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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)
  • Published : 2003.08.20

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

References

  1. Katritzky, R.; Rees, C. W. Comprehensive Heterocyclic Chemistry;Pergamon Press: 1984; Vol 4, pp 988-992, and references citedtherein.
  2. Khan, M. A.; Da Rocha, J. F. Heterocycles 1977, 6, 1229 andreferences cited therein. https://doi.org/10.3987/R-1977-08-1229
  3. Smith, C. D.; Lawrence, D. S. WO 01/74790, 2001.
  4. Fukuda, Y.; Tanioka, A. WO 00/06571, 2000.
  5. Stringer, M. B.; Candeloro, V.; Bowie, J. H.; Prager, R. H.;Engelhardt, L. M.; White, A. H. J. Chem. Soc., Perkin Trans I1984, 2529. https://doi.org/10.1039/p19840002529
  6. Zimmer, H.; Armbruster, D. C.; Khridia, S. P.; Lankin, D. C.Tetrahedron Lett. 1969, 46, 4053.
  7. Shanmugam, P.; Thiruvengadam, T. K.; Ramakrishnan, V. T.; Synthesis 1976, 393.
  8. Murugesan, M.; Soundarajan, N.;Ramasamy, K.; Shanmugam, P. Synthesis 1979, 352.
  9. Himbert, G.; Schwickerath, W.; Maas, G. Leibigs Ann. Chem.1985, 1398.
  10. Davis, M. L.; Wakefield, B. J.; Wardell, J. A. Tetrahedron 1992,48, 939. https://doi.org/10.1016/S0040-4020(01)88196-5
  11. Molina, P.; Alcantra, J.; Lopez-Leonardo, C. Tetrahedron 1997,53, 3281. https://doi.org/10.1016/S0040-4020(97)00038-0
  12. Tanaka, T.; Iwakuma, T.; Wagatsuma, M.; Iijima, I. J. HeterocyclicChem. 1972, 9, 1355. https://doi.org/10.1002/jhet.5570090628
  13. Larock, R. C.; Yum, E. K. J. Am. Chem. Soc. 1991, 113, 6689. https://doi.org/10.1021/ja00017a059
  14. Larock, R. C.; Yum, E. K.; Reffik, D. J. Org. Chem. 1998, 63,7652. https://doi.org/10.1021/jo9803277
  15. Larock, R. C. J. Organomet. Chem. 1999, 576, 111. https://doi.org/10.1016/S0022-328X(98)01053-5
  16. Larock, R. C. Pure and Appl. Chem. 1999, 71, 1435. https://doi.org/10.1351/pac199971081435
  17. Li, J. J.;Gribble, G. W. Palladium in Heterocyclic Chemistry; Pergamon:2000; pp 143-146.
  18. Park, S. S.; Choi, J.-K.; Yum, E. K.; Ha, D.-C. TetrahedronLett. 1998, 39, 627. https://doi.org/10.1016/S0040-4039(97)10662-1
  19. Chi, S. M.; Choi, J.-K.; Yum, E. K.; Chi,D. Y. Tetrahedron. Lett. 2000, 41, 919. https://doi.org/10.1016/S0040-4039(99)02190-5
  20. Lee, M. S.; Yum, E. K.Bull. Korean Chem. Soc. 2002, 23, 535. https://doi.org/10.5012/bkcs.2002.23.4.535
  21. Kang, S. K.; Park, S. S.; Kim, S. S.; Choi, J.-K.; Yum, E. K.Tetrahedron Lett. 1999, 40, 4379. https://doi.org/10.1016/S0040-4039(99)00753-4
  22. Yum, E. K.; Kang, S. S.;Kim, S. S.; Choi, J.-K.; Cheon, H. G. Bioorg. Med. Chem. Lett.1999, 9, 1819. https://doi.org/10.1016/S0960-894X(99)00291-7
  23. Kim, S. S.; Cheon, H. G.; Kang, S. K.; Yum, E.K.; Choi, J.-K. Heterocycles 1998, 48, 221. https://doi.org/10.3987/COM-97-8041
  24. Marsais, F.; Gogard, A.; Queguiner, G. J. Heterocyclic Chem.1989, 26, 1589. https://doi.org/10.1002/jhet.5570260615
  25. Queguiner, G. J. Heterocyclic Chem. 2000, 37,615. https://doi.org/10.1002/jhet.5570370318

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