Skip to main content
Log in

Regioselective cycloaddition of C,N-diarylnitrones to arylallenes and of N-aryl-C-carbamoylnitrones to methyl buta-2,3-dienoate

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

Abstract

Cycloadditions of C,N-diarylnitrones to non-activated arylallenes and of N-aryl-C-carbamoylnitrones to methyl buta-2,3-dienoate regioselectively afforded mixtures of diastereoisomeric substituted 4-methylideneisoxazolidines.

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. Tufariello, J.J., 1,3-Dipolar Cycloaddition Chemistry, Padwa, A., Ed., New York: Wiley, 1984, vol. 2, p. 83.

    CAS  Google Scholar 

  2. Jones, R.C.F. and Martin, J.N., Synthetic Applications of 1,3-Dipolar Cycloaddition Chemistry Toward Hetero-cycles and Natural Products, Padwa, A. and Pearson, W.H., Eds., New York: Wiley, 2002, p. 1.

  3. Grigor’ev, I.A., Nitrile Oxides, Nitrones, and Nitronates in Organic Synthesis, Feuer, H., Ed., Hoboken, NJ: Wiley, 2007, p. 129.

  4. Pellissier, H., Tetrahedron, 2010, vol. 66, p. 8341.

    Article  CAS  Google Scholar 

  5. Pihno e Melo, T.M.V.D., Curr. Org. Chem., 2009, vol. 13, p. 1406.

    Article  Google Scholar 

  6. Pihno e Melo, T.M.V.D., Monatsh. Chem., 2011, vol. 142, p. 681.

    Article  Google Scholar 

  7. Padwa, A., Tomioka, Y., and Venkatramanan, M.K., Tetrahedron Lett., 1987, vol. 28, p. 755.

    Article  CAS  Google Scholar 

  8. Padwa, A., Matzinger, M., Tomioka, Y., and Venkatramanan, M.K., J. Org. Chem., 1988, vol. 53, p. 955.

    Article  CAS  Google Scholar 

  9. Padwa, A., Kline, D.M., and Norman, B.H., J. Org. Chem., 1989, vol. 54, p. 810.

    Article  CAS  Google Scholar 

  10. Padwa, A., Carter, S.P., Chiacchio, U., and Kline, D.M., Tetrahedron Lett., 1986, vol. 27, p. 2863.

    Article  Google Scholar 

  11. Padwa, A., Kline, D.M., Koehler, K.F., Matzinger, M., and Venkatramanan, M.K., J. Org. Chem., 1987, vol. 52, p. 3909.

    Article  CAS  Google Scholar 

  12. Dugovič, B., Fišera, L., and Reissig, H.-U., Eur. J. Org. Chem., 2008, p. 277.

    Google Scholar 

  13. Wu, X., Na, R., Liu, H., Wang, M., Zhong, J., and Guo, H., Tetrahedron Lett., 2012, vol. 53, p. 342.

    Article  CAS  Google Scholar 

  14. Zhao, B.-X. and Eguchi, S., Tetrahedron, 1997, vol. 53, p. 9575.

    Article  CAS  Google Scholar 

  15. Sasaki, T., Eguchi, S., and Hirako, Y., Tetrahedron Lett., 1976, vol. 17, p. 541.

    Article  Google Scholar 

  16. Padwa, A., Kline, D.M., and Perumattam, J., J. Org. Chem., 1989, vol. 54, p. 2862.

    Article  CAS  Google Scholar 

  17. Malinina, J., Tran, T.Q., Stepakov, A.V., Gurzhiy, V.V., Starova, G.L., Kostikov, R.R., and Molchanov, A.P., Tetrahedron Lett., 2014, vol. 55, p. 3663.

    Article  CAS  Google Scholar 

  18. Molchanov, A.P., Tran, T.Q., and Kostikov, R.R., Russ. J. Org. Chem., 2011, vol. 47, p. 269.

    Article  CAS  Google Scholar 

  19. 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.

    Article  Google Scholar 

  20. Anrade, M.M., Barros, M.T., and Pinto, R.C., Tetrahedron, 2008, vol. 64, p. 10 521.

    Article  Google Scholar 

  21. Baird, M.S., Nizovtsev, A.V., and Bolesov, I.G., Tetrahedron, 2002, vol. 58, p. 1581.

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to A. P. Molchanov.

Additional information

Original Russian Text © A.P. Molchanov, Yu.V. Malinina, R.R. Kostikov, A.V. Stepakov, 2015, published in Zhurnal Organicheskoi Khimii, 2015, Vol. 51, No. 3, pp. 384–388.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Molchanov, A.P., Malinina, Y.V., Kostikov, R.R. et al. Regioselective cycloaddition of C,N-diarylnitrones to arylallenes and of N-aryl-C-carbamoylnitrones to methyl buta-2,3-dienoate. Russ J Org Chem 51, 368–372 (2015). https://doi.org/10.1134/S1070428015030136

Download citation

  • Received:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1134/S1070428015030136

Keywords

Navigation