Russian Journal of Organic Chemistry

, Volume 50, Issue 11, pp 1573–1578 | Cite as

Phosphorylation of Betti bases

  • K. E. Metlushka
  • D. N. Sadkova
  • L. N. Shaimardanova
  • K. A. Nikitina
  • O. A. Lodochnikova
  • O. N. Kataeva
  • V. A. Al’fonsov
Article

Abstract

Reaction of N-substituted 1-(α-aminobenzyl)-2-naphthols (Betti bases) with phosphorus(III) compounds followed by sulfurization afforded new cyclic phosphorylated and thiophosphorylated diastereomeric derivatives of N-substituted Betti bases. In most cases individual diastereomers were isolated and their characteristic spectral features were determined.

Keywords

Naphthol Diethylamino Anhydrous Benzene Amidophosphite Diethylamino Group 

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References

  1. 1.
    Kukhar, V.P. and Hudson, H.R., Aminophosphonic and aminophosphinic acids. Chemistry and biological activity, New York: J. Wiley & Sons, 2000.Google Scholar
  2. 2.
    Teichert, J.F. and Feringa, B.L., Angew. Chem., Int. Ed., 2010, vol. 49, p. 2486.CrossRefGoogle Scholar
  3. 3.
    Van Leeuwen, P.W.N.M., Kamer, P.C.J., Claver, C., Pàmies, O., and Diéguez, M., Chem. Rev., 2011, vol. 111, p. 2077.CrossRefGoogle Scholar
  4. 4.
    Cardellicchio, C., Capozzi, M.A.M., and Naso, F., Tetrahedron: Asymmetry, 2010, vol. 21, p. 507.CrossRefGoogle Scholar
  5. 5.
    Dong, Y., Li, R., Lu, J., Xu, X., Wang, X., and Hu, Y., J. Org. Chem., 2005, vol. 70, p. 8617.CrossRefGoogle Scholar
  6. 6.
    Alfonsov, V.A., Metlushka, K.E., McKenna, Ch.E., Kashemirov, B.A., Kataeva, O.N., Zheltukhin, V.F., Sadkova, D.N., and Dobrynin, A.B., Synlett., 2007, p. 488.Google Scholar
  7. 7.
    Bian, G., Yang, S., Huang, H., and Song, L., Synthesis, 2013, p. 899.Google Scholar
  8. 8.
    Wu, R., Chang, X., Lu, A., Wang, Y., Wu, G., Song, H., Zhou, Z., and Tang, C., Chem. Commun., 2011, vol. 47, p. 5034.CrossRefGoogle Scholar
  9. 9.
    Metlushka, K.E., Kashemirov, B.A., Zheltukhin, V.F., Sadkova, D.N., Büchner, B., Hess, C., Kataeva, O.N., McKenna, Ch.E., and Alfonsov, V.A., Chem. Eur. J., 2009, vol. 15, p. 6718.CrossRefGoogle Scholar
  10. 10.
    Cardellicchio, C., Ciccarella, G., Naso, F., Schingaro, E., and Scordari, F., Tetrahedron: Asymmetry, 1998, vol. 9, p. 3667.CrossRefGoogle Scholar
  11. 11.
    Palmieri, G., Tetrahedron: Asymmetry, 2000, vol. 11, p. 3361.CrossRefGoogle Scholar
  12. 12.
    Batyeva, E.S., Al’fonsov, V.A., Zamaletdinova, G.U., and Pudovik, A.N., Zh. Obshch. Khim., 1976, vol. 46, p. 2204.Google Scholar
  13. 13.
    Sheldrick, G.M., SADABS. Program for Absorption Corrections, Göttingen, Germany: University of Göttingen, 2004.Google Scholar
  14. 14.
    Sheldrick, G.M., Acta Cryst., Sect. A, 2008, vol. 64, p. 112.CrossRefGoogle Scholar
  15. 15.
    Farrugia, L.J., J. Appl. Cryst., 1999, vol. 32, p. 837.CrossRefGoogle Scholar
  16. 16.
    APEX (Version 2.1), SAINTPlus, Data Reduction and Correction Program Version 7.31A. Bruker Advanced X-Ray Solutions, Bruker XS Inc. Madison, Wisconsin, USA, 2006.Google Scholar

Copyright information

© Pleiades Publishing, Ltd. 2014

Authors and Affiliations

  • K. E. Metlushka
    • 1
  • D. N. Sadkova
    • 1
  • L. N. Shaimardanova
    • 1
  • K. A. Nikitina
    • 1
  • O. A. Lodochnikova
    • 1
  • O. N. Kataeva
    • 1
  • V. A. Al’fonsov
    • 1
  1. 1.Arbuzov Institute of Organic and Physical Chemistry, Kazan Scientific CenterRussian Academy of SciencesKazan, TatarstanRussia

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