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