Skip to main content
SpringerLink
Log in

The Diels–Alder reaction in the synthesis of fused heterocyclic aromatic compounds

  • Published:
Chemistry of Heterocyclic Compounds Aims and scope

The review summarizes data on the synthesis of fused heterocyclic aromatic compounds by the Diels–Alder reaction, including as part of cascade reactions, and the dehydro-Diels–Alder reaction published over the past five years. In all the examples presented, the Diels–Alder reaction was used to assemble the polycyclic core of the considered molecules.

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. Stępień, M.; Gońka, E.; Żyła, M.; Sprutta, N. Chem. Rev. 2017, 117, 3479.

    Article  PubMed  Google Scholar 

  2. Zhao, X.; Chaudhry, S. T.; Mei, J. Adv. Heterocycl. Chem. 2017, 121, 133.

    Article  CAS  Google Scholar 

  3. Kondratov, I. S.; Tolmachova, N. A.; Haufe, G. Eur. J. Org. Chem. 2018, 3618.

  4. Dyan, O. T.; Borodkin, G. I.; Zaikin, P. A. Eur. J. Org. Chem. 2019, 7271.

  5. Yu, F.; Li, D.; Wei, Y.; Kang, R. M.; Guo, Q. X. Tetrahedron 2018, 74, 1965.

    Google Scholar 

  6. Fang, R.-J.; Yan, C.; Sun, J.; Han, Y.; Yan, C.-G. Beilstein J. Org. Chem. 2021, 17, 2425.

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  7. Gulbrandsen, H. S.; Serigstad, H.; Lovell Read, M.; Joos, I.; Gundersen, L.-L. Eur. J. Org. Chem. 2019, 6044.

  8. Manikandan, P.; Karunakaran, J.; Varathan, E.; Schreckenbach, G.; Mohanakrishnan, A. K. Chem. Commun. 2020, 56, 15317.

    Article  CAS  Google Scholar 

  9. Zhang, Z.; Zhang, Q. Mater. Chem. Front. 2020, 4, 3419.

    Article  CAS  Google Scholar 

  10. Chou, T.-C.; Cheng, J.-F.; Gholap, A. R.; Huang, J. J.-K.; Chen, J.-C.; Huang, J.-K.; Tseng, J.-C. Tetrahedron 2019, 75, 130689.

    Article  Google Scholar 

  11. Zhang, P.-F.; Zhuang,-F. D.; Sun, Z.-H.; Lu, Y.; Wang, J.-Y.; Pei, J. J. Org. Chem. 2020, 85, 241.

    Article  CAS  PubMed  Google Scholar 

  12. Kotha, S.; Aswar, V. R.; Chinnam, A. K. Tetrahedron Lett. 2017, 58, 4360.

    Article  CAS  Google Scholar 

  13. Bornadiego, A.; Diáz, J.; Marcos, C. F. J. Org. Chem. 2019, 84, 7426.

    Article  CAS  PubMed  Google Scholar 

  14. Hu, Z.; Dong, J.; Li, Z.; Yuan, B.; Wei, R.; Xu, X. Org. Lett. 2018, 20, 6750.

    Article  CAS  PubMed  Google Scholar 

  15. Sun, X.-S.; Diao, X.-Y.; Dong, X.-Q.; Wang, C.-J. Chem. Sci. 2022, 10448.

  16. Vázquez-Vera, Ó.; Segura-Olvera, D.; Rincón-Guevara, M. A.; Gutiérrez-Carrillo, A.; García-Sánchez, M. A.; Ibarra, I. A.; Lomas-Romero, L.; Islas-Jácome, A.; González-Zamora, E. Molecules 2018, 23, 2029.

    Google Scholar 

  17. Kappe, C. O.; Pieber, B.; Dallinger, D. Angew. Chem., Int. Ed. Engl. 2013, 52, 1088.

  18. Arepalli, S. K.; Park, B.; Jung, J.-K.; Lee, K.; Lee, H. Tetrahedron Lett. 2017, 58, 449.

    Article  CAS  Google Scholar 

  19. Raju, S.; Annamalai, P.; Chen, P.-L.; Liu, Y.-H.; Chuang, S.-C. Chem. Commun. 2017, 53, 6247.

    Article  CAS  Google Scholar 

  20. Talukdar, R.; Singh, V.; Mourya, H.; Nasibullah, M.; Tiwari, B. J. Org. Chem. 2021, 86, 12277.

    Article  CAS  PubMed  Google Scholar 

  21. Wu, F.; Lu, S.; Zhu, S. Adv. Synth. Catal. 2020, 362, 5632.

    Article  CAS  Google Scholar 

  22. Kudoh, T.; Fujisawa, S.; Kitamura, M.; Sakakura, A. Synlett 2017, 2189.

  23. Wang, H.; Wang, S.; Qin, T.; Zi, W. Chem.–Eur. J. 2018, 24, 17911.

  24. Zhang, L.; Jin, T.; Guo, Y.; Martin, A. C.; Sun, K.; Dudley, G. B.; Yang, J. J. Org. Chem. 2021, 86, 16716.

    Article  CAS  PubMed  Google Scholar 

  25. Shibata, T.; Sekine, A.; Mitake, A.; Kanyiva, K. S. Angew. Chem., Int. Ed. 2018, 57, 15862.

  26. Hu, Y.; Ma, J.; Li, L.; Hu, Q.; Lv, S.; Liu, B.; Wang, S. Chem. Commun. 2017, 53, 1542.

    Article  CAS  Google Scholar 

  27. Lee, D.; Ross, S. P.; Xiao, X.; Hoye, T. R. Chem 2021, 7, 2527.

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  28. Jassas, R. S.; Mughal, E. U.; Sadiq, A.; Alsantali, R. I.; Al-Rooqi, M. M.; Naeem, N.; Moussa, Z.; Ahmed, S. A. RSC Adv. 2021, 11, 32158.

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  29. Ammon, F.; Sauer, S. T.; Lippert, R.; Lungerich, D.; Reger, D.; Hampel, F.; Jux, N. Org. Chem. Front. 2017, 4, 861.

    Article  CAS  Google Scholar 

  30. Reger, D.; Haines, P.; Heinemann, F. W.; Guldi, D. M.; Jux, N. Angew. Chem., Int. Ed. 2018, 57, 5938.

  31. Yin, J.; Hu, Y.; Zhang, D.; Li, X.; Jin, W. Tetrahedron 2017, 73, 5794.

    Article  CAS  Google Scholar 

  32. Urieta-Mora, J.; Krug, M.; Wiebke, A.; Perles, J.; Fernández, I.; Molina-Ontoria, A.; Guldi, D. M.; Martín, N. J. Am. Chem. Soc. 2020, 142, 4162.

    Article  CAS  PubMed  Google Scholar 

  33. Shi, Y.; Li, C.; Ma, S.; Zhang, Y. Synthesis 2018, 102.

  34. Dusold, C.; Haines, P.; Platzer, B.; Guldi, D. M.; Hirsch, A. Chem.–Eur. J. 2021, 27, 6511.

  35. Zink-Lorre, N.; Doncel-Giménez, A.; Font-Sanchis, E.; Calbo, J.; Sastre-Santos, Á.; Ortí, E.; Fernández-Lázaro, F. Org. Chem. Front. 2019, 6, 2860.

    Article  CAS  Google Scholar 

  36. Hahn, U.; Maisonhaute, E.; Nierengarten, J. Angew. Chem., Int. Ed. 2018, 57, 10635.

Download references

Author information

Authors and Affiliations

  1. Novosibirsk State University, 2 Pirogova St., Novosibirsk, 630090, Russia

    Ok Ton Dyan

  2. N. N. Vorozhtsov Novosibirsk Institute of Organic Chemistry, Siberian Branch of the Russian Academy of Sciences, 9 Akademika Lavrentieva, Novosibirsk, 630090, Russia

    Ok Ton Dyan & Pavel A. Zaikin

Authors
  1. Ok Ton Dyan
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Pavel A. Zaikin
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Ok Ton Dyan.

Additional information

Translated from Khimiya Geterotsiklicheskikh Soedinenii, 2023, 59(4/5), 201–216

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

Dyan, O.T., Zaikin, P.A. The Diels–Alder reaction in the synthesis of fused heterocyclic aromatic compounds. Chem Heterocycl Comp 59, 201–216 (2023). https://doi.org/10.1007/s10593-023-03183-1

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s10593-023-03183-1

Keywords

Search

Navigation