Chemistry of Heterocyclic Compounds

, Volume 45, Issue 5, pp 524–530 | Cite as

Synthesis and some transformations of 5-(N-tosylaminomethyl)furfuryl alcohols

  • T. A. StroganovaEmail author
  • A. V. Butin

Preparative methods were developed for the synthesis of 5-(N-tosylaminomethyl)furfuryl alcohols, and their behavior during the action of acidic catalysts was studied. It was established that the furan ring of these compounds is stable in the presence of orthophosphoric acid in glacial acetic acid and that their hydroxyl and N-tosylaminomethyl groups are involved in the transformations.


N-tosylaminomethylfuran furylmethanols furfurylamine acylation acid catalysis formylation 


Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.


  1. 1.
    A. Balaban, A. Bota, and A. Zlota, Synthesis, 136 (1980).Google Scholar
  2. 2.
    I. G. Iovel, Yu. Sh. Gol'dberg, and M. V. Shimanskaya, Khim. Geterotsikl. Soedin., 746 (1989). [Chem. Heterocycl. Сотр., 25, 613 (1989)].Google Scholar
  3. 3.
    J. A. Marshall and X. J. Wang, J. Org. Chem., 56, 960 (1991).CrossRefGoogle Scholar
  4. 4.
    T. A. Stroganova, A. V. Butin, L. N. Sorotskaya, and V. G. Kul'nevich, RF Pat. 2165930; Byul. Izobr., No. 12, 425 (2001).Google Scholar
  5. 5.
    Т. Heiner, S. I. Kozhushkov, M. Noltemeyer, Т. Haumann, R. Boese, and A. De Meijere, Tetrahedron, 52, 12185 (1996).CrossRefGoogle Scholar
  6. 6.
    A. McCluskey, S. P. Ackland, M. С. Bowyer, M. L. Baldwin, J. Garner, С. С. Walkom, and J. A. Sakoff, Bioorg. Chem., 31, 68 (2003).CrossRefGoogle Scholar
  7. 7.
    B. J. McNelis, D. D. Sternbach, and A.T. MacPhail, Tetrahedron, 50, 6767 (1994).CrossRefGoogle Scholar
  8. 8.
    J. S. Yadav, R. Renduchintala, and L. Samala, Tetrahedron Lett, 35, 3617 (1994).CrossRefGoogle Scholar
  9. 9.
    J. Moursounidis and D. Wege, Tetrahedron Lett, 27, 3045 (1986).CrossRefGoogle Scholar
  10. 10.
    U. Lange, W. Plitzko, and S. Blechert, Tetrahedron, 51, 5781 (1995).CrossRefGoogle Scholar
  11. 11.
    D. Alonso, M. Pérez, G. Gómez, B. Covelo, and Y. Fall, Tetrahedron, 61, 2021 (2005).CrossRefGoogle Scholar
  12. 12.
    A. De Mico, R. Margarita, and G. Piancatelli, Tetrahedron Lett., 36, 3553 (1995).CrossRefGoogle Scholar
  13. 13.
    M. Takeuchi, T. Taniguchi, and K. Ogasawara, Synthesis, 341 (1999).Google Scholar
  14. 14.
    K. Takao, G. Watanabe, H. Yasui, and K. Tadano, Org. Lett., 4, 2941 (2002).CrossRefGoogle Scholar
  15. 15.
    X. Peng, A. Li, J. Lu, Q. Wang, X. Pan, and A. S. С. Chan, Tetrahedron, 58, 6799 (2002).CrossRefGoogle Scholar
  16. 16.
    P. A. Wender, K. D. Rice, and M. E. Schnute, J. Am. Chem. Soc, 119, 7897 (1997).CrossRefGoogle Scholar
  17. 17.
    S. Celanire, F. Marlin, J. E. Baldwin, and R. M. Adlington, Tetrahedron, 61, 3025 (2005).CrossRefGoogle Scholar
  18. 18.
    U. M. Krishna, G. S. С. Srikanth, and G. K. Trivedi, Tetrahedron Lett., 44, 8227 (2003).CrossRefGoogle Scholar
  19. 19.
    A. El Nemr, Tetrahedron, 56, 8579 (2000).CrossRefGoogle Scholar
  20. 20.
    E. Castagnino, S. Corsano, and P. Strappaveccia, Tetrahedron Lett, 26, 93 (1985).CrossRefGoogle Scholar
  21. 21.
    M. A. Ciufolini, С. Y. W. Hermann, Q. Dong, T. Shimizu, S. Swaminathan, and N. Xi, Synlett, 105 (1998).Google Scholar
  22. 22.
    Y.-M. Xu and W.-S. Zhou, J. Chem. Soc, Perkin Trans. 1, 741 (1997).Google Scholar
  23. 23.
    A. D. Mance, B. Borovicka, K. Jakopcič, G. Pavlovič, and I. Leban, J. Heterocycl. Chem., 39, 277 (2002).CrossRefGoogle Scholar
  24. 24.
    A. D. Mance, M. Šindler-Kulyk, K. Jakopcič, A. Hergold-Brundič, and A. Nagl, J. Heterocycl. Chem., 34, 1315 (1997).CrossRefGoogle Scholar
  25. 25.
    A. F. Oleinik and K. Yu. Novitskii, Dokl. Akad. Nauk, 186, 1334 (1969).Google Scholar
  26. 26.
    A.V. Butin, T. A. Stroganova, and V. G. Kul’nevich, in: Chemistry and Technology of Furan Compounds. Interuniversity Collection of Scientific Works [in Russian], Krasnodar Polytechnical Institute, Krasnodar (1997), Part 1, p. 21.Google Scholar
  27. 27.
    A. R. Katritzky, K. Suzuki, and S. K. Singh, Croat. Chem. Acta, 77 , 175 (2004).Google Scholar

Copyright information

© Springer Science+Business Media, Inc. 2009

Authors and Affiliations

  1. 1.Department of Organic ChemistryKuban State University of TechnologyKrasnodarRussia

Personalised recommendations