Russian Chemical Bulletin

, Volume 61, Issue 4, pp 871–876 | Cite as

Diastereoselective 1,3-dipolar cycloaddition of C,N-diaryl- and C-amido-N-arylnitrones to arylpropenones

  • A. P. Molchanov
  • T. Q. Tran
  • R. R. Kostikov
Full Articles


C,N-diarylnitrones and C-amido-N-arylnitrones add diastereoselectively to the substituted arylpropenones to give the substituted isoxazolidine possessing 3RS,4SR,5SR configuration. Replacement of the aryl groups either in the position 3 of chalcone or at the nitrogen atom of nitrone by the methyl group decreased the rate of cycloaddition.

Key words

nitrones arylpropenones cycloaddition isoxazolidines diastereoselectivity 


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  1. 1.
    J. J. Tufariello, in 1,3-Dipolar Cycloaddition Chemistry, Vol. 2, Ed. A. Padwa, Wiley, New York, 1984, pp. 83–168.Google Scholar
  2. 2.
    R. C. F. Jones, J. N. Martin, in Synthetic Application of 1,3-Dipolar Cycloaddition Chemistry Toward Heterocycles and Natural Products, Eds A. Padwa, W. H. Pearson, Wiley, New York, 2002, pp. 1–81.CrossRefGoogle Scholar
  3. 3.
    I. A. Grigorév, in Nitrile Oxides, Nitrones, and Nitronates in Organic Synthesis, Ed. H. Feuer, Wiley, Hoboken, New Jersey, 2007, pp. 129–424.CrossRefGoogle Scholar
  4. 4.
    V. Sridharan, S. Muthusubramanian, S. Sivasubramanian, K. Polborn, Tetrahedron, 2004, 60, 8881.CrossRefGoogle Scholar
  5. 5.
    D. Iannazzo, E. Brunaccini, S. V. Giofre, A. Piperno, G. Romeo, S. Ronsisvalle, M. A. Chicchio, G. Lanza, U. Chiacchio, Eur. J. Org. Chem., 2010, 5897.Google Scholar
  6. 6.
    S. Madapa, D. Sridhar, G. P. Yadav, P. R. Maulik, S. Batra, Eur. J. Org. Chem., 2007, 4343.Google Scholar
  7. 7.
    A. P. Molchanov, A. N. Lykholai, R. R. Kostikov, Zh. Org. Khim., 2001, 37, 1593 [Russ. J. Org. Chem. (Engl. Transl.), 2001, 37, 1517].Google Scholar
  8. 8.
    V. V. Diev, O. N. Stetsenko, T. Q. Tran, J. Kopf, R. R. Kostikov, A. P. Molchanov, J. Org. Chem., 2008, 73, 2396.CrossRefGoogle Scholar
  9. 9.
    V. V. Diev, T. Q. Tran, A. P. Molchanov, Eur. J. Org. Chem., 2009, 525.Google Scholar
  10. 10.
    A. P. Molchanov, T. Q. Tran, R. R. Kostikov, Zh. Org. Khim., 2011, 47, 279 [Russ. J. Org. Chem. (Engl. Transl.), 2011, 47, 269].Google Scholar
  11. 11.
    T. Q. Tran, V. V. Diev, A. P. Molchanov, Tetrahedron, 2011, 67, 2391.CrossRefGoogle Scholar
  12. 12.
    N. A. Akmanova, Kh. F. Sagitdinova., E. S. Balenkova, Khim. Geterotsikl. Soedin., 1982, 1192 [Chem. Heterocycl. Compd. (Engl. Transl.), 1982].Google Scholar
  13. 13.
    M. M. Andrade, M. T. Barros, R. C. Pinto, Tetrahedron, 2008, 64, 10521.CrossRefGoogle Scholar

Copyright information

© Springer Science+Business Media New York 2012

Authors and Affiliations

  • A. P. Molchanov
    • 1
  • T. Q. Tran
    • 1
  • R. R. Kostikov
    • 1
  1. 1.Saint Petersburg State UniversitySaint PetersburgRussian Federation

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