Skip to main content
SpringerLink
Log in

Recent advances in the synthesis and reactivity of spiro-epoxyoxindoles

  • Published:
Chemistry of Heterocyclic Compounds Aims and scope

Spiro-epoxyoxindoles containing an unsubstituted methylene fragment in the oxirane ring are excellent building blocks in organic synthesis due to the high reactivity conferred by the three-membered oxygenated cycle. In this minireview, a concise survey of the methods of their synthesis and examples of reactivity with carbon and nitrogen nucleophiles is presented, with a particular focus on the stereochemical aspects. The review covers the literature for the last twenty years.

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.
Scheme 1.
Scheme 2.
Scheme 3.
Scheme 4.
Scheme 5.
Scheme 6.
Scheme 7.
Scheme 8.
Scheme 9.

Similar content being viewed by others

References

  1. Singh, G. S.; Desta, Z. Y. Chem. Rev. 2012, 112, 6104.

    Article  CAS  PubMed  Google Scholar 

  2. Rios, R. Chem. Soc. Rev. 2012, 41, 1060.

    Article  CAS  PubMed  Google Scholar 

  3. Schulz, V.; Davoust, M.; Lemarié, M.; Lohier, J.-F.; Sopkova de Oliveira Santos, J.; Metzner, P.; Brière, J.-F. Org. Lett. 2007, 9, 1745.

  4. Mamuye, A. D.; Monticelli, S.; Castoldi, L.; Holzer, W.; Pace, V. Green Chem. 2015, 17, 4194.

    Article  CAS  Google Scholar 

  5. (a) Arndt, F.; Eistert, B.; Ender, W. Chem. Ber. 1929, 62, 44. (b) Pace, V.; Verniest, G.; Sinisterra, J.-V.; Alcántara, A. R.; De Kimpe, N. J. Org. Chem. 2010, 75, 5760.

  6. Alcaide, B.; Almendros, P.; Aragoncillo, C.; Gómez-Campillos, G.; Arnó, M.; Domingo, L. R. ChemPlusChem 2012, 77, 563.

    Article  CAS  Google Scholar 

  7. Chodnekar, M. S.; Crowther, A. F.; Hepworth, W.; Howe, R.; McLoughlin, B. J.; Mitchell, A.; Rao, B. S.; Slatcher, R. P.; Smith, L. H.; Stevens, M. A. J. Med. Chem. 1972, 15, 49.

    Article  CAS  PubMed  Google Scholar 

  8. (a) Chouhan, M.; Senwar, K. R.; Sharma, R.; Grover, V.; Nair, V. A. Green Chem. 2011, 13, 2553. (b) Kumar, K.; Konar, D.; Goyal, S.; Gangar, M.; Chouhan, M.; Rawal, R. K.; Nair, V. A. J. Org. Chem. 2016, 81, 9757.

  9. (a) Hajra, S.; Maity, S.; Maity, R. Org. Lett. 2015, 17, 3430. (b) Hajra, S.; Maity, S.; Roy, S. Adv. Synth. Catal. 2016, 358, 2300.

  10. Lou, M.-M.; Wang, H.; Song, L.; Liu, H.-Y.; Li, Z.-Q.; Guo, X.-S.; Zhang, F.-G.; Wang, B. J. Org. Chem. 2016, 81, 5915.

    Article  CAS  PubMed  Google Scholar 

  11. Gorokhovik, I.; Neuville, L.; Zhu, J. Org. Lett. 2011, 13, 5536.

    Article  CAS  PubMed  Google Scholar 

  12. (a) Pace, V.; Castoldi, L.; Mazzeo, E.; Rui, M.; Langer, T.; Holzer, W. Angew. Chem., Int. Ed. 2017, 56, 12677. (b) Pace, V.; Holzer, W.; De Kimpe, N. Chem. Rec. 2016, 16, 2061. (c) Pace, V.; Castoldi, L.; Holzer, W. Adv. Synth. Catal. 2014, 356, 1761. (d) Pace, V. Aust. J. Chem. 2014, 67, 311. (e) Castoldi, L.; Monticelli, S.; Senatore, R.; Ielo, L.; Pace, V. Chem. Commun. 2018. DOI: https://doi.org/10.1039/C8CC02499E.

  13. (a) Pace, V.; Castoldi, L.; Mamuye, A. D.; Langer, T.; Holzer, W. Adv. Synth. Catal. 2016, 358, 172. (b) Pace, V.; Castoldi, L.; Monticelli, S.; Rui, M.; Collina, S. Synlett 2017, 879.

  14. Pace, V.; Holzer, W.; Verniest, G.; Alcántara, A. R.; De Kimpe, N. Adv. Synth. Catal. 2013, 355, 919.

  15. Zhang, B.; Li, Y.; Bao, G.; Zhu, G.; Li, J.; Wang, J.; Zhang, B.; Sun, W.; Hong, L.; Wang, R. Green Chem. 2017, 19, 2107.

    Article  CAS  Google Scholar 

  16. Hajra, S.; Roy, S. S.; Aziz, S. M.; Das, D. Org. Lett. 2017, 19, 4082.

    Article  CAS  PubMed  Google Scholar 

  17. Luo, M.; Yuan, R.; Liu, X.; Yu, L.; Wei, W. Chem.–Eur. J. 2016, 22, 9797.

    Article  CAS  PubMed  Google Scholar 

  18. Zhu, G.; Bao, G.; Li, Y.; Sun, W.; Li, J.; Hong, L.; Wang, R. Angew. Chem., Int. Ed. 2017, 56, 5332.

  19. Zhu, G.; Li, Y.; Bao, G.; Sun, W.; Huang, L.; Hong, L.; Wang, R. ACS Catal. 2018, 8, 1810.

    Article  CAS  Google Scholar 

  20. Hajra, S.; Roy, S.; Maity, S. Org. Lett. 2017, 19, 1998.

    Article  CAS  PubMed  Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Department of Pharmaceutical Chemistry, University of Vienna, 14 Althanstrasse, 1090, Vienna, Austria

    Serena Monticelli, Laura Castoldi, Saad Touqeer, Margherita Miele, Ernst Urban & Vittorio Pace

Authors
  1. Serena Monticelli
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Laura Castoldi
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Saad Touqeer
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Margherita Miele
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. Ernst Urban
    View author publications

    You can also search for this author in PubMed Google Scholar

  6. Vittorio Pace
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Vittorio Pace.

Additional information

Published in Khimiya Geterotsiklicheskikh Soedinenii, 2018, 54(0), 389–393

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Monticelli, S., Castoldi, L., Touqeer, S. et al. Recent advances in the synthesis and reactivity of spiro-epoxyoxindoles. Chem Heterocycl Comp 54, 389–393 (2018). https://doi.org/10.1007/s10593-018-2280-4

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s10593-018-2280-4

Keywords

Search

Navigation