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The chemoselective alkynylation of dihaloquinolines by the Sonogashira—Hagihara reaction

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Abstract

Conditions for the regioselective Sonogashira—Hagihara alkynylation of 4-chloro-6-iodo(bromo)quinolines were found and 6-alkynyl-4-chloroquinolines were obtained in 90—100% yields.

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References

  1. K. Sonogashira, J. Tohda, and N. Hagihara, Tetrahedron Lett., 1975, 16, 4467; K. Sonogashira, Comprehensive Organic Synthesis, Eds. B. M. Trost and I. Fleming, Pergamon Press, Oxford, 1991, 3, 521; K. Sonogashira, Metal-Catalyzed Cross-Coupling Reactions, Eds. F. Diederich and P. J. Stang, Wiley—VCH, Weinheim, 1998, 203; K. Sonogashira, Handbook of Organopalladium Chemistry for Organic Synthesis, Ed. E. Negishi, Wiley—VCH, New York, 2002, 493.

    Google Scholar 

  2. M. P. Lopez-Deber, L. Castedo, and J. R. Granja, Org. Lett., 2001, 3, 2823; D. T. Bong and M. R. Ghadiri, Org. Lett., 2001, 3, 2509.

    Google Scholar 

  3. I. I. Barabanov, L. G. Fedenok, and M. S. Shvartsberg, Izv. Akad. Nauk, Ser. Khim., 1998, 2327 [Russ. Chem. Bull., 1998, 47, 2256 (Engl. Transl.)]; M. S. Shvartsberg, I. I. Barabanov, and L. G. Fedenok, Mendeleev Commun., 1997, 98; L. Anastasia and E.-I. Negishi, Org. Lett., 2001, 3, 3111; U. Radhakrishnan and P. J. Stang, Org. Lett., 2001, 3, 859.

  4. M. Alami, F. Ferri, and G. Linstrumelle, Tetrahedron Lett., 1993, 34, 6403; M. Alami, B. Crousse, and F. Ferri, J. Organomet. Chem., 2001, 624, 114; D. Chemin and G. Linstrumelle, Tetrahedron, 1994, 50, 5335.

    Google Scholar 

  5. R. Menicagli, S. Samaritani, and S. Gori, Tetrahedron Lett., 1999, 40, 8419; M. R. Buchmeiser, T. Schareina, R. Kempe, and K. Wurst, J. Organomet. Chem., 2001, 634, 39.

    Google Scholar 

  6. J. W. Goodby, M. Hird, R. A. Lewis, and K. J. Toyne, Chem. Commun., 1996, 2719; K.-T. Wong, T. S. Hung, Y. Lin, C.-C. Wu, G.-H. Lee, S.-M. Peng, C. H. Chou, and Y. O. Su, Org. Lett., 2002, 4, 513.

    Google Scholar 

  7. H. Nakamura, M. Aizawa, D. Takeuchi, A. Murai, and O. Shimoura, Tetrahedron Lett., 2000, 41, 2185; T. Bach and L. Kruger, Tetrahedron Lett., 1998, 39, 1729; T. Bach and L. Kruger, Synlett, 1998, 1185; T. Bach and L. Kruger, Eur. J. Org. Chem., 1999, 2045.

    Google Scholar 

  8. L.-L. Gundersen, G. Langli, and F. Rise, Tetrahedron Lett., 1995, 36, 1945; G. Langli, L.-L. Gundersen, and F. Rise, Tetrahedron, 1996, 52, 5625; P. Dasa, C. P. Spearsb, A. H. Shahinianb, S. K. Dasguptaa, and N. G. Kundu, Bioorg. Med. Chem. Lett., 1996, 6, 2477.

    Google Scholar 

  9. J. Ellis, E. Gellert, and J. Robson, Aust. J. Chem., 1973, 26, 907; N. J. Leonard and S. N. Boyd, Jr., J. Org. Chem., 1946, 11, 419.

    Google Scholar 

  10. A. V. Tsvetkov, G. V. Latyshev, N. V. Lukashev, and I. P. Beletskaya, Tetrahedron Lett., 2002, 43, 7267.

    Google Scholar 

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Beletskaya, I.P., Latyshev, G.V., Tsvetkov, A.V. et al. The chemoselective alkynylation of dihaloquinolines by the Sonogashira—Hagihara reaction. Russian Chemical Bulletin 53, 189–193 (2004). https://doi.org/10.1023/B:RUCB.0000024849.57521.49

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  • DOI: https://doi.org/10.1023/B:RUCB.0000024849.57521.49

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