Advertisement

Chemistry of Heterocyclic Compounds

, Volume 46, Issue 9, pp 1071–1075 | Cite as

Arylsulfenylation of heterocyclic compounds with arylsulfenamides in the presence of phosphorus(V) oxochloride

  • R. L. AntipinEmail author
  • A. N. Chernysheva
  • E. K. Beloglazkina
  • N. V. Zyk
Article

The electrophilic sulfenylation of a series of indoles and pyrroles with arylsulfenamides in the presence of phophorus(V) oxohalide has been studied. It has been shown that arylsulfenylation of indoles led to products with substitution at position 3, while in the case of pyrrole it occurred at position 2.

Keywords

indoles pyrroles electrophilic substitution sulfenylation 

References

  1. 1.
    J. P. Berger, T. W. M. Doebber, Liebowitz, D. E. Moller, R. L. Mosley, R. I. Tolman, J. Ventre, B. B. Zhang, and G. Zhou, PCT Int. Appl. WO 0130343 (2001); www.espacenet.com
  2. 2.
    G. De Martino, G. La Regina, A. Coluccia, M. C. Edler, M. C. Barbera, A. Brancale, E. Wilcox, E. Hamel, M. Artico, and R. Silvestri, J. Med. Chem., 47, 6120 (2004).CrossRefGoogle Scholar
  3. 3.
    D. Potin, V. Parnet, J.-M. Teulon, F. Camborde, F. Caussade, J. Meignen, D. Provost, and A. Cloares, Bioorg. Med. Chem. Lett., 10, 805 (2000).CrossRefGoogle Scholar
  4. 4.
    T. M. Williams, T. M. Ciccarone, S. C. MacTough, C. S. Rooney, S. K. Balani, J. H. Condra, E. A. Emini, and V. V. Goldman, J. Med. Chem., 36, 1291 (1993).CrossRefGoogle Scholar
  5. 5.
    J. H. Hutchinson, D. Riendeau, C. Brideau, C. Chan, D. Delorme, D. Denis, J. P. Falgueyret, R. Fortin, and J. Guay, J. Med. Chem., 36, 2771 (1993).CrossRefGoogle Scholar
  6. 6.
    Y. Kawamonzen and Y. Mori, Jpn. Pat. 05196976; Chem. Abstr.,119, 237604 (1993).Google Scholar
  7. 7.
    B. Schnell and T. Kappe, Monatsh. Chem., 130, 1147 (1999).Google Scholar
  8. 8.
    Y. Maeda, M. Koyabu, T. Nishimura, and S. Uemura, J. Org. Chem., 69, 7688 (2004).CrossRefGoogle Scholar
  9. 9.
    M. Matsugi, K. Murata, K. Gotanda, H. Nambu, G. Anikulmar, K. Matsumoto, and Y. Kita, J. Org. Chem., 66, 2434 (2001).CrossRefGoogle Scholar
  10. 10.
    M. Shimizu, H. Fukazava, S. Shimada, and Y. Abe, Tetrahedron, 62, 2175 (2006).CrossRefGoogle Scholar
  11. 11.
    J. P. May, P. Fournier, J. Pellicelli, B. O. Patrick, and D. M. Perrin, J. Org. Chem., 70, 8424 (2005).CrossRefGoogle Scholar
  12. 12.
    M. Xia, S. Chen, and D. K. Bates, J. Org. Chem., 61, 9289 (1996).CrossRefGoogle Scholar
  13. 13.
    N. V. Zyk, E. K. Beloglazkina, and I. D. Titanuk, Russ. Chem. Bull., 47, 2434 (1998).CrossRefGoogle Scholar
  14. 14.
    N. V. Zyk, E. K. Beloglazkina, R. A. Gazzaeva, V. S. Tyurin, and I. D. Titanyuk, Phosphorus, Sulfur, Silicon, 155, 33 (1999).CrossRefGoogle Scholar
  15. 15.
    M. Raban and L.-J. Chern, J. Org. Chem., 45, 1688 (1980).CrossRefGoogle Scholar
  16. 16.
    K. S. Feldman and A. G. Karatjas, Org. Lett., 6, 2849 (2004).CrossRefGoogle Scholar
  17. 17.
    P. Hamel, J. Org. Chem., 67, 2854 (2002).CrossRefGoogle Scholar

Copyright information

© Springer Science+Business Media, Inc. 2010

Authors and Affiliations

  • R. L. Antipin
    • 1
    Email author
  • A. N. Chernysheva
    • 1
  • E. K. Beloglazkina
    • 1
  • N. V. Zyk
    • 1
  1. 1.M. V. Lomonosov Moscow State UniversityMoscowRussia

Personalised recommendations