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Reductive cleavage and subsequent transformations of 5-oxa-6-azaspiro[2.4]heptane-1-carboxylates

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Abstract

Treatment of methyl 4,6-diaryl-5-oxa-6-azaspiro[2.4]heptane-1-carboxylates with zinc in acetic acid leads to cleavage of the N–O bond in the isoxazolidine ring with formation of 1,3-amino alcohols whose subsequent cyclization under the reaction conditions yields bi- or tricyclic lactams or lactones with retention of the three-membered ring.

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References

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

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

    CAS  Google Scholar 

  3. Brandi, A., Cicchi, S., Cordero, F.M., and Goti, A., Chem. Rev., 2003, vol. 103, p. 1213.

    Article  CAS  Google Scholar 

  4. Brandi, A. and Goti, A., Chem. Rev., 1998, vol. 98, p. 589.

    Article  CAS  Google Scholar 

  5. Goti, A., Cordero, F.M., and Brandi, A., Top. Curr. Chem., 1996, vol. 178, p. 1.

    Article  CAS  Google Scholar 

  6. Brandi, A., Cicchi, S., Cordero, F.M., and Goti, A., Chem. Rev., 2014, vol. 114, p. 7317.

    Article  CAS  Google Scholar 

  7. Cordero, F.M., de Sarlo, F., and Brandi, A., Monatsh. Chem., 2004, vol. 135, p. 649.

    Article  CAS  Google Scholar 

  8. Tran, T.Q., Diev, V.V., Starova, G.L., Gurzhiy, V.V., and Molchanov, A.P., Eur. J. Org. Chem., 2012, p. 2054.

    Google Scholar 

  9. 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 

  10. Huisgen, R., Hauck, H., Grashey, R., and Seidl, H., Chem. Ber., 1968, vol. 101, p. 2568.

    Article  CAS  Google Scholar 

  11. Huisgen, R., Hauck, H., Grashey, R., and Seidl, H., Chem. Ber., 1969, vol. 102, p. 736.

    Article  CAS  Google Scholar 

  12. LeBel, N.A., Post, M.E., and Whang, J.J., J. Am. Chem. Soc., 1964, vol. 86, p. 3759.

    Article  CAS  Google Scholar 

  13. Budziñska, A. and Sas, W., Tetrahedron, 2001, vol. 57, p. 2021.

    Article  Google Scholar 

  14. Tice, C.M. and Ganem, B., J. Org. Chem., 1983, vol. 48, p. 5048.

    Article  CAS  Google Scholar 

  15. Chiacchio, U., Piperno, A., Rescifina, A., Romeo, G., and Uccella, N., Tetrahedron, 1998, vol. 54, p. 5695.

    Article  CAS  Google Scholar 

  16. Tamura, O., Gotanda, K., Yoshino, J., Morita, Y., Terashima, R., Kikuchi, M., Miyawaki, T., Mita, N., Yamashita, M., Ishibashi, H., and Sakamoto, M., J. Org. Chem., 2000, vol. 65, p. 8544.

    Article  CAS  Google Scholar 

  17. Merino, P., Mates, J.A., Revuelta, J., Tejero, T., Chiacchio, U., Romeo, G., Iannazzo, D., and Romeo, R., Tetrahedron: Asymmetry, 2002, vol. 13, p. 173.

    Article  CAS  Google Scholar 

  18. Cordero, F.M., Pisaneschi, F., Batista, K.M., Valenza, S., Machetti, F., and Brandi, A., J. Org. Chem., 2005, vol. 70, p. 856.

    Article  CAS  Google Scholar 

  19. Cicchi, S., Goti, A., Brandi, A., Guarna, A., and de Sarlo, F., Tetrahedron Lett., 1990, vol. 31, p. 3351.

    Article  CAS  Google Scholar 

  20. Pisaneschi, F., Della Monica, C., Cordero, F.M., and Brandi, A., Tetrahedron Lett., 2002, vol. 43, p. 5711.

    Article  CAS  Google Scholar 

  21. Revuelta, J., Cicchi, S., and Brandi, A., Tetrahedron Lett., 2004, vol. 45, p. 8375.

    Article  CAS  Google Scholar 

  22. Molchanov, A.P. and Tran, T.Q., Russ. J. Org. Chem., 2012, vol. 48, p. 1283.

    Article  CAS  Google Scholar 

  23. Tran, T.Q., Diev, V.V., and Molchanov, A.P., Tetrahedron, 2011, vol. 67, p. 2391.

    Article  CAS  Google Scholar 

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Authors and Affiliations

  1. St. Petersburg State University, Universitetskaya nab. 7/9, St. Petersburg, 199034, Russia

    A. P. Molchanov, A. V. Stepakov & R. R. Kostikov

  2. School of Chemical Engineering, Hanoi University of Science and Technology, 1 Dai Co Viet Road, Hanoi, Viet Nam

    T. Q. Tran

Authors
  1. A. P. Molchanov
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  2. T. Q. Tran
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  3. A. V. Stepakov
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  4. R. R. Kostikov
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Correspondence to A. P. Molchanov.

Additional information

Original Russian Text © A.P. Molchanov, T.Q. Tran, A.V. Stepakov, R.R. Kostikov, 2016, published in Zhurnal Organicheskoi Khimii, 2016, Vol. 52, No. 3, pp. 424–428.

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Molchanov, A.P., Tran, T.Q., Stepakov, A.V. et al. Reductive cleavage and subsequent transformations of 5-oxa-6-azaspiro[2.4]heptane-1-carboxylates. Russ J Org Chem 52, 404–408 (2016). https://doi.org/10.1134/S1070428016030180

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  • DOI: https://doi.org/10.1134/S1070428016030180

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