Skip to main content
Log in

Regio- and stereoselective (3 + 2)-cycloaddition of nitrile oxides and nitrones to N-vinylindole

  • Published:
Russian Journal of Organic Chemistry Aims and scope Submit manuscript

Abstract

1,3-Dipolar cycloaddition of nitrile oxides and nitrones to N-vinylindole proceeds regioselectively at the exocyclic multiple bond to form 5-indolyl-substituted isoxazolines and isoxazolidines in good yields.

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. Van Order, R.B. and Lindwall, H.G., Chem. Rev., 1942, vol. 30, p. 69. doi 10.1021/cr60095a004

    Article  Google Scholar 

  2. Kochanowska-Karamyan, A.J., and Hamann, M.T., Chem. Rev., 2010, vol. 110, p. 4489. doi 10.1021/cr900211p

    Article  CAS  Google Scholar 

  3. Cacchi, S. and Fabrizi, G., Chem. Rev., 2005, vol. 105, p. 2873. doi 10.1021/cr040639b

    Article  CAS  Google Scholar 

  4. Shiri, M., Chem. Rev., 2012, vol. 112, p. 3508. doi 10.1021/cr2003954

    Article  CAS  Google Scholar 

  5. Bruche, L. and Zecchi, G., J. Org. Chem., 1983, vol. 48, p. 2772. doi 10.1021/jo00164a029

    Article  CAS  Google Scholar 

  6. Caramella, P., Coda Corsico, A., Corsaro, A., Del Monte, D., and Albini, F.M., Tetrahedron, 1982, vol. 38, p. 173. doi 10.1016/0040-4020(82)85063-1

    Article  CAS  Google Scholar 

  7. Malamidou-Xenikaki, E. and Coutouli-Argyropoulou, E., Lieb. Ann., 1992, p. 75. doi 10.1002/jlac.199219920115

    Google Scholar 

  8. Cho, S.Yu., Ahn, J.H., Ha, J.D., Kang, S.K., Baek, J.Y., Han, S.S., Shin, E.Y., Kim, S.S., Kim, K.R., Cheon, H.G., and Choi, J.-K., Bull. Korean Chem. Soc., 2003, vol. 24, p. 1455. doi 10.5012/bkcs.2003.24.10.1455

    Article  CAS  Google Scholar 

  9. Laude, B., Soufiaoui, M., and Arriau, J., J. Heterocycl. Chem., 1977, vol. 14, p. 1183. doi 10.1002/jhet.5570140711

    Article  CAS  Google Scholar 

  10. Benincori, T., Sannicolo, F., Trimarco, L., Bonati, L., Grandi, S., Pitea, D., and Gatti, C., J. Phys. Org. Chem., 1998, vol. 11, p. 455.

    Article  CAS  Google Scholar 

  11. Liu, H., Zheng, C., and You, S.-L., J. Org. Chem., 2014, vol. 79, p. 1047. doi 10.1021/jo402511b

    Article  CAS  Google Scholar 

  12. Awata, A. and Arai, T., Angew. Chem., Int. Ed., 2014, vol. 53, p. 10462. doi 10.1002/anie.201405223

    Article  CAS  Google Scholar 

  13. Gerten, A.L. and Stanley, L.M., Org. Chem. Front., 2016, p. 339. doi 10.1039/C5QO00346F

    Google Scholar 

  14. Mejia-Oneto, J.M. and Padwa, A., Org. Lett., 2006, vol. 8, p. 3275. doi 10.1021/ol061137i

    Article  CAS  Google Scholar 

  15. Yuan, Z.Q., Ishikawa, H., and Boger, D.L., Org. Lett., 2005, vol. 7, p. 741. doi 10.1021/ol050017s

    Article  CAS  Google Scholar 

  16. Choi, Y., Ishikawa, H., Velcicky, J., Elliott, G.I., Miller, M.M., and Boger, D.L., Org. Lett., 2005, vol. 7, p. 4539. doi 10.1021/ol051975x

    Article  CAS  Google Scholar 

  17. Ishikawa, H., Elliott, G.I., Velcicky, J., Choi, Y., and Boger, D.L., J. Am. Chem. Soc., 2006, vol. 128, p. 10596. doi 10.1021/ja061256t

    Article  CAS  Google Scholar 

  18. Molchanov, A.P., Savinkov, R.S., Stepakov, A.V., Starova, G.L., Kostikov, R.R., Barnakova, V.S., and Ivanov, A.V., Synthesis, 2014, vol. 46, p. 771. doi 10.1055/s-0033-1340479

    Article  Google Scholar 

  19. Molchanov, A.P., Sirotkina, E.V., Efremova, M.M., Kostikov, R.R., Ivanov, A.V., and Shcherbakova, V.S., Russ. J. Org. Chem., 2015, vol. 51, p. 640. doi 10.1134/S1070428015050097

    Article  CAS  Google Scholar 

  20. Efremova, M.M., Molchanov, A.P., Stepakov, A.V., Kostikov, R.R., Shcherbakova, V.S., and Ivanov, A.V., Tetrahedron, 2015, vol. 71, p. 2071. doi 10.1016/j.tet.2015.02.058

    Article  CAS  Google Scholar 

  21. Bogdal, D. and Jaskot, K., Synth. Commun., 2000, vol. 30, p. 3341. doi 10.1080/00397910008086974

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to M. M. Efremova.

Additional information

Original Russian Text © M.M. Efremova, R.R. Kostikov, A.G. Larina, A.P. Molchanov, 2017, published in Zhurnal Organicheskoi Khimii, 2017, Vol. 53, No. 2, pp. 251–254.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Efremova, M.M., Kostikov, R.R., Larina, A.G. et al. Regio- and stereoselective (3 + 2)-cycloaddition of nitrile oxides and nitrones to N-vinylindole. Russ J Org Chem 53, 246–250 (2017). https://doi.org/10.1134/S107042801702018X

Download citation

  • Received:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1134/S107042801702018X

Navigation