Bulletin of the Korean Chemical Society

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Synthesis of 3-Benzyl- or 3-Benzoyl-7,8-dihydro-6H-chromene Derivatives Starting from Baylis-Hillman Adducts

  • Kim, Seung-Chan (Department of Chemistry and Institute of Basic Science, Chonnam National University) ;
  • Lee, Hyun-Seung (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)
  • Published : 2007.01.20
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References

  1. Basavaiah, D.; Jaganmohan, R.; Satyanarayana, T. Chem. Rev. 2003, 103, 811 https://doi.org/10.1021/cr010043d
  2. 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
  3. Kim, J. N.; Lee, K. Y. Curr. Org. Chem. 2002, 6, 627 https://doi.org/10.2174/1385272023374094
  4. Chamakh, A.; Amri, H. Tetrahedron Lett. 1998, 39, 375 https://doi.org/10.1016/S0040-4039(97)10593-7
  5. Kim, J. N.; Im, Y. J.; Kim, J. M. Tetrahedron Lett. 2002, 43, 6597 https://doi.org/10.1016/S0040-4039(02)01441-7
  6. Kim, J. N.; Kim, J. M.; Lee, K. Y.; Gowrisankar, S. Bull. Korean Chem. Soc. 2004, 25, 1733 https://doi.org/10.5012/bkcs.2004.25.11.1733
  7. Kim, J. N.; Kim, J. M.; Lee, K. Y. Synlett 2003, 821
  8. Im, Y. J.; Lee, C. G.; Kim, H. R.; Kim, J. N. Tetrahedron Lett. 2003, 44, 2987 https://doi.org/10.1016/S0040-4039(03)00397-6
  9. Kim, J. M.; Lee, K. Y.; Kim, J. N. Bull. Korean Chem. Soc. 2004, 25, 328 https://doi.org/10.5012/bkcs.2004.25.2.328
  10. Gowrisankar, S.; Na, J. E.; Lee, M. J.; Kim, J. N. Bull. Korean Chem. Soc. 2005, 26, 319 https://doi.org/10.5012/bkcs.2005.26.2.319
  11. Chyu, C.-F.; Chiang, Y.-M.; Lin, H.-C.; Kuo, Y.-H. Tetrahedron Lett. 2004, 45, 641 https://doi.org/10.1016/j.tetlet.2003.07.008
  12. Afarinkia, K.; Posner, G. H. Tetrahedron Lett. 1992, 33, 7839 https://doi.org/10.1016/S0040-4039(00)74757-5
  13. Hsung, R. P.; Shen, H. C.; Douglas, C. J.; Morgan, C. D.; Degen, S. J.; Yao, L. J. J. Org. Chem. 1999, 64, 690 https://doi.org/10.1021/jo982165k
  14. Chen, C.-H.; Liao, C.-C. Org. Lett. 2000, 2, 2049
  15. Schlingmann, G.; Milne, L.; Carter, G. T. Tetrahedron 1998, 54, 13013 https://doi.org/10.1016/S0040-4020(98)00792-3
  16. Shi, X.; Leal, W. S.; Liu, Z.; Schrader, E.; Meinwald, J. Tetrahedron Lett. 1995, 36, 71 https://doi.org/10.1016/0040-4039(94)02214-V
  17. Gehrt, A.; Erkel, G.; Anke, T.; Sterner, O. Z. Naturforsch 1997, 53c, 89
  18. Trummer, I.; Ziegler, E.; Wolfbeis, O. S. Synthesis 1981, 225
  19. Bohme, H.; Gratz, J. G. V. Tetrahedron 1977, 33, 841 https://doi.org/10.1016/0040-4020(77)80031-8
  20. Kotretsou, S. I.; Georgiadis, M. P. Org. Prep. Proceed. Int. 2000, 32, 161 https://doi.org/10.1080/00304940009356281
  21. Stanovnik, B. J. Heterocyclic Chem. 1999, 36, 1581 https://doi.org/10.1002/jhet.5570360619
  22. Kepe, V.; Polanc, S.; Kocevar, M. Heterocycles 1998, 48, 671 https://doi.org/10.3987/COM-97-8048
  23. Larock, R. C.; Doty, M. J.; Han, X. J. Org. Chem. 1999, 64, 8770 https://doi.org/10.1021/jo9821628
  24. Larock, R. C.; Han, X.; Doty, M. J. Tetrahedron Lett. 1998, 39, 5713 https://doi.org/10.1016/S0040-4039(98)01182-4
  25. Cerezo, S.; Moreno-Manas, M.; Pleixats, R. Tetrahedron 1998, 54, 7813
  26. Yao, T.; Larock, R. C. J. Org. Chem. 2003, 68, 5936 https://doi.org/10.1021/jo034308v
  27. Ma, S.; Yu, S.; Yin, S. J. Org. Chem. 2003, 68, 8996 https://doi.org/10.1021/jo034633i
  28. Zhu, X.-F.; Schaffner, A.-P.; Li, R. C.; Kwon, O. Org. Lett. 2005, 7, 2977 https://doi.org/10.1021/ol050946j
  29. Bellina, F.; Biagetti, M.; Carpita, A.; Rossi, R. Tetrahedron 2001, 57, 2857 https://doi.org/10.1016/S0040-4020(01)00139-9
  30. Bellina, F.; Biagetti, M.; Carpita, A.; Rossi, R. Tetrahedron Lett. 2001, 42, 2859 https://doi.org/10.1016/S0040-4039(01)00290-8
  31. Ma, S.; Yin, S.; Li, L.; Tao, F. Org. Lett. 2002, 4, 505 https://doi.org/10.1021/ol0170859
  32. Biagetti, M.; Bellina, F.; Carpita, A.; Stabile, P.; Rossi, R. Tetrahedron 2002, 58, 5023 https://doi.org/10.1016/S0040-4020(02)00469-6
  33. Dauben, W. G.; Lorber, M.; Fullerton, D. S. J. Org. Chem. 1969, 34, 3587 https://doi.org/10.1021/jo01263a079
  34. Parish, E. J.; Chitrakorn, S.; Wei, T.-Y. Synth. Commun. 1986, 16, 1371
  35. Parish, E. J.; Wei, T.-Y. Synth. Commun. 1987, 17, 1227
  36. Fernandes, R. A.; Kumar, P. Tetrahedron Lett. 2003, 44, 1275 https://doi.org/10.1016/S0040-4039(02)02784-3
  37. Cuellar, M. A.; Moreno, L. E.; Preite, M. D. Arkivoc 2003 (x), 169
  38. Page, P. C. B.; McCarthy, T. J. In Comprehensive Organic Synthesis; Trost, B. M.; Fleming, I., Eds.; Pergamon Press: Oxford, 1991; Vol. 7, pp 99-113

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