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Facile Synthesis of 5-Alkylidene-1,5-dihydropyrrol-2-ones from Morita-Baylis-Hillman Adducts

  • Park, Bo-Ram (Department of Chemistry and Institute of Basic Science, Chonnam National University) ;
  • Lim, Cheol-Hee (Department of Chemistry and Institute of Basic Science, Chonnam National University) ;
  • Lim, Jin-Woo (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 : 2011.12.05
  • Accepted : 2011.12.27
  • Published : 2012.04.20

Abstract

Keywords

References

  1. Anders, J. T.; Gorls, H.; Langer, P. Eur. J. Org. Chem. 2004, 1897-1910 https://doi.org/10.1002/ejoc.200300727
  2. Rico, R.; Bermejo, F. Tetrahedron Lett. 1996, 37, 5809-5812. https://doi.org/10.1016/0040-4039(96)01232-4
  3. Bermejo, F. A.; Rico-Ferreira, R. J. Org. Chem. 2001, 66, 8287- 8292. https://doi.org/10.1021/jo010527+
  4. Felluga, F.; Ghelfi, F.; Pagnoni, U. M.; Parsons, A. F.; Pattarozzi, M.; Roncaglia, F.; Valentin, E. Synthesis 2007, 1882- 1886.
  5. Bessho, J.-I.; Shimotsu, Y.; Mizumoto, S.; Mase, N.; Yoda, H.; Takabe, K. Heterocycles 2004, 63, 1013-1016. https://doi.org/10.3987/COM-04-10030
  6. Li, W.-R.; Lin, S. T.; Hsu, N.-M.; Chern, M.-S. J. Org. Chem. 2002, 67, 4702-4706. https://doi.org/10.1021/jo010828j
  7. Coperet, C.; Sugihara, T.; Wu, G.; Shimoyama, I.; Negishi, E.-I. J. Am. Chem. Soc. 1995, 117, 3422-3431. https://doi.org/10.1021/ja00117a011
  8. Haase, C.; Langer, P. Tetrahedron 2009, 65, 4530-4539. https://doi.org/10.1016/j.tet.2009.03.102
  9. Mykhaylychenko, S.; Harakat, D.; Dupas, G.; Shermolovich, Y. G.; Bouillon, J.-P. J. Fluorine Chem. 2009, 130, 418-427. https://doi.org/10.1016/j.jfluchem.2009.01.008
  10. Ngwe, H.; Kinoshita, H.; Inomata, K. Bull. Chem. Soc. Jpn. 1994, 67, 3320-3326. https://doi.org/10.1246/bcsj.67.3320
  11. Kinoshita, H.; Ngwe, H.; Kobori, K.; Inomata, K. Chem. Lett. 1993, 1441-1442.
  12. Ma, S.; Xie, H. Org. Lett. 2000, 2, 3801-3803.
  13. Boukouvalas, J; Loach, R. P.; Ouellet, E. Tetrahedron Lett. 2011, 52, 5047-5050 https://doi.org/10.1016/j.tetlet.2011.07.084
  14. Watson, A. F.; Liu, J.; Bennaceur, K.; Drummond, C. J.; Endicott, J. A.; Golding, B. T.; Griffin, R. J.; Haggerty, K.; Lu, X.; McDonnell, J. M.; Newell, D. R.; Noble, M. E. M.; Revill, C. H.; Riedinger, C.; Xu, Q.; Zhao, Y.; Lunec, J.; Hardcastle, I. R. Bioorg. Med. Chem. Lett. 2011, 21, 5916-5919.
  15. Basavaiah, D.; Rao, A. J.; Satyanarayana, T. Chem. Rev. 2003, 103, 811-891. https://doi.org/10.1021/cr010043d
  16. Basavaiah, D.; Reddy, B. S.; Badsara, S. S. Chem. Rev. 2010, 110, 5447-5674. https://doi.org/10.1021/cr900291g
  17. Singh, V.; Batra, S. Tetrahedron 2008, 64, 4511-4574. https://doi.org/10.1016/j.tet.2008.02.087
  18. Declerck, V.; Martinez, J.; Lamaty, F. Chem. Rev. 2009, 109, 1-48. https://doi.org/10.1021/cr068057c
  19. Ciganek, E. In Organic Reactions; Paquette, L. A., Ed.; John Wiley & Sons: New York, 1997; Vol. 51, pp 201-350.
  20. Kim, J. N.; Lee, K. Y. Curr. Org. Chem. 2002, 6, 627-645. https://doi.org/10.2174/1385272023374094
  21. Lee, K. Y.; Gowrisankar, S.; Kim, J. N. Bull. Korean Chem. Soc. 2005, 26, 1481-1490. https://doi.org/10.5012/bkcs.2005.26.10.1481
  22. Radha Krishna, P.; Sachwani, R.; Reddy, P. S. Synlett 2008, 2897- 2912.
  23. Gowrisankar, S.; Lee, H. S.; Kim, S. H.; Lee, K. Y.; Kim, J. N. Tetrahedron 2009, 65, 8769-8780. https://doi.org/10.1016/j.tet.2009.07.034
  24. Lee, K. Y.; Lee, Y. J.; Kim, J. N. Bull. Korean Chem. Soc. 2007, 28, 143-146. https://doi.org/10.5012/bkcs.2007.28.1.143
  25. Kim, S. C.; Gowrisankar, S.; Kim, J. N. Tetrahedron Lett. 2006, 47, 3463-3466. https://doi.org/10.1016/j.tetlet.2006.03.074
  26. Kim, S. C.; Lee, K. Y.; Gowrisankar, S.; Kim, J. N. Bull. Korean Chem. Soc. 2006, 27, 1133-1139. https://doi.org/10.5012/bkcs.2006.27.8.1133
  27. Lee, H. S.; Kim, S. J.; Kim, J. N. Bull. Korean Chem. Soc. 2006, 27, 1063-1066. https://doi.org/10.5012/bkcs.2006.27.7.1063
  28. Lee, M. J.; Lee, K. Y.; Park, D. Y.; Kim, J. N. Bull. Korean Chem. Soc. 2005, 26, 1281-1285. https://doi.org/10.5012/bkcs.2005.26.8.1281
  29. Amri, H.; El Gaied, M. M.; Ben Ayed, T.; Villieras, J. Tetrahedron Lett. 1992, 33, 6159-6160. https://doi.org/10.1016/S0040-4039(00)60031-X
  30. Buchholz, R.; Hoffmann, H. M. R. Helv. Chim. Acta 1991, 74, 1213-1220. https://doi.org/10.1002/hlca.19910740608
  31. Singh, V.; Saxena, R.; Batra, S. J. Org. Chem. 2005, 70, 353- 356. https://doi.org/10.1021/jo048411b
  32. Singh, V.; Yadav, G. P.; Maulik, P. R.; Batra, S. Tetrahedron 2008, 64, 2979-2991. https://doi.org/10.1016/j.tet.2008.01.074
  33. Singh, V.; Yadav, G. P.; Maulik, P. R.; Batra, S. Tetrahedron 2006, 62, 8731-8739. https://doi.org/10.1016/j.tet.2006.06.099
  34. Coelho, F.; Diaz, G.; Abella, C. A. M.; Almeida, W. P. Synlett 2006, 435-439.
  35. Basavaiah, D.; Rao, J. S. Tetrahedron Lett. 2004, 45, 1621- 1625. https://doi.org/10.1016/j.tetlet.2003.12.133
  36. Ramachandran, P. V.; Madhi, S.; Bland-Berry, L.; Reddy, M. V. R.; O'Donnell, M. J. J. Am. Chem. Soc. 2005, 127, 13450- 13451. https://doi.org/10.1021/ja052638m
  37. Kawahara, S.; Nakano, A.; Esumi, T.; Iwabuchi, Y.; Hatakeyama, S. Org. Lett. 2003, 5, 3103-3105. https://doi.org/10.1021/ol035102j
  38. Song, Y. S.; Lee, C. H.; Lee, K.-J. J. Heterocyclic Chem. 2003, 40, 939-941. https://doi.org/10.1002/jhet.5570400532
  39. Park, B. R.; Kim, K. H.; Lim, J. W.; Kim, J. N. Tetrahedron Lett. 2012, 53, 36-40. https://doi.org/10.1016/j.tetlet.2011.11.001
  40. Abell, A. D.; Oldham, M. D.; Taylor, J. M. J. Org. Chem. 1995, 60, 1214-1220. https://doi.org/10.1021/jo00110a026
  41. Beck, J. J.; Stermitz, F. R. J. Nat. Prod. 1995, 58, 1047-1055. https://doi.org/10.1021/np50121a009
  42. Tripathi, R. P.; Dwivedi, N.; Singh, N.; Misra, M. Med. Chem. Res. 2008, 17, 53-61. https://doi.org/10.1007/s00044-007-9036-5
  43. Goh, W. K.; Black, D. StC.; Kumar, N. Tetrahedron Lett. 2007, 48, 9008-9011. https://doi.org/10.1016/j.tetlet.2007.10.093
  44. Goh, W. K.; Iskander, G.; Black, D. StC.; Kumar, N. Tetrahedron Lett. 2007, 48, 2287-2290. https://doi.org/10.1016/j.tetlet.2007.01.165

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