DOI QR코드

DOI QR Code

Synthesis of Arene-Fused Isoindoline Derivatives from Morita-Baylis-Hillman Adducts by IMDA Reaction Using Z-Vinylarenes as 1,3-Dienes

  • Kim, Ko Hoon (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) ;
  • Moon, Hye Ran (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)
  • 투고 : 2014.07.01
  • 심사 : 2014.07.21
  • 발행 : 2014.11.20

초록

Intramolecular Diels-Alder (IMDA) reaction of vinylarenes bearing a Z-alkenyl tether, prepared from Morita-Baylis-Hillman (MBH) adducts, afforded arene-fused isoindoline derivatives in good yields. Vinylfurans, vinylthiophenes, and vinylnaphthalenes could be used successfully as dienes, while vinylbenzene failed under the same reaction conditions.

키워드

참고문헌

  1. (a) Kolis, S. P.; Chordia, M. D.; Liu, R.; Kopach, M. E.; Harman, W. D. J. Am. Chem. Soc. 1998, 120, 2218-2226. https://doi.org/10.1021/ja973700l
  2. (b) Stranix, B. R.; Darling, G. D. J. Org. Chem. 1997, 62, 9001-9004. https://doi.org/10.1021/jo961649i
  3. (c) Carreno, M. C.; Mahugo, J.; Urbano, A. Tetrahedron Lett. 1997, 38, 3047-3050. https://doi.org/10.1016/S0040-4039(97)00505-4
  4. (d) Willmore, N. D.; Hoic, D. A.; Katz, T. J. J. Org. Chem. 1994, 59, 1889-1891. https://doi.org/10.1021/jo00086a046
  5. (a) Drew, M. G. B.; Jahans, A.; Harwood, L. M.; Apoux, S. A. B. H. Eur. J. Org. Chem. 2002, 3589-3594.
  6. (b) Kotsuki, H.; Kondo, A.; Nishizawa, H.; Ochi, M.; Matsuoka, K. J. Org. Chem. 1981, 46, 5454-5455. https://doi.org/10.1021/jo00339a055
  7. (c) Marrocchi, A.; Minuti, L.; Taticchi, A.; Scheeren, H. W. Tetrahedron 2001, 57, 4959- 4965. https://doi.org/10.1016/S0040-4020(01)00406-9
  8. (d) Bodalski, R.; Koszuk, J.; Krawczyk, H.; Pietrusiewicz, K. M. J. Org. Chem. 1982, 47, 2219-2220. https://doi.org/10.1021/jo00132a057
  9. (a) Pedrosa, R.; Andres, C.; Nieto, J. J. Org. Chem. 2002, 67, 782-789. https://doi.org/10.1021/jo010746v
  10. (b) Sun, S.; Turchi, I. J.; Xu, D.; Murray, W. V. J. Org. Chem. 2000, 65, 2555-2559. https://doi.org/10.1021/jo991956z
  11. (c) Klemm, L. H.; McGuire, T. M.; Gopinath, K. W. J. Org. Chem. 1976, 41, 2571-2579. https://doi.org/10.1021/jo00877a014
  12. (d) Dawson, J. R.; Mellor, J. M. Tetrahedron Lett. 1995, 36, 9043-9046. https://doi.org/10.1016/0040-4039(95)01907-Y
  13. (e) Chackalamannil, S.; Doller, D.; Clasby, M.; Xia, Y.; Eagen, K.; Lin, Y.; Tsai, H.-A.; McPhail, A. T. Tetrahedron Lett. 2000, 41, 4043-4047. https://doi.org/10.1016/S0040-4039(00)00585-2
  14. (f) Kocsis, L. S.; Benedetti, E.; Brummond, K. M. Org. Lett. 2012, 14, 4430-4433. https://doi.org/10.1021/ol301938z
  15. (g) Ozawa, T.; Kurahashi, T.; Matsubara, S. Org. Lett. 2011, 13, 5390-5393. https://doi.org/10.1021/ol202283d
  16. (h) Park, J.-E.; Lee, J.; Seo, S.-Y.; Shin, D. Tetrahedron Lett. 2014, 55, 818-820. https://doi.org/10.1016/j.tetlet.2013.12.014
  17. (i) Parvatkar, P. T.; Kadam, H. K.; Tilve, S. G. Tetrahedron 2014, 70, 2857-2888 https://doi.org/10.1016/j.tet.2014.02.048
  18. (a) Uchida, T.; Rodriquez, M.; Schreiber, S. L. Org. Lett. 2009, 11, 1559-1562. https://doi.org/10.1021/ol900173t
  19. (b) Patre, R. E.; Gawas, S.; Sen, S.; Parameswaran, P. S.; Tilve, S. G. Tetrahedron Lett. 2007, 48, 3517-3520. https://doi.org/10.1016/j.tetlet.2007.03.114
  20. (c) Sun, S.; Murray, W. V. J. Org. Chem. 1999, 64, 5941-5945. https://doi.org/10.1021/jo990460e
  21. (d) Kotsuki, H.; Kawamura, A.; Ochi, M. Tokoroyama, T. Chem. Lett. 1981, 917-920.
  22. (e) Cooper, J. A.; Cornwall, P.; Dell, C. P.; Knight, D. W. Tetrahedron Lett. 1988, 29, 2107-2110. https://doi.org/10.1016/S0040-4039(00)87847-8
  23. (f) Kim, P.; Tsuruda, J. M.; Olmstead, M. M.; Eisenberg, S.; Kurth, M. J. Tetrahedron Lett. 2002, 43, 3963-3966. https://doi.org/10.1016/S0040-4039(02)00565-8
  24. (g) Madalengoitia, J. S.; Macdonald, T. L. Tetrahedron Lett. 1993, 34, 6237-6240. https://doi.org/10.1016/S0040-4039(00)73719-1
  25. (h) Torney, P.; Patre, R.; Tilve, S. Synlett 2011, 639-642.
  26. (i) He, Y.; Krishnamoorthy, P.; Lima, H. M.; Chen, Y.; Wu, H.; Sivappa, R.; Dias, H. V. R.; Lovely, C. J. Org. Biomol. Chem. 2011, 9, 2685-2701. https://doi.org/10.1039/c0ob00657b
  27. (j) He, Y.; Chen, Y.; Wu, H.; Lovely, C. J. Org. Lett. 2003, 5, 3623-3626.
  28. (k) Hayakawa, K.; Nagatsugi, F.; Kanematsu, K. J. Org. Chem. 1988, 53, 860-863. https://doi.org/10.1021/jo00239a033
  29. Kim, K. H.; Lee, S.; Lee, J.; Go, M. J.; Kim, J. N. Tetrahedron Lett. 2013, 54, 5739-5743 https://doi.org/10.1016/j.tetlet.2013.08.031
  30. (a) Hu, Y.; Song, F.; Wu, F.; Cheng, D.; Wang, S. Chem. Eur. J. 2008, 14, 3110-3117. https://doi.org/10.1002/chem.200702035
  31. (b) Hu, Y.; Ouyang, Y.; Qu, Y.; Hu, Q.; Yao, H. Chem. Commun. 2009, 4575-4577.
  32. (c) Hu, Y.; Qu, Y.; Wu, F.; Gui, J.; Wei, Y.; Hu, Q.; Wang, S. Chem. Asian J. 2010, 5, 309-314. https://doi.org/10.1002/asia.200900307
  33. (d) Ohno, H.; Miyamura, K.; Mizutani, T.; Kadoh, Y.; Takeoka, Y.; Hamaguchi, H.; Tanaka, T. Chem. Eur. J. 2005, 11, 3728-3741. https://doi.org/10.1002/chem.200500050
  34. (e) Ohno, H.; Miyamura, K.; Takeoka, Y.; Tanaka, T. Angew. Chem. Int. Ed. 2003, 42, 2647-2650. https://doi.org/10.1002/anie.200351011
  35. (a) Basavaiah, D.; Rao, A. J.; Satyanarayana, T. Chem. Rev. 2003, 103, 811-891. https://doi.org/10.1021/cr010043d
  36. (b) Basavaiah, D.; Reddy, B. S.; Badsara, S. S. Chem. Rev. 2010, 110, 5447-5674. https://doi.org/10.1021/cr900291g
  37. (c) Singh, V.; Batra, S. Tetrahedron 2008, 64, 4511-4574. https://doi.org/10.1016/j.tet.2008.02.087
  38. (d) Declerck, V.; Martinez, J.; Lamaty, F. Chem. Rev. 2009, 109, 1-48. https://doi.org/10.1021/cr068057c
  39. (e) Ciganek, E. In Organic Reactions; Paquette, L. A., Ed.; John Wiley & Sons: New York, 1997; Vol. 51, pp 201-350.
  40. (f) Kim, J. N.; Lee, K. Y. Curr. Org. Chem. 2002, 6, 627-645.
  41. (g) Lee, K. Y.; Gowrisankar, S.; Kim, J. N. Bull. Korean Chem. Soc. 2005, 26, 1481-1490.
  42. (h) 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
  43. (i) Shi, M.; Wang, F.-J.; Zhao, M.-X.; Wei, Y. The Chemistry of the Morita-Baylis-Hillman Reaction; RSC Publishing: Cambridge, UK, 2011.
  44. Howell, B. A.; Powers, J. J.; Priddy, D. B. Polym. Prepr. 2002, 43, 386-387.
  45. (a) Ding, M.; He, F.; Hudyma, T. W.; Zheng, X.; Poss, M. A.; Kadow, J. F.; Beno, B. R.; Rigat, K. L.; Wang, Y.-K.; Fridell, R. A.; Lemm, J. A.; Qiu, D.; Liu, M.; Voss, S.; Pelosi, L. A.; Roberts, S. B.; Gao, M.; Knipe, J.; Gentles, R. G. Bioorg. Med. Chem. Lett. 2012, 22, 2866-2871.
  46. (b) Fishwick, C. W. G.; Grigg, R.; Sridharan, V.; Virica, J. Tetrahedron 2003, 59, 4451-4468. https://doi.org/10.1016/S0040-4020(03)00517-9
  47. Kappe, C. O.; Murphree, S. S.; Padwa, A. Tetrahedron 1997, 53, 14179-14233 and further references cited therein. https://doi.org/10.1016/S0040-4020(97)00747-3
  48. (b) Nieto-Garcia, O.; Alonso, R. J. Org. Chem. 2013, 78, 2564-2570.
  49. (c) Chen, Y.; Wang, L.; Liu, Y.; Li, Y. Chem. Eur. J. 2011, 17, 12582-12586.
  50. (d) Liu, L.; Gao, Y.; Che, C.; Wu, N.; Wang, D. Z.; Li, C.-C.; Yang, Z. Chem. Commun. 2009, 662-664. (e) Li, C.-C.; Liang, S.; Zhang, X.-H.; Xie, Z.-X.; Chen, J.-H.; Wu, Y.-D.; Yang, Z. Org. Lett. 2005, 7, 3709-3712.
  51. Anderson, M. R.; Brown, R. F. C.; Coulston, K. J.; Eastwood, F. W.; Ward, A. Aus. J. Chem. 1990, 43, 1137-1150.
  52. (a) Matsumoto, K.; Goto, S.; Hayashi, N.; Iida, H.; Uchida, T.; Kakehi, A. Eur. J. Org. Chem. 2004, 4667-4671.
  53. (b) Doecke, C. W.; Garratt, P. J. J. Chem. Soc., Chem. Commun. 1981, 873-874.
  54. (c) Thummel, R. P. J. Chem. Soc., Chem. Commun. 1974, 899-900.
  55. (a) Hu, Y.-M.; Lim, X.-G.; Zhu, T.; Wan, J.; Sun, Y.-J.; Zhao, Q.-S.; Yu, T. Synthesis 2010, 3467-3473.
  56. (b) Shibata, T.; Fujiwara, R.; Takano, D. Synlett 2005, 2062-2066.
  57. (c) Rodriguez, D.; Navarro-Vazquez, A. Castedo, L.; Dominguez, D.; Saa, C. J. Am. Chem. Soc. 2001, 123, 9178-9179.

피인용 문헌

  1. ]azepines from Morita-Baylis-Hillman Adducts via Pictet-Spengler Reaction vol.37, pp.5, 2016, https://doi.org/10.1002/bkcs.10752