Skip to main content
SpringerLink
Log in

Cycloaddition reactions in the synthesis of isoindolines (microreview)

  • HETEROCYCLES IN FOCUS
  • Published:
Chemistry of Heterocyclic Compounds Aims and scope

A summary of the most recent approaches toward isoindoline derivatives via cycloaddition reaction is discussed. The microreview covers the latest selected examples (2010–2017) on the synthesis of isoindolines that are divided into several distinct categories depending on the structure of the starting compound – intramolecular [3+2] cycloaddition of azides, [3+2] cycloaddition of azomethine ylides, [2+2+2] cycloadditions, and others.

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. (a) Sović, I.; Karminski-Zamola, G. Kem. Ind. 2014, 63, 173. (b) Sović, I.; Karminski-Zamola, G. Kem. Ind. 2014, 63, 183.

  2. Speck, K.; Magauer, T. Beilstein J. Org. Chem., 2013, 9, 2048.

    Article  Google Scholar 

  3. Watson, T. J.; Ayers, T. A.; Shah, N.; Wenstrup, D.; Webster, M.; Freund, D.; Horgan, S.; Carey, J. P. Org. Process Res. Dev. 2003, 7, 521.

    Article  CAS  Google Scholar 

  4. Xie, Y.-Y.; Wang, Y.-Ch.; He, Y.; Hu, D.-Ch.; Wang, H.-Sh.; Pan, Y.-M. Green Chem. 2017, 19, 656.

    Article  CAS  Google Scholar 

  5. Starosotnikov, A. M.; Bastrakov, M. A.; Pechenkin, S. Yu.; Leontieva, M. A.; Kachala, V. V.; Shevelev, S. A. J. Heterocycl. Chem. 2011, 48, 824.

    Article  CAS  Google Scholar 

  6. Bastrakov, M. A.; Leonov, A. I.; Starosotnikov, A. M.; Fedyanin, I. V.; Shevelev, S. A. Russ. Chem. Bull., Int. Ed. 2013, 62, 1052. [Izv. Akad. Nauk, Ser. Khim., 2013, 62, 1051.]

  7. Bastrakov, M. A.; Starosotnikov, A. M.; Kachala, V. V.; Fedyanin, I. V.; Shevelev, S. A. Asian J. Org. Chem. 2015, 4, 146.

    Article  CAS  Google Scholar 

  8. Starosotnikov, A. M.; Bastrakov, M. A.; Kachala, V. V.; Belyakov, P. A.; Fedyanin, I. V.; Shevelev, S. A. Synlett 2012, 2400.

  9. Wang, Ch.; Chen, X.-H.; Zhou, Sh.-M.; Gong, L.-Zh. Chem. Commun. 2010, 46, 1275

    Article  CAS  Google Scholar 

  10. He, Zh.; Liu, T.; Tao, H.; Wang, Ch.-J. Org. Lett. 2012, 14, 6230.

    Article  CAS  Google Scholar 

  11. He, Zh.; Liu, T.; Tao, H.; Wang, Ch.-J. Org. Lett. 2014, 16, 5506.

    Article  CAS  Google Scholar 

  12. Clary, K. N.; Parvez, M.; Back, T. J. J. Org. Chem. 2010, 75, 3751.

    Article  CAS  Google Scholar 

  13. Zhu, Sh.; Cao, J.; Wu, L.; Huang, X. J. Org. Chem. 2012, 77, 10409.

    Article  CAS  Google Scholar 

  14. Auvinet, A.-L.; Ez-Zoubir, M.; Vitale, M. R.; Brown, J. A.; Michelet, V.; Ratovelomanana-Vidal, V. ChemSusChem 2012, 5, 1888.

    Article  CAS  Google Scholar 

  15. Auvinet, A.-L.; Ez-Zoubir, M.; Bompard, S.; Vitale, M. R.; Brown, J. A.; Michelet, V.; Ratovelomanana-Vidal, V. ChemCatChem 2013, 5, 2389.

    Article  CAS  Google Scholar 

  16. Jacquet, J.; Auvinet, A.-L.; Mandadapu, A. K.; Haddad, M.; Ratovelomanana-Vidal, V.; Michelet, V. Adv. Synth. Catal. 2015, 357, 1387.

    Article  CAS  Google Scholar 

  17. Auvinet, A.-L.; Michelet, V.; Ratovelomanana-Vidal, V. Synthesis 2013, 2003.

  18. Liang, C.; Gu, L.; Yang, Y.; Chen, X. Synth. Commun. 2014, 44, 2416.

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

  1. N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky Ave, Moscow, 119991, Russia

    Alexey M. Starosotnikov & Maxim A. Bastrakov

Authors
  1. Alexey M. Starosotnikov
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Maxim A. Bastrakov
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding authors

Correspondence to Alexey M. Starosotnikov or Maxim A. Bastrakov.

Additional information

Published in Khimiya Geterotsiklicheskikh Soedinenii, 2017, 53(11), 1181–1183

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Starosotnikov, A.M., Bastrakov, M.A. Cycloaddition reactions in the synthesis of isoindolines (microreview). Chem Heterocycl Comp 53, 1181–1183 (2017). https://doi.org/10.1007/s10593-018-2191-4

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s10593-018-2191-4

Keywords

Search

Navigation