Skip to main content
Log in

The Ritter reaction for the synthesis of heterocycles

  • REVIEW
  • Published:
Chemistry of Heterocyclic Compounds Aims and scope

This minireview covers the applications of the Ritter reaction for the construction of different aza-heterocycles published in the time frame from 1988 to 2016. During this period, the Ritter reaction was extensively used for the synthesis of oxazolines, imidazolines, isoindolinones, and other heterocycles. The Ritter reaction was also applied in a series of tandem reactions to produce tetrahydropyrans, piperidines, dihydroisoquinolines, and 1-spiro-2,5-cyclohexadienones.

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. Jiang, D.; He, T.; Ma, L.; Wang, Z. RSC Adv. 2014, 4, 64936.

    Article  CAS  Google Scholar 

  2. Bishop, R. Comprehensive Organic Synthesis; Knochel, P.; Molander, G. A., Eds.; Elsevier Ltd.: Oxford, 2014, p. 263.

    Google Scholar 

  3. Umezawa, J.; Takahashi, O.; Furuhashi, K.; Nohira, H. Tetrahedron: Asymmetry 1994, 5, 491.

    Article  CAS  Google Scholar 

  4. Senanayake, C. H.; Roberts, F. E.; DiMichele, L. M.; Ryan, K. M.; Liu, J.; Fredenburgh, L. E.; Foster, B. S.; Douglas, A. W.; Larsen, R. D.; Verhoeven, T. R.; Reider, P. J. Tetrahedron Lett. 1995, 36, 3993.

    Article  CAS  Google Scholar 

  5. Senanayake, C. H.; DiMichele, L. M.; Liu, J.; Fredenburgh, L. E.; Ryan, K. M.; Roberts, F. E.; Larsen, R. D.; Verhoeven, T. R.; Reider, P. J. Tetrahedron Lett. 1995, 36, 7615.

    Article  CAS  Google Scholar 

  6. Davies, I. W.; Senanayake, C. H.; Larsen, R. D.; Verhoeven, T. R.; Reider, P. J. Tetrahedron Lett. 1996, 37, 813.

    Article  CAS  Google Scholar 

  7. Chao, C.-S.; Lin, C.-Y.; Mulani, S.; Hung, W.-C.; Mong, K. T. Chem.–Eur. J. 2011, 17, 12193.

    Article  CAS  Google Scholar 

  8. Rising, T. W. D. F.; Heidecke, C. D.; Moir, J. W. B.; Ling, Z.; Fairbanks, A. J. Chem.–Eur. J. 2008, 14, 6444.

    Article  CAS  Google Scholar 

  9. Gordon, D. M.; Danishefsky, S. J. J. Org. Chem. 1991, 56, 3713.

    Article  CAS  Google Scholar 

  10. Noort, D.; van der Marel, G. A.; Mulder, G. J.; van Boom, J. H. Synlett 1992, 224.

  11. Jiménez Blanco, J. L.; Rubio, E. M.; Ortiz Mellet, C.; García Fernández, J. M. Synlett 2004, 2230.

  12. Vangala, M.; Shinde, G. P. Beilstein J. Org. Chem. 2015, 11, 2289.

    Article  CAS  Google Scholar 

  13. Grammatoglou, K.; Bolsakova, J.; Jirgensons, A. RSC Adv. 2017, 7, 27530.

    Article  CAS  Google Scholar 

  14. Morgan, I. R.; Yazici, A.; Pyne, S. G.; Skelton, B. W. J. Org. Chem. 2008, 73, 2943.

    Article  CAS  Google Scholar 

  15. Wu, P.; Petersen, M. Å.; Petersen, R.; Rasmussen, M. O.; Bonnet, K.; Nielsen, T. E.; Clausen, M. H. Eur. J. Org. Chem. 2015, 5633.

  16. Booker-Milburn, K. I.; Guly, D. J.; Cox, B.; Procopiou, P. A. Org. Lett. 2003, 5, 3313.

    Article  CAS  Google Scholar 

  17. Concellón, J. M.; Riego, E.; Suárez, J. R.; García-Granda, S.; Díaz, M. R. Org. Lett. 2004, 6, 4499.

    Article  Google Scholar 

  18. Li, R.; Jiang, H.; Liu, W.-Y.; Gu, P.-M.; Li, X.-Q. Chin. Chem. Lett. 2014, 25, 583.

    Article  Google Scholar 

  19. Liu, C.; Zhang, Q.; Li, H.; Guo, S.; Xiao, B.; Deng, W.; Liu, L.; He, W. Chem.–Eur. J. 2016, 22, 6208.

    Article  CAS  Google Scholar 

  20. Vshivkova, T. S.; Gorbunov, A. A.; Maiorova, O. A.; Slepukhin, P. A.; Isenov, M. L.; Shklyaev, Y. V. Chem. Heterocycl. Compd. 2016, 52, 58. [Khim. Geterotsikl. Soedin. 2016, 52, 58.]

  21. Van Emelen, K.; Wit, T. D.; Hoornaert, G. J.; Compernolle, F. Org. Lett. 2000, 2, 3083.

    Article  Google Scholar 

  22. Rodriguez, J. B.; Gros, E. G.; Caram, J. A.; Marschoff, C. M. Tetrahedron Lett. 1995, 36, 7825.

    Article  CAS  Google Scholar 

  23. Samaniego, W. N.; Baldessari, A.; Ponce, M. A.; Rodriguez, J. B.; Gros, E. G.; Caram, J. A.; Marschoff, C. M. Tetrahedron Lett. 1994, 35, 6967.

    Article  CAS  Google Scholar 

  24. Ung, A. T.; Williams, S. G.; Angeloski, A.; Ashmore, J.; Kuzhiumparambil, U.; Bhadbhade, M.; Bishop, R. Monatsh. Chem. 2014, 145, 983.

    Article  CAS  Google Scholar 

  25. Bishop, R.; Hawkins, S. C.; Ibana, I. C. J. Org. Chem. 1988, 53, 427.

    Article  CAS  Google Scholar 

  26. Bong, I. C. C.; Ung, A. T.; Craig, D. C.; Scudder, M. L.; Bishop, R. Aust. J. Chem. 1989, 42, 1929.

    Article  CAS  Google Scholar 

  27. Qinghong Lin; Ball, G. E.; Bishop, R. Tetrahedron 1997, 53, 10899.

    Article  CAS  Google Scholar 

  28. Lin, Q; Djaidi, D; Bishop, R.; Craig, D. C.; Scudder, M. L. Aust. J. Chem. 1998, 51, 799.

    Article  CAS  Google Scholar 

  29. Djaidi, D.; Bishop, R.; Craig, D. C.; Scudder, M. L. J. Chem. Soc., Perkin 1 1996, 15, 1859.

    Article  Google Scholar 

  30. Pich, K. C.; Bishop, R.; Craig, D. C.; Scudder, M. L. Aust. J. Chem. 1994, 47, 837.

    Article  CAS  Google Scholar 

  31. Hemtasin, C.; Ung, A. T.; Kanokmedhakul, S.; Kanokmedhakul, K.; Bishop, R.; Satraruji, T.; Bishop, D. Monatsh. Chem. 2012, 143, 955.

    Article  CAS  Google Scholar 

  32. Reddy, U. C.; Rama Raju, B.; Pramod Kumar, E. K.; Saikia, A. K. J. Org. Chem. 2008, 73, 1628.

    Article  CAS  Google Scholar 

  33. Yadav, J. S.; Jayasudhan Reddy, Y.; Adi Narayana Reddy, P.; Subba Reddy, B. V. Org. Lett. 2013, 15, 546.

  34. Subba Reddy, B. V.; Ramesh, K.; Ganesh, A. V.; Narayana Kumar, G. G. K. S.; Yadav, J. S.; Grée, R. Tetrahedron Lett. 2011, 52, 495.

    Article  Google Scholar 

  35. Indukuri, K.; Unnava, R.; Deka, M. J.; Saikia, A. K. J. Org. Chem. 2013, 78, 10629.

    Article  CAS  Google Scholar 

  36. Glushkov, V. A.; Shklyaev, Y. V. Mendeleev Commun. 1998, 8, 17.

    Article  Google Scholar 

  37. Glushkov, V. A.; Ausheva, O. G.; Postanogova, G. A.; Shklyaev, Y. V. Chem. Heterocycl. Compd. 2000, 36, 1344. [Khim. Geterotsikl. Soedin. 2000, 1559.]

  38. Glushkov, V. A.; Ausheva, O. G.; Shurov, S. N.; Shklyaev, Y. V. Russ. Chem. Bull., Int. Ed. 2002, 51, 894. [Izv. Akad. Nauk, Ser. Khim. 2002, 822.]

  39. Plekhanova, I. V.; Stryapunina, O. G.; Glushkov, V. A.; Karmanov, V. I.; Maiorova, O. A.; Shklyaev, Y. V. Russ. J. Org. Chem. 2009, 45, 360. [Zh. Org. Khim. 2009, 45, 372.]

  40. Nifontov, Y. V.; Glushkov, V. A.; Shklyaev, Y. V. Russ. Chem. Bull., Int. Ed. 2003, 52, 437. [Izv. Akad. Nauk, Ser. Khim. 2003, 418.]

  41. Glushkov, V. A.; Shklyaev, Y. V.; Sokol, V. I.; Sergienko, V. S.; Davidov, V. V. Mendeleev Commun. 1998, 8, 227.

    Article  Google Scholar 

  42. Ausheva, O. G.; Glushkov, V. A.; Shurov, S. N.; Shklyaev, Y. V. Russ. Chem. Bull., Int. Ed. 2001, 50, 1648. [Izv. Akad. Nauk, Ser. Khim. 2001, 1571.]

  43. Shklyaev, Y. V.; Ismagilov, R. R.; Rozhkova, Y. S.; Fatykhov, A. A.; Abdrakhmanov, I. B.; Tolstikov, A. G.; Dembitsky, V. M. Heteroat. Chem. 2004, 15, 471.

    Article  CAS  Google Scholar 

  44. Rozhkova, Y. S.; Galata, K. A.; Gorbunov, A. A.; Shklyaev, Y. V.; Ezhikova, M. A.; Kodess, M. I. Synlett 2014, 2617.

Download references

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to Jekaterina Bolsakova.

Additional information

Published in Khimiya Geterotsiklicheskikh Soedinenii, 2017, 53(11), 1167–1177

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Bolsakova, J., Jirgensons, A. The Ritter reaction for the synthesis of heterocycles. Chem Heterocycl Comp 53, 1167–1177 (2017). https://doi.org/10.1007/s10593-018-2189-y

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s10593-018-2189-y

Keywords

Navigation