Bulletin of the Korean Chemical Society

  • 제33권1호
  • /
  • Pages.333-336
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  • 2012
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  • 0253-2964(pISSN)
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  • 1229-5949(eISSN)
대한화학회 (Korean Chemical Society)
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Direct Lactamization of Azido Amides via Staudinger-Type Reductive Cyclization

  • Heo, In-Jung (Department of Chemistry, Kyungpook National University) ;
  • Lee, Su-Jeong (Department of Chemistry, Kyungpook National University) ;
  • Cho, Chang-Woo (Department of Chemistry, Kyungpook National University)
  • 투고 : 2011.11.11
  • 심사 : 2011.11.18
  • 발행 : 2012.01.20
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참고문헌

  1. Pal, A. P. J.; Kadigachalam, P.; Mallick, A.; Doddi, V. R.; Vankar, Y. D. Org. Biomol. Chem. 2011, 9, 809. https://doi.org/10.1039/c0ob00555j
  2. Szostak, M.; Aube, J. Org. Biomol. Chem. 2011, 9, 27. https://doi.org/10.1039/c0ob00215a
  3. Kim, M. H.; Choi, Y. L.; Heo, J.-N.; Min, Y. K.; Kim, S. H. Bull. Korean Chem. Soc. 2010, 31, 2047. https://doi.org/10.5012/bkcs.2010.31.7.2047
  4. Mehta, P. D.; Sengar, N. P. S.; Pathak, A. K. Eur. J. Med. Chem. 2010, 45, 5541. https://doi.org/10.1016/j.ejmech.2010.09.035
  5. Lim, S.-H.; Mahmood, K.; Komiyama, K.; Kam, T.-S. J. Nat. Prod. 2008, 71, 1104. https://doi.org/10.1021/np800123g
  6. Oshiro, Y.; Sakurai, Y.; Sato, S.; Kurahashi, N.; Tanaka, T.; Kikuchi, T.; Tottori, K.; Uwahodo, Y.; Miwa, T.; Nishi, T. J. Med. Chem. 2000, 43, 177. https://doi.org/10.1021/jm980333v
  7. Murakami, Y.; Hara, H.; Okada, T.; Hashizume, H.; Kii, M.; Ishihara, Y.; Ishikawa, M.; Shimamura, M.; Mihara, S.-I.; Kato, G.; Hanasaki, K.; Hagishita, S.; Fujimoto, M. J. Med. Chem. 1999, 42, 2621. https://doi.org/10.1021/jm990044m
  8. Larock, R. C. Comprehensive Organic Transformations, 2nd ed.; Wiley-VCH: New York, 1999.
  9. Hashimoto, M.; Obora, Y.; Sakaguchi, S.; Ishii, Y. J. Org. Chem. 2008, 73, 2894. https://doi.org/10.1021/jo702277g
  10. Lang, S.; Murphy, J. A. Chem. Soc. Rev. 2006, 35, 146. https://doi.org/10.1039/b505080d
  11. Stecko, S.; Mames, A.; Furman, B.; Chmielewski, M. J. Org. Chem. 2009, 74, 3094. https://doi.org/10.1021/jo900121x
  12. Marco-Contelles, J. Angew. Chem. Int. Ed. 2004, 43, 2198. https://doi.org/10.1002/anie.200301730
  13. Benedek, G.; Palkio, M.; Weber, E.; Martinek, T. A.; Forro, E.; Fuliop, F. Eur. J. Org. Chem. 2008, 3724.
  14. Dam, J. H.; Osztrovszky, G.; Nordstrøm, L. U.; Madsen, R. Chem. Eur. J. 2010, 16, 6820. https://doi.org/10.1002/chem.201000569
  15. Ghosh, S. C.; Muthaiah, S.; Zhang, Y.; Xu, X.; Hong, S. H. Adv. Synth. Catal. 2009, 351, 2643. https://doi.org/10.1002/adsc.200900482
  16. Fujita, K.-i.; Takahashi, Y.; Owaki, M.; Yamamoto, K.; Yamaguchi, R. Org. Lett. 2004, 6, 2785. https://doi.org/10.1021/ol0489954
  17. Shen, M.; Li, C. J. Org. Chem. 2004, 69, 7906. https://doi.org/10.1021/jo0488006
  18. Kohn, M.; Breinbauer, R. Angew. Chem. Int. Ed. 2004, 43, 3106. https://doi.org/10.1002/anie.200401744
  19. Lee, S.-J.; Youn, S.-H.; Cho, C.-W. Org. Biomol. Chem. 2011, 9, 7734. https://doi.org/10.1039/c1ob06078c
  20. Palacios, F.; Alonso, C.; Aparicio, D.; Rubiales, G.; de los Santos, J. M. Tetrahedron 2007, 63, 523. https://doi.org/10.1016/j.tet.2006.09.048
  21. Fresneda, P. M.; Molina, P. Synlett 2004, 1.
  22. Staudinger, H.; Meyer, J. Helv. Chim. Acta 1919, 2, 635. https://doi.org/10.1002/hlca.19190020164
  23. Yoshimitsu, T.; Ino, T.; Tanaka, T. Org. Lett. 2008, 10, 5457. https://doi.org/10.1021/ol802225g
  24. Kopka, I. E.; Lin, L. S.; Jewell, J. P.; Lanza, T. J.; Fong, T. M.; Shen, C.-P.; Lao, Z. J.; Ha, S.; Castonguay, L. G.; der Ploeg, L. V.; Goulet, M. T.; Hagmann, W. K. Bioorg. Med. Chem. Lett. 2010, 20, 4757. https://doi.org/10.1016/j.bmcl.2010.06.127
  25. Perrin, C. L.; Arrhenius, G. M. L. J. Am. Chem. Soc. 1982, 104, 2839. https://doi.org/10.1021/ja00374a024
  26. Ren, W.; Yamane, M. J. Org. Chem. 2009, 74, 8332. https://doi.org/10.1021/jo901486z
  27. Padwa, A.; Hertzog, D. L.; Nadler, W. R.; Osterhout, M. H.; Price, A. T. J. Org. Chem. 1994, 59, 1418. https://doi.org/10.1021/jo00085a035
  28. Abe, M.; Akiyama, T.; Nakamura, H.; Kojima, F.; Harada, S.; Muraoka, Y. J. Nat. Prod. 2004, 67, 999. https://doi.org/10.1021/np030491b
  29. Pfeil, E.; Harder, U. Angew. Chem. Int. Ed. 1967, 6, 178.
  30. Lopez-Cobenas, A.; Cledera, P.; Sanchez, J. D.; Lopez-Alvarado, P.; Ramos, M. T.; Avendano, C.; Menendez, J. C. Synthesis 2005, 3412.

피인용 문헌

  1. SnH-Mediated Reductive Cyclization of Azido Amides vol.33, pp.2, 2012, https://doi.org/10.5012/bkcs.2012.33.2.739
  2. Recent Advances in Synthesis of 3,4‐Dihydroisoquinolin‐1(2 H )‐one vol.5, pp.27, 2012, https://doi.org/10.1002/slct.202002131