Skip to main content
Log in

3-Nitroacrylates as promising substrates for the construction of carbo- and heterocyclic structures

  • Reviews
  • Published:
Russian Chemical Bulletin Aims and scope

Abstract

The review analyzes and summarizes methods for the synthesis of carbo- and heterocycles based on alkyl 3-nitroacrylates that were described over the past decade. The scope of the review includes cycloaddition reactions and tandem processes, in particular Michael-initiated ring closure (MIRC) reactions, giving functionalized carbo- and heterocycles, mainly five- and six-membered derivatives.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Similar content being viewed by others

References

  1. V. M. Berestovitskaya, S. V. Makarenko, K. D. Sadikov, A. S. Smirnov, Izv. Ros. Gos. Ped. Un-ta im. A. I. Gertsena [IZVESTIA: Herzen University J. Humanities Sci.], 2007, No. 8(38), 59 (in Russian).

  2. S. V. Makarenko, K. D. Sadikov, A. S. Smirnov, V. M. Berestovitskaya, Izv. Ros. Gos. Ped. Un-ta im. A. I. Gertsena [IZVESTIA: Herzen University J. Humanities Sci.], 2009, No. 95, 169 (in Russian).

  3. R. Ballini, S. Gabrielli, A. Palmieri, Curr. Org. Chem., 2010, 14, 65.

    Article  CAS  Google Scholar 

  4. S. Gabrielli, E. Chiurchiù, A. Palmieri, Adv. Synth. Catal., 2019, 361, 630.

    Article  CAS  Google Scholar 

  5. S. Umemiya, Y. Hayashi, Eur. J. Org. Chem., 2015, 4320.

  6. R. Porta, M. Benaglia, F. Coccia, F. Cozzi, A. Puglisi, Adv. Synth. Catal., 2015, 357, 377.

    Article  CAS  Google Scholar 

  7. E. Massolo, S. Palmieri, M. Benaglia, V. Capriati, F. M. Perna, Green Chem., 2016, 18, 792.

    Article  CAS  Google Scholar 

  8. Z. Chen, Y. Zheng, J. A. Ma, Angew. Chem., 2017, 129, 4640.

    Article  Google Scholar 

  9. Z. Chen, Y. Zhang, J. Nie, J. A. Ma, Org. Lett., 2018, 20, 2120.

    Article  CAS  Google Scholar 

  10. R. Jasiński, K. Mróz, A. Kącka, J. Heterocycl. Chem., 2016, 53, 1424.

    Article  Google Scholar 

  11. M. K. Leibowitz, E. S. Winter, J. R. Scheerer, Tetrahedron Lett., 2015, 56, 6069.

    Article  CAS  Google Scholar 

  12. V. V. Pelipko, S. V. Makarenko, V. M. Berestovitskaya, R. I. Baichurin, Chem. Heterocycl. Compd., 2016, 52, 574.

    Article  CAS  Google Scholar 

  13. V. V. Pelipko, R. I. Baichurin, R. P. Kustin, A. P. Vinogradov, S. V. Makarenko, Chem. Heterocycl. Compd., 2018, 54, 729.

    Article  CAS  Google Scholar 

  14. S. Biswas, A. Dagar, A. Srivastava, S. Samanta, Eur. J. Org. Chem., 2015, 4493.

  15. S. Gabrielli, A. Giardinieri, S. Sampaolesi, R. Ballini, A. Palmieri, Molecules, 2016, 21, 776.

    Article  Google Scholar 

  16. V. V. Pelipko, S. V. Makarenko, R. I. Baichurin, V. M. Berestovitskaya, K. S. Kovalenko, Russ. J. Org. Chem., 2017, 53, 1799.

    Article  CAS  Google Scholar 

  17. R. G. Pritchard, R. J. Stoodley, W. H. Yuen, Org. Biomol. Chem., 2005, 3, 162.

    Article  CAS  Google Scholar 

  18. J. F. Schneider, M. B. Lauber, V. Muhr, D. Kratzer, J. Paradies, Org. Biomol. Chem., 2011, 9, 4323.

    Article  CAS  Google Scholar 

  19. N. J. Martin, X. Cheng, B. List, J. Am. Chem. Soc., 2008, 130, 13862.

    Article  CAS  Google Scholar 

  20. S. Li, T. Xiao, D. Li, X. Zhang, Org. Lett., 2015, 17, 3782.

    Article  CAS  Google Scholar 

  21. L. A. Chen, X. Tang, J. Xi, W. Xu, L. Gong, E. Meggers, Angew. Chem., Int. Ed., 2013, 52, 14021.

    Article  CAS  Google Scholar 

  22. J. Q. Weng, Q. M. Deng, L. Wu, K. Xu, H. Wu, R. R. Liu, J. R. Gao, Y. X. Jia, Org. Lett., 2014, 16, 776.

    Article  CAS  Google Scholar 

  23. M. Yoshida, E. Masaki, H. Ikehara, S. Hara, Org. Biomol. Chem., 2012, 10, 5289.

    Article  CAS  Google Scholar 

  24. I. Jovel, S. Prateeptongkum, R. Jackstell, N. Vogl, C. Weckbecker, M. Beller, Adv. Synth. Catal., 2008, 350, 2493.

    Article  CAS  Google Scholar 

  25. Y. A. Volkova, E. B. Averina, Y. K. Grishin, V. B. Rybakov, T. S. Kuznetsova, N. S. Zefirov, Tetrahedron Lett., 2011, 52, 2910.

    Article  CAS  Google Scholar 

  26. WO Pat. 2017/133657; https://doi.org/worldwide.espacenet.com.

  27. N. A. Anisimova, A. A. Kuzhaeva, G. A. Berkova, V. M. Berestovitskaya, Russ. J. Gen. Chem., 2011, 81, 1845.

    Article  CAS  Google Scholar 

  28. F. D. Boyer, X. Le Goff, I. Hanna, J. Org. Chem., 2008, 73, 5163.

    Article  CAS  Google Scholar 

  29. F. D. Boyer, I. Hanna, Eur. J. Org. Chem., 2008, 4938.

  30. F. D. Boyer, J. Dubois, S. Thoret, M. E. T. H. Dau, I. Hanna, Bioorg. Chem., 2010, 38, 149.

    Article  CAS  Google Scholar 

  31. S. Mukherjee, E. J. Corey, Org. Lett., 2010, 12, 1024.

    Article  CAS  Google Scholar 

  32. US Pat. 2014/256976; https://doi.org/worldwide.espacenet.com.

  33. M. Calmes, F. Escale, C. Didierjean, J. Martinez, Chirality, 2011, 23, 245.

    Article  CAS  Google Scholar 

  34. N. A. Anisimova, A. A. Kuzhaeva, G. A. Berkova, V. M. Berestovitskaya, Russ. J. Gen. Chem., 2012, 82, 2013.

    Article  CAS  Google Scholar 

  35. T. K. Behera, S. N. Islam, S. M. Mobin, V. Singh, Tetrahedron Lett., 2014, 55, 5170.

    Article  CAS  Google Scholar 

  36. N. A. Anisimova, V. M. Berestovitskaya, I. S. Bagryanskaya, M. E. Ivanova, G. A. Berkova, A. A. Kuzhaeva, Russ. J. Gen. Chem., 2010, 80, 308.

    Article  CAS  Google Scholar 

  37. H. Jiang, C. Rodríguez-Escrich, T. K. Johansen, R. L. Davis, K. A. Jørgensen, Angew. Chem., 2012, 124, 10417.

    Article  Google Scholar 

  38. E. Massolo, M. Benaglia, D. Parravicini, D. Brenna, R. Annunziata, Tetrahedron Lett., 2014, 55, 6639.

    Article  CAS  Google Scholar 

  39. S. Gabrielli, A. Palmieri, D. S. Panmand, D. Lanari, L. Vaccaro, R. Ballini, Tetrahedron, 2012, 68, 8231.

    Article  CAS  Google Scholar 

  40. H. Ishikawa, T. Suzuki, Y. Hayashi, Angew. Chem., 2009, 121, 1330.

    Article  Google Scholar 

  41. H. Ishikawa, B. P. Bondzic, Y. Hayashi, Eur. J. Org. Chem., 2011, 6020.

  42. H. Shen, K. F. Yang, Z. H. Shi, J. X. Jiang, G. Q. Lai, L. W. Xu, Eur. J. Org. Chem., 2011, 5031.

  43. CN Pat. 105461629; https://doi.org/worldwide.espacenet.com.

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

    Article  CAS  Google Scholar 

  45. N. Guttenberger, T. Schlatzer, M. Leypold, S. Tassoti, R. Breinbauer, Monatsh. Chem., 2018, 149, 847.

    Article  CAS  Google Scholar 

  46. A. Manabe, Y. Ohfune, T. Shinada, Tetrahedron Lett., 2014, 55, 6077.

    Article  CAS  Google Scholar 

  47. V. M. Berestovitskaya, N. A. Anisimova, O. N. Kataeva, G. A. Berkova, A. Jager, Russ. J. Gen. Chem., 2008, 78, 954.

    Article  CAS  Google Scholar 

  48. R. Ballini, S. Gabrielli, A. Palmieri, Synlett, 2009, 965.

  49. R. Ballini, A. Palmieri, M. A. Talaq, S. Gabrielli, Adv. Synth. Catal., 2009, 351, 2611.

    Article  CAS  Google Scholar 

  50. T. Kano, A. Yamamoto, S. Song, K. Maruoka, Bull. Chem. Soc. Jpn, 2011, 84, 1057.

    Article  CAS  Google Scholar 

  51. R. Ballini, S. Gabrielli, A. Palmieri, Synlett, 2010, 2468.

  52. A. Palmieri, S. Gabrielli, C. Cimarelli, R. Ballini, Green Chem., 2011, 13, 3333.

    Article  CAS  Google Scholar 

  53. A. Palmieri, S. Gabrielli, R. Maggi, R. Ballini, Synlett, 2014, 25, 128.

    Article  CAS  Google Scholar 

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

    Article  CAS  Google Scholar 

  55. H. Ishikawa, S. Sawano, Y. Yasui, Y. Shibata, Y. Hayashi, Angew. Chem., 2011, 123, 3858.

    Article  Google Scholar 

  56. G. S. Kumar, S. P. Ragini, H. M. Meshram, Tetrahedron Lett., 2013, 54, 5974.

    Article  Google Scholar 

  57. S. Gabrielli, R. Ballini, A. Palmieri, Monatsh. Chem., 2013, 144, 509.

    Article  CAS  Google Scholar 

  58. L. N. Gautam, Q. Wang, N. G. Akhmedov, J. L. Petersen, X. Shi, Org. Biomol. Chem., 2013, 11, 1917.

    Article  CAS  Google Scholar 

  59. B. M. Babu, G. S. Kumar, P. B. Thakur, V. M. Bangade, H. M. Meshram, Tetrahedron Lett., 2014, 55, 3473.

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to S. V. Makarenko.

Additional information

Dedicated to the 60th anniversary of the Problem Laboratory of Nitro Compounds of the Herzen State Pedagogical University of Russia.

Not only alkyl 3-nitropropenoates but also homologous alkyl 3-nitroalk-2-enoates are regarded as nitroacrylates in the literature.

Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 10, pp. 1821–1837, October, 2019.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Pelipko, V.V., Baichurin, R.I. & Makarenko, S.V. 3-Nitroacrylates as promising substrates for the construction of carbo- and heterocyclic structures. Russ Chem Bull 68, 1821–1837 (2019). https://doi.org/10.1007/s11172-019-2631-z

Download citation

  • Received:

  • Revised:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11172-019-2631-z

Key words

Navigation