KCN-catalyzed C-C bond formation between imine and gem-difluoroalkene moieties: A facile synthesis of 2,4-disubstituted 3-fluoroquinolines

Chemistry Letters

Volumn 33, Issue 5, 2004, Pages 590-591

  Mori, Takashi ^a   Ichikawa, Junji ^a  

^a UNIVERSITY OF TOKYO   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ALKENE DERIVATIVE; CARBON; FLUORINE DERIVATIVE; POTASSIUM DERIVATIVE; QUINOLINE DERIVATIVE; STYRENE DERIVATIVE; VINYL DERIVATIVE;

ARTICLE; CATALYSIS; CHEMICAL BOND; CYCLIZATION; MOLECULAR INTERACTION; REACTION ANALYSIS; SUBSTITUTION REACTION; SYNTHESIS;

EID: 3242809711     PISSN: 03667022     EISSN: None     Source Type: Journal    
DOI: 10.1246/cl.2004.590     Document Type: Article

References (24)

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5. For the synthesis of ring-fluorinated quinolines, see: a) Ref. 1. b) J. Ichikawa, Y. Wada, H. Miyazaki, T. Mori, and H. Kuroki, Org. Lett., 5, 1455 (2003) and references therein. c) R. D. Chambers, M. Parsons, G. Sandford, C. J. Skinner, M. J. Atherton, and J. S. Moilliet, J. Chem. Soc., Perkin Trans. 1, 1999, 803 and references therein. d) L. Strekowski, A. S. Kiselyov, and M. Hojjat, J. Org. Chem., 59, 5886 (1994). e) G.-Q. Shi, S. Takagishi, and M. Schlosser, Tetrahedron, 50, 1129 (1994).
6. For the synthesis of ring-fluorinated quinolines, see: a) Ref. 1. b) J. Ichikawa, Y. Wada, H. Miyazaki, T. Mori, and H. Kuroki, Org. Lett., 5, 1455 (2003) and references therein. c) R. D. Chambers, M. Parsons, G. Sandford, C. J. Skinner, M. J. Atherton, and J. S. Moilliet, J. Chem. Soc., Perkin Trans. 1, 1999, 803 and references therein. d) L. Strekowski, A. S. Kiselyov, and M. Hojjat, J. Org. Chem., 59, 5886 (1994). e) G.-Q. Shi, S. Takagishi, and M. Schlosser, Tetrahedron, 50, 1129 (1994).
7. For the synthesis of ring-fluorinated quinolines, see: a) Ref. 1. b) J. Ichikawa, Y. Wada, H. Miyazaki, T. Mori, and H. Kuroki, Org. Lett., 5, 1455 (2003) and references therein. c) R. D. Chambers, M. Parsons, G. Sandford, C. J. Skinner, M. J. Atherton, and J. S. Moilliet, J. Chem. Soc., Perkin Trans. 1, 1999, 803 and references therein. d) L. Strekowski, A. S. Kiselyov, and M. Hojjat, J. Org. Chem., 59, 5886 (1994). e) G.-Q. Shi, S. Takagishi, and M. Schlosser, Tetrahedron, 50, 1129 (1994).
8. For the synthesis of ring-fluorinated quinolines, see: a) Ref. 1. b) J. Ichikawa, Y. Wada, H. Miyazaki, T. Mori, and H. Kuroki, Org. Lett., 5, 1455 (2003) and references therein. c) R. D. Chambers, M. Parsons, G. Sandford, C. J. Skinner, M. J. Atherton, and J. S. Moilliet, J. Chem. Soc., Perkin Trans. 1, 1999, 803 and references therein. d) L. Strekowski, A. S. Kiselyov, and M. Hojjat, J. Org. Chem., 59, 5886 (1994). e) G.-Q. Shi, S. Takagishi, and M. Schlosser, Tetrahedron, 50, 1129 (1994).
9. For the synthesis of ring-fluorinated quinolines, see: a) Ref. 1. b) J. Ichikawa, Y. Wada, H. Miyazaki, T. Mori, and H. Kuroki, Org. Lett., 5, 1455 (2003) and references therein. c) R. D. Chambers, M. Parsons, G. Sandford, C. J. Skinner, M. J. Atherton, and J. S. Moilliet, J. Chem. Soc., Perkin Trans. 1, 1999, 803 and references therein. d) L. Strekowski, A. S. Kiselyov, and M. Hojjat, J. Org. Chem., 59, 5886 (1994). e) G.-Q. Shi, S. Takagishi, and M. Schlosser, Tetrahedron, 50, 1129 (1994).
10. For reviews on ring-fluorinated heterocycles, see: a) M. J. Silvester, Adv. Heterocyclic Chem., 59, 1 (1994). b) M. J. Silvester, Aldrichimica Acta, 24, 31 (1991). c) "Organofluorine Chemistry, Principles and Commercial Applications," ed. by R. E. Banks, B. E. Smart, and J. C. Tatlow, Plenum, New York (1994).
11. For reviews on ring-fluorinated heterocycles, see: a) M. J. Silvester, Adv. Heterocyclic Chem., 59, 1 (1994). b) M. J. Silvester, Aldrichimica Acta, 24, 31 (1991). c) "Organofluorine Chemistry, Principles and Commercial Applications," ed. by R. E. Banks, B. E. Smart, and J. C. Tatlow, Plenum, New York (1994).
12. For reviews on ring-fluorinated heterocycles, see: a) M. J. Silvester, Adv. Heterocyclic Chem., 59, 1 (1994). b) M. J. Silvester, Aldrichimica Acta, 24, 31 (1991). c) "Organofluorine Chemistry, Principles and Commercial Applications," ed. by R. E. Banks, B. E. Smart, and J. C. Tatlow, Plenum, New York (1994).
13. For recent reports on quinoline synthesis, see: a) C. Wolf and R. Lerebours, J. Org. Chem., 68, 7077 (2003). b) K. Kobayashi, K. Yoneda, T. Mizumoto, H. Umakoshi, O. Morikawa, and H. Konishi, Tetrahedron Lett., 44, 4733 (2003) and references therein. c) J. N. Kim, H. J. Lee, K. Y. Lee, and H. S. Kim, Tetrahedron Lett., 42, 3737 (2001). d) C. S. Cho, B. H. Oh, J. S. Kim, T.-J. Kim, and S. C. Shim, Chem. Commun. 2000, 1885 and references therein.
14. For recent reports on quinoline synthesis, see: a) C. Wolf and R. Lerebours, J. Org. Chem., 68, 7077 (2003). b) K. Kobayashi, K. Yoneda, T. Mizumoto, H. Umakoshi, O. Morikawa, and H. Konishi, Tetrahedron Lett., 44, 4733 (2003) and references therein. c) J. N. Kim, H. J. Lee, K. Y. Lee, and H. S. Kim, Tetrahedron Lett., 42, 3737 (2001). d) C. S. Cho, B. H. Oh, J. S. Kim, T.-J. Kim, and S. C. Shim, Chem. Commun. 2000, 1885 and references therein.
15. For recent reports on quinoline synthesis, see: a) C. Wolf and R. Lerebours, J. Org. Chem., 68, 7077 (2003). b) K. Kobayashi, K. Yoneda, T. Mizumoto, H. Umakoshi, O. Morikawa, and H. Konishi, Tetrahedron Lett., 44, 4733 (2003) and references therein. c) J. N. Kim, H. J. Lee, K. Y. Lee, and H. S. Kim, Tetrahedron Lett., 42, 3737 (2001). d) C. S. Cho, B. H. Oh, J. S. Kim, T.-J. Kim, and S. C. Shim, Chem. Commun. 2000, 1885 and references therein.
16. For recent reports on quinoline synthesis, see: a) C. Wolf and R. Lerebours, J. Org. Chem., 68, 7077 (2003). b) K. Kobayashi, K. Yoneda, T. Mizumoto, H. Umakoshi, O. Morikawa, and H. Konishi, Tetrahedron Lett., 44, 4733 (2003) and references therein. c) J. N. Kim, H. J. Lee, K. Y. Lee, and H. S. Kim, Tetrahedron Lett., 42, 3737 (2001). d) C. S. Cho, B. H. Oh, J. S. Kim, T.-J. Kim, and S. C. Shim, Chem. Commun. 2000, 1885 and references therein.
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20. The classical Balz-Shiemann (fluorodediazotization) and Halex (halogen exchange) approaches are still extensively used. "Chemistry of Organic Fluorine Compounds II," ed. by M. Hudlicky and A. E. Pavlath, American Chemical Society, Washington, DC (1995).
21. J. Ichikawa, J. Fluorine Chem., 105, 257 (2000).
22. +); found 279.1385.
23. This type of bond formation was conducted in a stepwise fashion via Reissert products of isoquinolines. a) C. Kaiser, H.-J. Oh, B. J. Garcia-Slanga, A. C. Sulpizio, J. P. Hieble, J. E. Wawro, and L. I. Kruse, J. Med. Chem., 29, 2381 (1986). b) J. Kant, F. D. Popp, and B. C. Uff, J. Heterocycl. Chem., 22, 1065 (1985).
24. This type of bond formation was conducted in a stepwise fashion via Reissert products of isoquinolines. a) C. Kaiser, H.-J. Oh, B. J. Garcia-Slanga, A. C. Sulpizio, J. P. Hieble, J. E. Wawro, and L. I. Kruse, J. Med. Chem., 29, 2381 (1986). b) J. Kant, F. D. Popp, and B. C. Uff, J. Heterocycl. Chem., 22, 1065 (1985).