Bulletin of the Korean Chemical Society

  • 제26권2호
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  • Pages.323-326
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  • 2005
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  • 0253-2964(pISSN)
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  • 1229-5949(eISSN)
대한화학회 (Korean Chemical Society)
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Modified Friedländer Synthesis of Quinolines from N-Phenyl Cyclic Enaminones

  • Na, Jeong-Eun (Department of Chemistry and Institute of Basic Science, Chonnam National University) ;
  • Lee, Ka-Young (Department of Chemistry and Institute of Basic Science, Chonnam National University) ;
  • Park, Da-Youn (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)
  • 발행 : 2005.02.20
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참고문헌

  1. Thummel, R. P. Synlett 1992, 1
  2. Cheng, C.-C.; Yan, S.-J. Org. React. 1982, 28, 37
  3. Gladiali, S.; Chelucci, G.; Mudadu, M. S.; Gastaut, M.-A.; Thummel, R. P. J. Org. Chem. 2001, 66, 400 https://doi.org/10.1021/jo0009806
  4. Palimkar, S. S.; Siddiqui, S. A.; Daniel, T.; Lahoti, R. J.; Srinivasan, K. V. J. Org. Chem. 2003, 68, 9371 https://doi.org/10.1021/jo035153u
  5. Patteux, C.; Levacher, V.; Dupas, G. Org. Lett. 2003, 5, 3061 https://doi.org/10.1021/ol035049z
  6. McNaughton, B. R.; Miller, B. L. Org. Lett. 2003, 5, 4257 https://doi.org/10.1021/ol035333q
  7. Kim, J. L.; Kim, J. K.; Cho, H. N.; Kim, D. Y.; Kim, C. Y.; Hong, S. I. Macromolecules 2000, 33, 5880 https://doi.org/10.1021/ma000306q
  8. Arcadi, A.; Chiarini, M.; Giuseppe, S. D.; Marinelli, F. Synlett 2003, 203
  9. Fehnel, E. A. J. Heterocyclic Chem. 1967, 4, 565 https://doi.org/10.1002/jhet.5570040417
  10. Delfourne, E.; Darro, F.; Portefaix, P.; Galaup, C.; Bayssade, S.; Bouteille, A.; Corre, L. L.; Bastide, J.; Collignon, F.; Lesur, B.; Frydman, A.; Kiss, R. J. Med. Chem. 2002, 45, 3765 https://doi.org/10.1021/jm0208774
  11. Hsiao, Y.; Rivera, N. R.; Yasuda, N.; Hughes, D. L.; Reider, P. J. Org. Lett. 2001, 3, 1101 https://doi.org/10.1021/ol006785v
  12. Dormer, P. G.; Eng, K. K.; Farr, R. N.; Humphrey, G. R.; McWilliams, J. C.; Reider, P. J.; Sager, J. W.; Volante, R. P. J. Org. Chem. 2003, 68, 467 https://doi.org/10.1021/jo026203i
  13. Chen, J.; Deady, L. W.; Desneves, J.; Kaye, A. J.; Finlay, G. J.; Baguley, B. C.; Denny, W. A. Bioorg. Med. Chem. 2000, 8, 2461 https://doi.org/10.1016/S0968-0896(00)00179-6
  14. Strekowski, L.; Czarny, A.; Lee, H. J. Fluorine Chem. 2000, 104, 281 https://doi.org/10.1016/S0022-1139(00)00252-9
  15. Riesgo, E. C.; Jin, X.; Thummel, R. P. J. Org. Chem. 1996, 61, 3017 https://doi.org/10.1021/jo952164h
  16. Yadav, J. S.; Reddy, B. V. S.; Premalatha, K. Synlett 2004, 963
  17. Joos, K.; Pardo, M.; Schafer, W. J. Chem. Research (S) 1978, 406
  18. Wolfbeis, O. S. Synthesis 1977, 723
  19. Mahata, P. K.; Venkatesh, C.; Syam Kumar, U. K.; Ila, H.; Junjappa, H. J. Org. Chem. 2003, 68, 3966 https://doi.org/10.1021/jo034053l
  20. Manley, P. J.; Bilodeau, M. T. Org. Lett. 2004, 6, 2433 https://doi.org/10.1021/ol049165t
  21. Copp, B. R.; Hansen, R. P.; Appleton, D. R.; Lindsay, B. S.; Squire, C. J.; Clark, G. R.; Rickard, C. E. F. Synth. Commun. 1999, 29, 2665 https://doi.org/10.1080/00397919908086428
  22. Nishigaki, S.; Sato, J.; Shimizu, K.; Furukawa, K.; Senga, K.; Yoneda, F. Chem. Pharm. Bull. 1980, 28, 142 https://doi.org/10.1248/cpb.28.142
  23. Sabitha, G.; Babu, R. S.; Reddy, B. V. S.; Yadav, J. S. Synth. Commun. 1999, 29, 4403 https://doi.org/10.1080/00397919908086603
  24. Kim, J. M.; Na, J. E.; Kim, J. N. Tetrahedron Lett. 2003, 44, 6317 https://doi.org/10.1016/S0040-4039(03)01518-1
  25. Kim, J. M.; Na, J. E.; Lee, C. G.; Kim, J. N. Bull. Korean Chem. Soc. 2004, 25, 163 https://doi.org/10.5012/bkcs.2004.25.2.163
  26. Jenner, G. Tetrahedron Lett. 1996, 37, 3691 https://doi.org/10.1016/0040-4039(96)00620-X
  27. Gramain, J.-C.; Husson, H.-P.; Troin, Y. J. Org. Chem. 1985, 50, 5517 https://doi.org/10.1021/jo00350a016
  28. Stefani, H. A.; Costa, I. M.; Silva, D. de O. Synthesis 2000, 1526
  29. Lee, C. G.; Lee, K. Y.; Gowrisankar, S.; Kim, J. N. Tetrahedron Lett. 2004, 45, 7409 https://doi.org/10.1016/j.tetlet.2004.08.075
  30. Lee, K. Y.; Kim, J. M.; Kim, J. N. Tetrahedron 2003, 59, 385 https://doi.org/10.1016/S0040-4020(02)01518-1
  31. Kim, J. N.; Chung, Y. M.; Im, Y. J. Tetrahedron Lett. 2002, 43, 6209 https://doi.org/10.1016/S0040-4039(02)01314-X
  32. Kim, J. N.; Kim, H. S.; Gong, J. H.; Chung, Y. M. Tetrahedron Lett. 2001, 42, 8341 https://doi.org/10.1016/S0040-4039(01)01791-9
  33. Kim, J. N.; Lee, H. J.; Gong, J. H.; Lee, K. Y. Tetrahedron Lett. 2001, 42, 3737 https://doi.org/10.1016/S0040-4039(01)00552-4
  34. Kim, J. N.; Lee, K. Y.; Kim, H. S.; Kim, T. Y. Org. Lett. 2000, 2, 343 https://doi.org/10.1021/ol9903741
  35. Alt, G. H.; Speziale, A. J. J. Org. Chem. 1964, 29, 798 https://doi.org/10.1021/jo01027a008
  36. Lakhvich, F. A.; Rubinov, D. B.; Lis, L. G.; Rubinova, I. L. Zhur. Org. Khim. 1989, 25, 2089
  37. Nishigaki, S.; Sato, J.; Shimizu, K.; Furukawa, K.; Senga, K.; Yoneda, F. Chem. Pharm. Bull. 1980, 28, 142 https://doi.org/10.1248/cpb.28.142

피인용 문헌

  1. InCl3-Driven Regioselective Synthesis of Functionalized/Annulated Quinolines: Scope and Limitations vol.7, pp.4, 2012, https://doi.org/10.1002/asia.201100872
  2. Modified Friedlaender Synthesis of Quinolines from N-Phenyl Cyclic Enaminones. vol.36, pp.26, 2005, https://doi.org/10.1002/chin.200526084
  3. RuCl2(dmso)4 Catalyzes the Solvent-Free Indirect Friedländer Synthesis of Polysubstituted Quinolines from Alcohols vol.2007, pp.10, 2007, https://doi.org/10.1002/ejoc.200600945
  4. Synthesis of Polysubstituted Quinolines from the Acetates of Baylis-Hillman Adducts: Aza-Claisen Rearrangement as the Key Step vol.26, pp.6, 2005, https://doi.org/10.5012/bkcs.2005.26.6.1001
  5. A highly effective one-pot synthesis of quinolines from o-nitroarylcarbaldehydes vol.5, pp.1, 2005, https://doi.org/10.1039/b613775j
  6. Copper(II) triflate-catalyzed reactions for the synthesis of novel and diverse quinoline carboxylates vol.3, pp.44, 2005, https://doi.org/10.1039/c3ra44943b
  7. Catalytic Acceptorless Dehydrogenation of Amino Alcohols and 2-Hydroxybenzyl Alcohols for Annulation Reaction under Neutral Conditions vol.86, pp.13, 2005, https://doi.org/10.1021/acs.joc.1c00714