno-issledovatel’skoi laboratorii, Moscow: Mir, 2015, p. 157.

    Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Herzen State Pedagogical University of Russia, nab. r. Moiki 48, St. Petersburg, 191186, Russia

    V. V. Pelipko, S. V. Makarenko, R. I. Baichurin & V. M. Berestovitskaya

  2. Chemical and Food Fragrances Factory Ltd., ul. Partizanskaya 11, St. Petersburg, 195027, Russia

    K. S. Kovalenko

Authors
  1. V. V. Pelipko
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. S. V. Makarenko
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. R. I. Baichurin
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. V. M. Berestovitskaya
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. K. S. Kovalenko
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to S. V. Makarenko.

Additional information

Original Russian Text © V.V. Pelipko, S.V. Makarenko, R.I. Baichurin, V.M. Berestovitskaya, K.S. Kovalenko, 2017, published in Zhurnal Organicheskoi Khimii, 2017, Vol. 53, No. 12, pp. 1765–1773.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Pelipko, V.V., Makarenko, S.V., Baichurin, R.I. et al. Alkyl 3-nitroacrylates: Synthesis and reactions with cyclohexane-1,3-diones and Meldrum’s acid. Russ J Org Chem 53, 1799–1808 (2017). https://doi.org/10.1134/S107042801712003X

Download citation

  • Received:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1134/S107042801712003X

Search

Navigation