A convenient diversification of pyrrolo[2,3-b]-quinolines by iodonation and palladium-catalyzed coupling reactions

Heterocycles

Volumn 60, Issue 8, 2003, Pages 1821-1831

  Lee, Won Jung ^a   Gee, Moon Bae ^a   Yum, Eul Kgun ^a  

^a Chungnam National University   (South Korea)

Author keywords

[No Author keywords available]

Indexed keywords

2 IODOPYRROLO[2,3 B]QUINOLINE; 2 TRIMETHYLSILYLPYRROLO[2,3 B]QUINOLINE; ACETONITRILE; ALKENE; ALKYNE DERIVATIVE; BORIC ACID; ORGANOTIN COMPOUND; PALLADIUM; PYRROLE DERIVATIVE; QUINOLINE DERIVATIVE; TRIBUTYLTIN; TRIMETHYLSILYL DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CHEMICAL MODIFICATION; CHEMICAL REACTION; HECK REACTION; IODINATION; SYNTHESIS;

EID: 0042969130     PISSN: 03855414     EISSN: None     Source Type: Journal    
DOI: 10.3987/com-03-9798     Document Type: Article

References (26)

1. S. A. Yamashkin and M. A. Yurovskaya, Chemistry of Heterocyclic Compounds, 2001, 37, 1439.
2. (a) R. C. Larock and E. K. Yum, J. Am. Chem. Soc., 1991, 113, 6689.
3. (b) R. C. Larock, E. K. Yum, and D. Reffik, J. Org. Chem., 1998, 63, 7652.
4. (a) R. C. Larock, J. Organomet. Chem. 1999, 576, 111.
5. (b) R. C. Larock, Pure and Appl. Chem., 1999, 71, 1435.
6. (c) J. J. Li and G. W. Gribble, Palladium in Heterocyclic Chemistry, Pergamon, 2000, pp. 143-146.
7. (a) S. S. Park, J.-K. Choi, E. K. Yum, and D.-C. Ha, Tetrahedron Lett., 1998, 39, 627.
8. (b) S. M. Chi, J.-K. Choi, E. K. Yum, and D. Y. Chi, Tetrahedron Lett., 2000, 41, 919.
9. (c) M. S. Lee and E. K. Yum, Bull. Korean Chem. Soc., 2002, 23, 535.
10. (a) S. K. Kang, S. S. Park, S. S. Kim, J.-K. Choi, and E. K. Yum, Tetrahedron Lett., 1999, 40, 4379.
11. (b) E. K. Yum, S. S. Kang, S. S. Kim, J.-K. Choi, and H. G. Cheon, Bioorg. Med. Chem. Lett., 1999, 9, 1819.
12. (c) S. S. Kim, H. G. Cheon, S. K. Kang, E. K. Yum, and J.-K. Choi, Heterocycles 1998, 48, 221.
13. M. B. Gee, W. J. Lee, and E. K. Yum, Bull. Korean Chem. Soc., 2003, 24, in press.
14. (a) M. A. Khan and J. F. Da Rocha, Heterocycles, 1977, 6, 1229 and references cited therein.
15. (b) C. D. Smith and D. S. Lawrence, Chem. Abstract, 2001, 135, 303910u.
16. (c) Y. Fukuda and A. Tanioka, Chem. Abstract, 2000, 132, 151691w.
17. H. Zimmer, D. C. Armbruster, S. P. Khridia, and D. C. Lankin, Tetrahedron Lett., 1969, 4053.
18. M. B. Stringer, V. Candeloro, J. H. Bowie, R. H. Prager, L. M. Engelhardt, and A. H. White, J. Chem. Soc., Perkin Trans. I, 1984, 2529.
19. P. Shanmugam, T. K. Thiruvengadam, and V. T. Ramakrishnan, Synthesis, 1976, 393.
20. M. Murugesan, N. Soundarajan, K. Ramasamy, and P. Shanmugam, Synthesis, 1979, 352.
21. G. Himbert, W. Schwickerath, and G. Maas, Leibigs Ann. Chem., 1985, 1398.
22. M. L. Davis, B. J. Wakefield, and J. A. Wardell, Tetrahedron, 1992, 48, 939.
23. P. Molina, J. Alcantra, and C. Lopez-Leonardo, Tetrahedron, 1997, 53, 3281.
24. T. Tanaka, T. Iwakuma, M. Wagatsuma, and I. Iijima, J. Heterocycl. Chem., 1972, 9, 1355.
25. (a) H.-C. Zhang, H. Ye, and K. B. White, and B. E. Marynoff, Tetrahedron Lett., 2001, 42, 4751.
26. (b) D. P. Stamos, A. G. Taylor, and Y. Kishi, Tetrahedron Lett., 1996, 37, 8647.