Bulletin of the Korean Chemical Society

  • 제32권4호
  • /
  • Pages.1387-1390
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  • 2011
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  • 0253-2964(pISSN)
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  • 1229-5949(eISSN)
대한화학회 (Korean Chemical Society)
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Regioselective Synthesis of Fluorenones via the Consecutive In-Mediated Barbier Reaction, Pd-Catalyzed Cyclization, and Friedel-Crafts Reaction Starting from Baylis-Hillman Adducts

  • Kim, Ko-Hoon (Department of Chemistry and Institute of Basic Science, Chonnam National University) ;
  • Kim, Sung-Hwan (Department of Chemistry and Institute of Basic Science, Chonnam National University) ;
  • Lee, Ka-Young (Document and Image Division, National Forensic Service) ;
  • Kim, Jae-Nyoung (Department of Chemistry and Institute of Basic Science, Chonnam National University)
  • 투고 : 2010.01.23
  • 심사 : 2011.02.18
  • 발행 : 2011.04.20
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참고문헌

  1. Basavaiah, D.; Rao, A. J.; Satyanarayana, T. Chem. Rev. 2003, 103, 811. https://doi.org/10.1021/cr010043d
  2. Singh, V.; Batra, S. Tetrahedron 2008, 64, 4511. https://doi.org/10.1016/j.tet.2008.02.087
  3. Declerck, V.; Martinez, J.; Lamaty, F. Chem. Rev. 2009, 109, 1. https://doi.org/10.1021/cr068057c
  4. Ciganek, E. In Organic Reactions; Paquette, L. A., Ed.; John Wiley & Sons: New York, 1997; Vol. 51, pp 201-350.
  5. Kim, J. N.; Lee, K. Y. Curr. Org. Chem. 2002, 6, 627. https://doi.org/10.2174/1385272023374094
  6. Lee, K. Y.; Gowrisankar, S.; Kim, J. N. Bull. Korean Chem. Soc. 2005, 26, 1481. https://doi.org/10.5012/bkcs.2005.26.10.1481
  7. Krishna, P. R.; Sachwani, R.; Reddy, P. S. Synlett 2008, 2897.
  8. Gowrisankar, S.; Lee, H. S.; Kim, S. H.; Lee, K. Y.; Kim, J. N. Tetrahedron 2009, 65, 8769. https://doi.org/10.1016/j.tet.2009.07.034
  9. Kim, H. S.; Lee, H. S.; Kim, S. H.; Kim, J. N. Tetrahedron Lett. 2009, 50, 3154. https://doi.org/10.1016/j.tetlet.2008.11.127
  10. Kim, K. H.; Lee, H. S.; Kim, J. N. Tetrahedron Lett. 2009, 50, 1249. https://doi.org/10.1016/j.tetlet.2009.01.018
  11. Kim, S. H.; Kim, K. H.; Kim, H. S.; Kim, J. N. Tetrahedron Lett. 2008, 49, 1948. https://doi.org/10.1016/j.tetlet.2008.01.110
  12. Gowrisankar, S.; Lee, H. S.; Kim, J. M. Kim, J. N. Tetrahedron Lett. 2008, 49, 1670. https://doi.org/10.1016/j.tetlet.2007.12.133
  13. Lee, H. S.; Kim, S. H.; Gowrisankar, S.; Kim, J. N. Tetrahedron 2008, 64, 7183. https://doi.org/10.1016/j.tet.2008.05.087
  14. Lee, H. S.; Kim, J. M.; Kim, J. N. Tetrahedron Lett. 2007, 48, 4119. https://doi.org/10.1016/j.tetlet.2007.04.022
  15. Kim, S. J.; Kim, H. S.; Kim, T. H.; Kim, J. N. Bull. Korean Chem. Soc. 2007, 28, 1605. https://doi.org/10.5012/bkcs.2007.28.9.1605
  16. Kim, E. S.; Kim, K. H.; Kim, S. H.; Kim, J. N. Tetrahedron Lett. 2009, 50, 5098. https://doi.org/10.1016/j.tetlet.2009.06.124
  17. Tierney, M. T.; Grinstaff, M. W. J. Org. Chem. 2000, 65, 5355. https://doi.org/10.1021/jo0055133
  18. Han, Y.; Bisello, A.; Nakamoto, C.; Rosenblatt, M.; Chorev, M. J. Peptide Res. 2000, 55, 230. https://doi.org/10.1034/j.1399-3011.2000.00175.x
  19. Greenlee, M. L.; Laub, J. B.; Rouen, G. P.; DiNinno, F.; Hammond, M. L.; Huber, J. L.; Sundelof, J. G.; Hammond, G. G. Bioorg. Med. Chem. Lett. 1999, 9, 3225. https://doi.org/10.1016/S0960-894X(99)00567-3
  20. Perry, P. J.; Read, M. A.; Davies, R. T.; Gowan, S. M.; Reszka, A. P.; Wood, A. A.; Kelland, L. R.; Neidle, S. J. Med. Chem. 1999, 42, 2679. https://doi.org/10.1021/jm990084q
  21. Fan, C.; Wang, W.; Wang, Y.; Qin, G.; Zhao, W. Phytochemistry 2001, 57, 1255. https://doi.org/10.1016/S0031-9422(01)00168-6
  22. Paul, S.; Samanta, S.; Ray, J. K. Tetrahedron Lett. 2010, 51, 5604 https://doi.org/10.1016/j.tetlet.2010.08.062
  23. Sun, C.-L.; Liu, N.; Li, B.-J.; Yu, D.-G.; Wang, Y.; Shi, Z.-J. Org. Lett. 2010, 12, 184. https://doi.org/10.1021/ol902552v
  24. Thirunavukkarasu, V. S.; Parthasarathy, K.; Cheng, C.-H. Angew. Chem. Int. Ed. 2008, 47, 9462. https://doi.org/10.1002/anie.200804153
  25. Waldo, J. P.; Zhang, X.; Shi, F.; Larock, R. C. J. Org. Chem. 2008, 73, 6679. https://doi.org/10.1021/jo8009215
  26. Zhang, X.; Larock, R. C. Org. Lett. 2005, 7, 3973. https://doi.org/10.1021/ol0514597
  27. Campo, M. A.; Larock, R. C. Org. Lett. 2000, 2, 3675. https://doi.org/10.1021/ol006585j
  28. Qabaja, G.; Jones, G. B. Tetrahedron Lett. 2000, 41, 5317. https://doi.org/10.1016/S0040-4039(00)00848-0
  29. Qabaja, G.; Jones, G. B. J. Org. Chem. 2000, 65, 7187. https://doi.org/10.1021/jo0056186
  30. Reim, S.; Lau, M.; Langer, P. Tetrahedron Lett. 2006, 47, 6903. https://doi.org/10.1016/j.tetlet.2006.07.025
  31. Gruber, J.; Li, R. W. C.; Aguiar, L. H. J. M. C.; Benvenho, A. R. V.; Lessmann, R.; Hummelgen, I. A. J. Mater. Chem. 2005, 15, 517. https://doi.org/10.1039/b411063c
  32. Olah, G. A.; Mathew, T.; Farnia, M.; Prakash, S. Synlett 1999, 1067.
  33. Yu, Z.; Velasco, D. Tetrahedron Lett. 1999, 40, 3229. https://doi.org/10.1016/S0040-4039(99)00370-6
  34. Danheiser, R. L.; Gould, A. E.; de la Pradilla, R. F.; Helgason, A. L. J. Org. Chem. 1994, 59, 5514. https://doi.org/10.1021/jo00098a002
  35. Rodriguez, D.; Martinez-Esperon, F.; Navarro-Vazquez, A.; Castedo, L.; Dominguez, D.; Saa, C. J. Org. Chem. 2004, 69, 3842. https://doi.org/10.1021/jo0498213
  36. Morris, J. L.; Becker, C. L.; Fronczek, F. R.; Daly, W. H.; McLaughlin, M. L. J. Org. Chem. 1994, 59, 6484. https://doi.org/10.1021/jo00100a065
  37. Patra, A.; Ghorai, S. K.; De, S. R.; Mal, D. Synthesis 2006, 2556.
  38. Ferreira, S. B.; Kaiser, C. R.; Ferreira, V. F. Synlett 2008, 2625.
  39. Barluenga, J.; Trincado, M.; Rubio, E.; Gonzalez, J. M. Angew. Chem. Int. Ed. 2006, 45, 3140. https://doi.org/10.1002/anie.200504448
  40. Gonzalez-Cantalpiedra, E.; de Frutos, O.; Atienza, C.; Mateo, C.; Echavarren, A. M. Eur. J. Org. Chem. 2006, 1430.
  41. Banik, B. K.; Venkatraman, M. S.; Mukhopadhyay, C.; Becker, F. F. Tetrahedron Lett. 1998, 39, 7247. https://doi.org/10.1016/S0040-4039(98)01556-1
  42. Kim, K. H.; Lee, H. S.; Kim, S. H.; Kim, S. H.; Kim, J. N. Chem. Eur. J. 2010, 16, 2375. https://doi.org/10.1002/chem.200903029
  43. Streitwieser, A., Jr.; Brown, S. M. J. Org. Chem. 1988, 53, 904. https://doi.org/10.1021/jo00239a050
  44. 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
  45. Lee, C. G.; Lee, K. Y.; Lee, S.; Kim, J. N. Tetrahedron 2005, 61, 1493. https://doi.org/10.1016/j.tet.2004.11.082
  46. Kim, S. C.; Gowrisankar, S.; Kim, J. N. Bull. Korean Chem. Soc. 2005, 26, 1001. https://doi.org/10.5012/bkcs.2005.26.6.1001

피인용 문헌

  1. ChemInform Abstract: Regioselective Synthesis of Fluorenones via the Consecutive In-Mediated Barbier Reaction, Pd-Catalyzed Cyclization, and Friedel-Crafts Reaction Starting from Baylis-Hillman Adducts. vol.42, pp.34, 2011, https://doi.org/10.1002/chin.201134091
  2. CC Coupling Through Intramolecular Dual CH Activation Directed by a Removable Carboxylate Group: A Method for the Synthesis of Fluorenones under Mild Reaction Conditions vol.3, pp.6, 2014, https://doi.org/10.1002/ajoc.201402035
  3. ]quinoline-1,2-diones via Intramolecular Friedel-Crafts Cyclization Protocol vol.36, pp.11, 2015, https://doi.org/10.1002/bkcs.10539
  4. Ester-directed Ru-catalyzed C–O activation/C–C coupling reaction of ortho-methoxy naphthoates with organoboroneopentylates vol.52, pp.8, 2016, https://doi.org/10.1039/C5CC09121G
  5. Synthesis of Spiroindanyl-2-oxindoles via PPA-mediated Intramolecular Friedel-Crafts Reaction vol.38, pp.10, 2017, https://doi.org/10.1002/bkcs.11234
  6. Chemoselective synthesis of isolated and fused fluorenones and their photophysical and antiviral properties vol.16, pp.40, 2018, https://doi.org/10.1039/C8OB01733F
  7. Synthesis of 1-Substituted Fluorenones vol.36, pp.5, 2016, https://doi.org/10.1080/10406638.2015.1046609
  8. Synthesis of 1-indanones with a broad range of biological activity vol.13, pp.None, 2011, https://doi.org/10.3762/bjoc.13.48
  9. One-pot synthesis of benzo[b]fluorenones via a cobalt-catalyzed MHP-directed [3+2] annulation/ring-opening/dehydration sequence vol.55, pp.29, 2019, https://doi.org/10.1039/c9cc00948e
  10. On the Shape and Synthesis of Extended Fluorenones: Recent Advances and Upcoming Challenges vol.2022, pp.4, 2011, https://doi.org/10.1002/ejoc.202101032
  11. On the Shape and Synthesis of Extended Fluorenones: Recent Advances and Upcoming Challenges vol.2022, pp.4, 2011, https://doi.org/10.1002/ejoc.202101032