DOI QR코드

DOI QR Code

Synthesis of Imidazo[1,5-α]quinolines and Imidazo[5,1-α]isoquinolines via the In-Mediated Allylation of Reissert Compounds

  • 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) ;
  • Park, Bo-Ram (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 : 2010.08.05
  • Accepted : 2010.08.25
  • Published : 2010.10.20

Abstract

Keywords

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, 66, 7065-7076. https://doi.org/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. 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
  12. 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
  13. 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
  14. 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
  15. 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
  16. Kim, Y. M.; Kim, S. H.; Kim, J. N. Bull. Korean Chem. Soc. 2010, 31, 1765-1768. https://doi.org/10.5012/bkcs.2010.31.6.1765
  17. Takamura, M.; Funabashi, K.; Kanai, M.; Shibasaki, M. J. Am. Chem. Soc. 2000, 122, 6327-6328. https://doi.org/10.1021/ja0010352
  18. Takamura, M.; Funabashi, K.; Kanai, M.; Shibasaki, M. J. Am. Chem. Soc. 2001, 123, 6801-6808. https://doi.org/10.1021/ja010654n
  19. Yadav, J. S.; Reddy, B. V. S.; Srinivas, M.; Sathaiah, K. Tetrahedron Lett. 2005, 46, 3489-3492. https://doi.org/10.1016/j.tetlet.2005.03.127
  20. Popp, F. D.; Kant, J. Heterocycles 1985, 23, 2193-2195. https://doi.org/10.3987/R-1985-09-2193
  21. Lizarraga, E.; Zabaleta, C.; Palop, J. A. Thermochim. Acta 2005, 427, 171-174. https://doi.org/10.1016/j.tca.2004.09.008
  22. Gibson, H. W.; Guilani, B. J. Org. Chem. 1990, 55, 4226-4229. https://doi.org/10.1021/jo00300a056
  23. Fuchs, C.; Bender, C.; Ziemer, B.; Liebscher, J. J. Heterocyclic Chem. 2008, 45, 1651-1658. https://doi.org/10.1002/jhet.5570450615
  24. Davey, D.; Erhardt, P. W.; Lumma, W. C., Jr.; Wiggins, J.; Sullivan, M.; Pang, D.; Cantor, E. J. Med. Chem. 1987, 30, 1337-1342. https://doi.org/10.1021/jm00391a012
  25. Iwao, M.; Kuraishi, T. J. Heterocyclic Chem. 1979, 16, 689-698. https://doi.org/10.1002/jhet.5570160416
  26. Kant, J. J. Heterocyclic Chem. 1990, 27, 2129-2132. https://doi.org/10.1002/jhet.5570270751
  27. Chernyak, N.; Gevorgyan, V. Angew. Chem. Int. Ed. 2010, 49, 2743-2746 https://doi.org/10.1002/anie.200907291
  28. Proenca, M. F.; Costa, M. Tetrahedron 2010, 66, 4542-4550. https://doi.org/10.1016/j.tet.2010.04.059
  29. Knueppel, D.; Martin, S. F. Angew. Chem. Int. Ed. 2009, 48, 2569-2571. https://doi.org/10.1002/anie.200806269
  30. Markey, M. D.; Kelly, T. R. J. Org. Chem. 2008, 73, 7441-7443. https://doi.org/10.1021/jo801694w
  31. Pettit, G. R.; Collins, J. C.; Knight, J. C.; Herald, D. L.; Nieman, R. A.; Williams, M. D.; Pettit, R. K. J. Nat. Prod. 2003, 66, 544-547. https://doi.org/10.1021/np020012t
  32. Funabashi, K.; Ratni, H.; Kanai, M.; Shibasaki, M. J. Am. Chem. Soc. 2001, 123, 10784-10785. https://doi.org/10.1021/ja016935c
  33. Langry, K. C. J. Org. Chem. 1991, 56, 2400-2404. https://doi.org/10.1021/jo00007a028
  34. Uff, B. C.; Ho, Y.-P.; Burford, D. L. W.; Popp, F. D. J. Heterocyclic Chem. 1987, 24, 1349-1351. https://doi.org/10.1002/jhet.5570240523

Cited by

  1. ChemInform Abstract: Synthesis of Imidazo[1,5-a]quinolines and Imidazo[5,1-a]isoquinolines via the In-Mediated Allylation of Reissert Compounds. vol.42, pp.10, 2011, https://doi.org/10.1002/chin.201110157
  2. Mild Double Allylboration Reactions of Nitriles and Acid Anhydrides Using Potassium Allyltrifluoroborate vol.78, pp.3, 2013, https://doi.org/10.1021/jo302194n
  3. Double Addition of Organometallics to Nitriles: Toward an Access to Tertiary Carbinamines vol.359, pp.2, 2016, https://doi.org/10.1002/adsc.201600727
  4. Synthesis and Applications of Imidazoquinolines: A Review vol.50, pp.2, 2018, https://doi.org/10.1080/00304948.2018.1433427
  5. Imidazoquinolines as Diverse and Interesting Building Blocks: Review of Synthetic Methodologies vol.85, pp.11, 2010, https://doi.org/10.3987/rev-12-747
  6. Recent Advances on Diversity Oriented Heterocycle Synthesis of Fused Quinolines and Its Biological Evaluation vol.41, pp.10, 2010, https://doi.org/10.1080/10406638.2019.1710856