Bulletin of the Korean Chemical Society

Korean Chemical Society (대한화학회)
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Synthesis of Dienamides via the Reaction of Nitrile with Allylindium Reagents and Intramolecular Acyl Group Quenching Cascade

  • Kim, Sung-Hwan (Department of Chemistry and Institute of Basic Science, Chonnam National University) ;
  • Kim, Yu-Mi (Department of Chemistry and Institute of Basic Science, Chonnam National University) ;
  • Kim, Jae-Nyoung (Department of Chemistry and Institute of Basic Science, Chonnam National University)
  • Received : 2010.06.07
  • Accepted : 2010.06.14
  • Published : 2010.08.20
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Abstract

Various dienamide derivatives were synthesized in reasonable yields from benzonitriles having an amide moiety at the ortho-position, via the sequential (i) In-mediated allylation of nitrile moiety to form an imine intermediate, (ii) intramolecular quenching of an acyl group by the imine intermediate, and (iii) a proton transfer to dienamide.

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References

  1. Auge, J.; Lubin-Germain, N.; Uziel, J. Synthesis 2007, 1739-1764.
  2. Kargbo, R. B.; Cook, G. R. Curr. Org. Chem. 2007, 11, 1287-1309. https://doi.org/10.2174/138527207782023139
  3. Lee, P. H. Bull. Korean Chem. Soc. 2007, 28, 17-28. https://doi.org/10.5012/bkcs.2007.28.1.017
  4. Li, C.-J.; Chan, T.-H. Tetrahedron 1999, 55, 11149-11176. https://doi.org/10.1016/S0040-4020(99)00641-9
  5. Pae, A. N.; Cho, Y. S. Curr. Org. Chem. 2002, 6, 715-737. https://doi.org/10.2174/1385272023374030
  6. Nair, V.; Ros, S.; Jayan, C. N.; Pillai, B. S. Tetrahedron 2004, 60, 1959-1982. https://doi.org/10.1016/j.tet.2003.12.037
  7. Podlech, J.; Maier, T. C. Synthesis 2003, 633-655.
  8. Kim, S. H.; Lee, H. S.; Kim, K. H.; Kim, S. H.; Kim, J. N. Tetrahedron 2010, DOI: 10.1016/j.tet.2010.05.103.
  9. Fujiwara, N.; Yamamoto, Y. Tetrahedron Lett. 1998, 39, 4729-4732. https://doi.org/10.1016/S0040-4039(98)00929-0
  10. Fujiwara, N.; Yamamoto, Y. J. Org. Chem. 1999, 64, 4095-4101. https://doi.org/10.1021/jo990160x
  11. Jin, S.-J.; Araki, S.; Butsugan, Y. Bull. Chem. Soc. Jpn. 1993, 66, 1528-1532. https://doi.org/10.1246/bcsj.66.1528
  12. Ranu, B. C.; Das, A. Tetrahedron Lett. 2004, 45, 6875-6877. https://doi.org/10.1016/j.tetlet.2004.07.098
  13. Kim, S. H.; Lee, H. S.; Kim, K. H.; Kim, J. N. Tetrahedron Lett. 2009, 50, 1696-1698 https://doi.org/10.1016/j.tetlet.2009.01.149
  14. Kim, S. H.; Kim, S. H.; Lee, K. Y.; Kim, J. N. Tetrahedron Lett. 2009, 50, 5744-5747. https://doi.org/10.1016/j.tetlet.2009.07.140
  15. Kim, S. H.; Lee, H. S.; Kim, K. H.; Kim, J. N. Tetrahedron Lett. 2009, 50, 6476-6479. https://doi.org/10.1016/j.tetlet.2009.09.013
  16. Kim, S. H.; Kim, S. H.; Kim, K. H.; Kim, J. N. Tetrahedron Lett. 2010, 51, 860-862. https://doi.org/10.1016/j.tetlet.2009.12.034
  17. Kim, S. H.; Kim, S. H.; Kim, T. H.; Kim, J. N. Tetrahedron Lett. 2010, 51, 2774-2777. https://doi.org/10.1016/j.tetlet.2010.03.076
  18. Purushottamachar, P.; Khandelwal, A.; Vasaitis, T. S.; Bruno, R. D.; Gediya, L. K.; Njar, V. C. O. Bioorg. Med. Chem. 2008, 16, 3519-3529. https://doi.org/10.1016/j.bmc.2008.02.031
  19. Aissaoui, H.; Koberstein, R.; Zumbrunn, C.; Gatfield, J.; Brisbare-Roch, C.; Jenck, F.; Treiber, A.; Boss, C. Bioorg. Med. Chem. Lett. 2008, 18, 5729-5733. https://doi.org/10.1016/j.bmcl.2008.09.079
  20. Mitchell, J. M.; Shaw, J. T. Angew. Chem. Int. Ed. 2006, 45, 1722-1726. https://doi.org/10.1002/anie.200503341
  21. Nummert, V.; Piirsalu, M.; Maemets, V.; Koppel, I. J. Phys. Org. Chem. 2005, 18, 1138-1144. https://doi.org/10.1002/poc.967
  22. Clark, A. J.; Geden, J. V.; Thom, S.; Wilson, P. J. Org. Chem. 2007, 72, 5923-5926. https://doi.org/10.1021/jo070680p
  23. Katritzky, A. R.; Ignatchenko, A. V.; Lang, H. J. Org. Chem. 1995, 60, 4002-4005. https://doi.org/10.1021/jo00118a015
  24. Couture, A.; Bochu, C.; Grandclaudon, P. Tetrahedron Lett. 1989, 30, 6865-6866. https://doi.org/10.1016/S0040-4039(01)93373-8
  25. Teoh, E.; Campi, E. M.; Jackson, W. R.; Robinson, A. J. Chem. Commun. 2002, 978-979.
  26. Teoh, E.; Campi, E. M.; Jackson, W. R.; Robinson, A. J. New. J. Chem. 2003, 27, 387-394. https://doi.org/10.1039/b209087m
  27. Burk, M. J.; Allen, J. G.; Kiesman, W. F. J. Am. Chem. Soc. 1998, 120, 657-663. https://doi.org/10.1021/ja9731074
  28. Shen, Y.-D.; Tian, Y.-X.; Bu, X.-Z.; Gu, L.-Q. Eur. J. Med. Chem. 2009, 44, 3915-3921. https://doi.org/10.1016/j.ejmech.2009.04.016
  29. Hoshina, Y.; Doi, T.; Takahashi, T. Tetrahedron 2007, 63, 12740-12746.. https://doi.org/10.1016/j.tet.2007.09.078
  30. Biolatto, B.; Kneeteman, M.; Mancini, P. Tetrahedron Lett. 1999, 40, 3343-3346. https://doi.org/10.1016/S0040-4039(99)00511-0
  31. Murphy, J. P.; Nieuwenhuyzen, M.; Reynolds, K.; Sarma, P. K. S.; Stevenson, P. J. Tetrahedron Lett. 1995, 36, 9533-9536. https://doi.org/10.1016/0040-4039(95)02040-3
  32. Chigr, M.; Fillion, H.; Rougny, A.; Berlion, M.; Riondel, J.; Beriel, H. Chem. Pharm. Bull. 1990, 38, 688-691. https://doi.org/10.1248/cpb.38.688
  33. Martin, S. F.; Li, W. J. Org. Chem. 1991, 56, 642-650. https://doi.org/10.1021/jo00002a029
  34. Martin, S. F.; Li, W. J. Org. Chem. 1989, 54, 265-268. https://doi.org/10.1021/jo00263a002

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