Synthesis of β-and γ-carbolines by the palladium-catalyzed iminoannulation of internal alkynes

Organic Letters

Volumn 3, Issue 20, 2001, Pages 3083-3086

  Zhang, Haiming ^a   Larock, Richard C ^a  

^a IOWA STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ACETYLENE; BIPHENYLACETYLENE; CARBOLINE DERIVATIVE; DRUG DERIVATIVE; IMINE; ORGANOMETALLIC COMPOUND; PALLADIUM;

ARTICLE; CHEMISTRY; SYNTHESIS;

ACETYLENE; CARBOLINES; IMINES; ORGANOMETALLIC COMPOUNDS; PALLADIUM;

EID: 0035807570     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol010124w     Document Type: Article

References (34)

1. β-Carbolines: (a) Hino, T.; Nakagawa, M. J. Heteronycl. Chem. 1994, 31, 625.
2. (b) Baker, B. J. Alkaloids: Chem. Biol. Perspect. 1996, 10, 357.
3. (c) Love, B. E. Org. Prep. Proced. Int. 1996, 28, 1.
4. (d) Magnier, E.; Langlois, Y. Tetrahedron 1998, 43, 6201.
5. (e) Nakagawa, M. J. Heterocycl. Chem. 2000, 37, 567.
6. (f) Ohmoto, T.; Koike, K. In The Alkaloids; Brossi, A., Ed.; Academic: San Diego, 1989; Vol. 36, pp 135-170.
7. γ-Carbolines: (a) Matsukura, N.; Kawachi, T.; Morino, K.; Ohgaki, H.; Sugimura, T.; Takayama, S. Science 1981, 213, 346.
8. (b) Hibino, S.; Sugino, E.; Ogura, N.; Shintani, Y.; Sato, K. Heterocycles 1990, 30, 271.
9. For reviews, see: (a) Gribble, G. W. In The Alkaloids: Brossi, A., Ed.; Academic: San Diego, 1990; Vol. 39, Chapter 7.
10. (b) Tan, G. T.; Pezzuto, J. M. In Chemistry and Toxicology of Diverse Classes of Alkaloids; Blum, M. S., Ed.; Alaken, Inc.: Ft. Collins, CO, 1996; pp 1-119.
11. (c) For a recent report, see: Nguyen, C. H.; Lavelle, F.; Riou, J.-F.; Bissery, M.-C.; Huel, C.; Bisagni, E. Anti-Cancer Drug Des. 1992, 7, 235.
12. (a) Iwaki, T.; Yasuhara, A.; Sakamoto, T. J. Chem. Soc., Perkin Trans 1 1999, 1505.
13. (b) Snyder, S. A.; Vosburg, D. A.; Jarvis, M. G.; Markgraf, J. H. Tetrahedron 2000, 56, 5329.
14. (c) Engler, T.; Wanner, J. J. Org. Chem. 2000, 65, 2444.
15. For reviews, see: (a) Larock, R. C. J. Organomet. Chem. 1999, 576, 111.
16. (b) Larock, R. C. Palladium-Catalyzed Annulation. In Perspectives in Organopalladium Chemistry for the XXI Century; Tsuji, J., Ed.; Elsevier Press: Lausanne, Switzerland, 1999; pp 111-124.
17. (c) Larock, R. C. Pure Appl. Chem. 1999, 71, 1435.
18. (a) Larock, R. C.; Yum, E. K. J. Am. Chem. Soc. 1991, 113, 6689.
19. (b) Larock, R. C.; Yum, E. K.; Refvik, M. D. J. Org. Chem. 1998, 63, 7652.
20. (a) Roesch, K. R.; Larock, R. C. Org. Lett. 1999, 1, 1551.
21. (b) Roesch, K. R.; Larock, R. C. J. Org. Chem. 2001, 66, 412.
22. Larock, R. C.; Yum, E. K.; Doty, M. J.; Sham, K. K. C. J. Org. Chem. 1995, 60, 3270.
23. Larock, R. C.; Doty, M. J.; Han, X. J. Org. Chem. 1999, 64, 8770.
24. Larock, R. C.; Han, X.; Doty, M. J. Tetrahedron Lett. 1998, 39, 5713.
25. Larock, R. C.; Doty, M. J.; Cacchi, S. J. J. Org. Chem. 1993, 58, 4579.
26. (a) Larock, R. C.; Doty, M. J.; Tian, Q.; Zenner, J. M. J. Org. Chem. 1997, 62, 7536.
27. (b) Larock, R. C.; Tian, Q. J. Org. Chem. 1998, 63, 2002.
28. Roesch, K. R.; Larock, R. C. J. Org. Chem. 1998, 63, 5306.
29. 4. Removal of the solvent afforded 0.98 g (100%) of the imine as a yellow solid.
30. (a) Mann, G.; Hartwig, J. F.; Driver, M. S.; Fernández-Rivas, C. J. Am. Chem. Soc. 1998, 120, 827.
31. (b) Old, D. W.; Harris, M. C.; Buchwald, S. L. Org. Lett. 2000, 2, 1403.
32. (c) Watanabe, M.; Nishiyama, M.; Yamamoto, T.; Koie, Y. Tetrahedron Lett. 2000, 41, 481.
33. (a) Wu, G.; Rheingold, A. L.; Geib, S. J.; Heck, R. F. Organometallics 1987, 6, 1941.
34. (b) Wu, G.; Geib, S. J.; Rheingold, A. L.; Heck, R. F. J. Org. Chem. 1988, 53, 3238.