Browse > Article
http://dx.doi.org/10.5012/bkcs.2003.24.8.1193

Synthesis of Pyrrolo[2,3-b]quinolines by Palladium-catalyzed Heteroannulation  

Gee, Moon-Bae (Department of Chemistry, Chungnam National University)
Lee, Won-Jung (Department of Chemistry, Chungnam National University)
Yum, Eul-Kgun (Department of Chemistry, Chungnam National University)
Publication Information
Abstract
Palladium-catalyzed heteroannulation of 2-amino-3-iodoquinoline derivatives and 1-trimethylsilyl internal alkynes provided highly regioselective pyrrolo[2,3-b]quinolines with trimethylsilyl group next to the nitrogen atom in the pyrrole ring.
Keywords
Pyrrolo[2,3-b]quinolines; Palladium; Internal alkynes; Heteroannulation;
Citations & Related Records
Times Cited By KSCI : 1  (Citation Analysis)
Times Cited By Web Of Science : 5  (Related Records In Web of Science)
Times Cited By SCOPUS : 5
연도 인용수 순위
1 Yum, E. K.; Kang, S. S.;Kim, S. S.; Choi, J.-K.; Cheon, H. G. Bioorg. Med. Chem. Lett.1999, 9, 1819.   DOI   ScienceOn
2 Fukuda, Y.; Tanioka, A. WO 00/06571, 2000.
3 Himbert, G.; Schwickerath, W.; Maas, G. Leibigs Ann. Chem.1985, 1398.
4 Park, S. S.; Choi, J.-K.; Yum, E. K.; Ha, D.-C. TetrahedronLett. 1998, 39, 627.   DOI   ScienceOn
5 Marsais, F.; Gogard, A.; Queguiner, G. J. Heterocyclic Chem.1989, 26, 1589.   DOI
6 Larock, R. C.; Yum, E. K. J. Am. Chem. Soc. 1991, 113, 6689.   DOI
7 Tanaka, T.; Iwakuma, T.; Wagatsuma, M.; Iijima, I. J. HeterocyclicChem. 1972, 9, 1355.   DOI
8 Katritzky, R.; Rees, C. W. Comprehensive Heterocyclic Chemistry;Pergamon Press: 1984; Vol 4, pp 988-992, and references citedtherein.
9 Stringer, M. B.; Candeloro, V.; Bowie, J. H.; Prager, R. H.;Engelhardt, L. M.; White, A. H. J. Chem. Soc., Perkin Trans I1984, 2529.   DOI
10 Davis, M. L.; Wakefield, B. J.; Wardell, J. A. Tetrahedron 1992,48, 939.   DOI   ScienceOn
11 Larock, R. C. Pure and Appl. Chem. 1999, 71, 1435.   DOI   ScienceOn
12 Li, J. J.;Gribble, G. W. Palladium in Heterocyclic Chemistry; Pergamon:2000; pp 143-146.
13 Chi, S. M.; Choi, J.-K.; Yum, E. K.; Chi,D. Y. Tetrahedron. Lett. 2000, 41, 919.   DOI   ScienceOn
14 Khan, M. A.; Da Rocha, J. F. Heterocycles 1977, 6, 1229 andreferences cited therein.   DOI
15 Zimmer, H.; Armbruster, D. C.; Khridia, S. P.; Lankin, D. C.Tetrahedron Lett. 1969, 46, 4053.
16 Kang, S. K.; Park, S. S.; Kim, S. S.; Choi, J.-K.; Yum, E. K.Tetrahedron Lett. 1999, 40, 4379.   DOI   ScienceOn
17 Shanmugam, P.; Thiruvengadam, T. K.; Ramakrishnan, V. T.; Synthesis 1976, 393.
18 Smith, C. D.; Lawrence, D. S. WO 01/74790, 2001.
19 Larock, R. C.; Yum, E. K.; Reffik, D. J. Org. Chem. 1998, 63,7652.   DOI   ScienceOn
20 Lee, M. S.; Yum, E. K.Bull. Korean Chem. Soc. 2002, 23, 535.   DOI   ScienceOn
21 Queguiner, G. J. Heterocyclic Chem. 2000, 37,615.   DOI   ScienceOn
22 Murugesan, M.; Soundarajan, N.;Ramasamy, K.; Shanmugam, P. Synthesis 1979, 352.
23 Molina, P.; Alcantra, J.; Lopez-Leonardo, C. Tetrahedron 1997,53, 3281.   DOI   ScienceOn
24 Larock, R. C. J. Organomet. Chem. 1999, 576, 111.   DOI   ScienceOn
25 Kim, S. S.; Cheon, H. G.; Kang, S. K.; Yum, E.K.; Choi, J.-K. Heterocycles 1998, 48, 221.   DOI   ScienceOn