Bulletin of the Korean Chemical Society

  • 제27권8호
  • /
  • Pages.1133-1139
  • /
  • 2006
  • /
  • 0253-2964(pISSN)
  • /
  • 1229-5949(eISSN)
대한화학회 (Korean Chemical Society)
권호 표지
DOI QR코드

DOI QR Code

Synthesis of 3-Aryl-3-hydroxypyrrolidin-2-ones and 2-Benzyl-9b-hydroxy-3,3a,5,9b-tetrahydro-2H-pyrrolo[3,4-c]quinoline-1,4-dione Derivatives from the Baylis-Hillman Adducts of Isatins

  • Kim, Seung Chan (Department of Chemistry and Institute of Basic Science, Chonnam National University) ;
  • Lee, Ka Young (Department of Chemistry and Institute of Basic Science, Chonnam National University) ;
  • Gowrisankar, Saravanan (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)
  • 발행 : 2006.08.20
PDF 다운로드
⟨ 이전 논문 다음 논문 ⟩

초록

We prepared 3-aryl-3-hydroxypyrrolidin-2-one and tricyclic 2-benzyl-9b-hydroxy-3,3a,5,9b-tetrahydro-2H-pyrrolo[3,4-c]quinoline-1,4-dione derivatives starting from the Baylis-Hillman adducts of isatin derivatives.

키워드

참고문헌

  1. Choi, M. K.-W.; Yu, W.-Y.; Che, C.-M. Org. Lett. 2005, 7, 1081 https://doi.org/10.1021/ol050003m
  2. Yee, N. K.; Dong, Y.; Kapadia, S. R.; Song, J. J. J. Org. Chem. 2002, 67, 8688 https://doi.org/10.1021/jo020433f
  3. Kagoshima, H.; Okamura, T.; Akiyama, T. J. Am. Chem. Soc. 2001, 123, 7182 https://doi.org/10.1021/ja015866z
  4. Singh, V.; Saxena, R.; Batra, S. J. Org. Chem. 2005, 70, 353 https://doi.org/10.1021/jo048411b
  5. Gagosz, F.; Moutrille, C.; Zard, S. Z. Org. Lett. 2002, 4, 2707 https://doi.org/10.1021/ol026221m
  6. Elworthy, T. R.; Brill, E. R.; Chiou, S.-S.; Chu, F.; Harris, J. R.; Hendricks, R. T.; Huang, J.; Kim, W.; Lach, L. K.; Mirzadegan, T.; Yee, C.; Walker, K. A. M. J. Med. Chem. 2004, 47, 6124 https://doi.org/10.1021/jm049290a
  7. Bower, J. F.; Svenda, J.; Williams, A. J.; Charmant, J. P. H.; Lawrence, R. M.; Szeto, P.; Gallagher, T. Org. Lett. 2004, 6, 4727 https://doi.org/10.1021/ol048036+
  8. Puschl, A.; Boesen, T.; Zuccarello, G.; Dahl, O.; Pitsch, S.; Nielsen, P. E. J. Org. Chem. 2001, 66, 707 https://doi.org/10.1021/jo001000k
  9. Brabandt, W. V.; De Kimpe, N. J. Org. Chem. 2005, 70, 3369 https://doi.org/10.1021/jo048158f
  10. Serna, S.; Tellitu, I.; Dominguez, E.; Moreno, I.; SanMartin, R. Org. Lett. 2005, 7, 3073 https://doi.org/10.1021/ol0510623
  11. Othman, R. B.; Bousquet, T.; Fousse, A.; Othman, M.; Dalla, V. Org. Lett. 2005, 7, 2825 https://doi.org/10.1021/ol050576z
  12. Taylor, E. C.; Liu, B. J. Org. Chem. 2001, 66, 3726 https://doi.org/10.1021/jo001580l
  13. Cossy, J.; Madaci, A.; Pete, J.-P. Tetrahedron Lett. 1994, 35, 1541 https://doi.org/10.1016/S0040-4039(00)76753-0
  14. Calderari, G.; Seebach, D. Helv. Chim. Acta 1985, 68, 1592 https://doi.org/10.1002/hlca.19850680611
  15. Blay, G.; Fernandez, I.; Monje, B.; Pedro, J. R. Tetrahedron 2004, 60, 165 https://doi.org/10.1016/j.tet.2003.10.081
  16. Galeazzi, R.; Geremia, S.; Mobbili, G.; Orena, M. Tetrahedron: Asymmetry 1996, 7, 3573 https://doi.org/10.1016/S0957-4166(96)00466-1
  17. Galeazzi, R.; Mobbili, G.; Orena, M. Tetrahedron 1999, 55, 4029 https://doi.org/10.1016/S0040-4020(99)00091-5
  18. Galeazzi, R.; Mobbili, G.; Orena, M. Tetrahedron 1999, 55, 261 https://doi.org/10.1016/S0040-4020(98)01031-X
  19. Galeazzi, R.; Mobbili, G.; Orena, M. Tetrahedron: Asymmetry 1997, 8, 133 https://doi.org/10.1016/S0957-4166(96)00477-6
  20. Fava, C.; Galeazzi, R.; Mobbili, G.; Orena, M. Tetrahedron: Asymmetry 2003, 14, 3697 https://doi.org/10.1016/j.tetasy.2003.08.024
  21. Galeazzi, R.; Martelli, G.; Mobbili, G.; Orena, M.; Rinaldi, S. Tetrahedron: Asymmetry 2003, 14, 3353 https://doi.org/10.1016/S0957-4166(03)00599-8
  22. Galeazzi, R.; Mobbili, G.; Orena, M. Tetrahedron 1996, 52, 1069 https://doi.org/10.1016/0040-4020(95)00939-6
  23. Galeazzi, R.; Geremia, S.; Mobbili, G.; Orena, M. Tetrahedron: Asymmetry 1996, 7, 79 https://doi.org/10.1016/0957-4166(95)00423-8
  24. Synthesis of natural chimonamidine, Takayama, H.; Matsuda, Y.; Masubuchi, K.; Ishida, A.; Kitajima, M.; Aimi, N. Tetrahedron 2004, 60, 893 https://doi.org/10.1016/j.tet.2003.11.034
  25. Amri, H.; El Gaied, M. M.; Ben Ayed, T.; Villieras, J. Tetrahedron Lett. 1992, 33, 7345 https://doi.org/10.1016/S0040-4039(00)60183-1
  26. Galeazzi, R.; Martelli, G.; Mobbili, G.; Orena, M.; Rinaldi, S. Tetrahedron: Asymmetry 2004, 15, 3249 https://doi.org/10.1016/j.tetasy.2004.08.016
  27. Ben Ayed, T.; Amri, H.; El Gaied, M. M.; Villieras, J. Tetrahedron 1995, 51, 9633 https://doi.org/10.1016/0040-4020(95)00538-J
  28. Beltaief, I.; Besbes, R.; Ben Amor, F.; Amri, H.; Villieras, M.; Villieras, J. Tetrahedron 1999, 55, 3949 https://doi.org/10.1016/S0040-4020(99)00118-0
  29. Basavaiah, D.; Sreenivasulu, B.; Rao, A. L. J. Org. Chem. 2003, 68, 5983 https://doi.org/10.1021/jo0342424
  30. Basavaiah, D.; Bharati, T. K.; Gowriswari, V. V. L. Tetrahedron Lett. 1987, 28, 4351 https://doi.org/10.1016/S0040-4039(00)96506-7
  31. Khuzhaev, V. U. Chemistry of Natural Compounds 2004, 40, 516 https://doi.org/10.1007/s10600-005-0025-y
  32. Khuzhaev, V. U.; Tashkhodzhaev, B.; Aripova, S. F. Khim. Prir. Soedin. 1995, 720
  33. Rasmussen, H. B.; MacLeod, J. K. J. Nat. Prod. 1997, 60, 1152 https://doi.org/10.1021/np970246q
  34. Kawasaki, T.; Nagaoka, M.; Satoh, T.; Okamoto, A.; Ukon, R.; Ogawa, A. Tetrahedron 2004, 60, 3493 https://doi.org/10.1016/j.tet.2004.02.031
  35. Inoue, M.; Sakazaki, H.; Furuyama, H.; Hirama, M. Angew. Chem. Int. Ed. 2003, 42, 2654 https://doi.org/10.1002/anie.200351130
  36. 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
  37. Lee, K. Y.; Lee, C. G.; Na, J. E.; Kim, J. N. Tetrahedron Lett. 2005, 46, 69 https://doi.org/10.1016/j.tetlet.2004.11.046
  38. 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
  39. Gowrisankar, S.; Lee, K. Y.; Kim, J. N. Tetrahedron Lett. 2005, 46, 4859 https://doi.org/10.1016/j.tetlet.2005.05.057
  40. Lee, K. Y.; Gowrisankar, S.; Kim, J. N. Tetrahedron Lett. 2005, 46, 5387 https://doi.org/10.1016/j.tetlet.2005.05.149
  41. Park, D. Y.; Lee, M. J.; Kim, T. H.; Kim, J. N. Tetrahedron Lett. 2005, 46, 8799 https://doi.org/10.1016/j.tetlet.2005.10.034
  42. Lee, K. Y.; Kim, S. C.; Kim, J. N. Tetrahedron Lett. 2006, 47, 977 https://doi.org/10.1016/j.tetlet.2005.11.142
  43. Lee, M. J.; Lee, K. Y.; Gowrisankar, S.; Kim, J. N. Tetrahedron Lett. 2006, 47, 1355 https://doi.org/10.1016/j.tetlet.2005.12.032
  44. Chung, Y. M.; Im, Y. J.; Kim, J. N. Bull. Korean Chem. Soc. 2002, 23, 1651 https://doi.org/10.5012/bkcs.2002.23.11.1651
  45. Garden, S. J.; Skakle, J. M. S. Tetrahedron Lett. 2002, 43, 1969 https://doi.org/10.1016/S0040-4039(02)00160-0
  46. Perlmutter, P.; Tabone, M. Tetrahedron Lett. 1988, 29, 949 https://doi.org/10.1016/S0040-4039(00)82490-9
  47. Tetrahedron Lett. 2006, 47, 3463 https://doi.org/10.1016/j.tetlet.2006.03.074
  48. Kravchenko, D. V.; Kuzovkova, Y. A.; Kysil, V. M.; Tkachenko, S. E.; Maliarchouk, S.; Okun, I. M.; Balakin, K. V.; Ivachtchenko, A. V. J. Med. Chem. 2005, 48, 3680 https://doi.org/10.1021/jm048987t
  49. Cappelli, A.; Anzini, M.; Vomero, S.; Mennuni, L.; Makovec, F.; Doucet, E.; Hamon, M.; Menziani, M. C.; De Benedetti, P. G.; Giorgi, G.; Ghelardini, C.; Collina, S. Bioorg. Med. Chem. 2002, 10, 779 https://doi.org/10.1016/S0968-0896(01)00332-7
  50. Molina, P.; Arques, A.; Alias, A.; Vinader, M. V. Tetrahedron Lett. 1991, 32, 4401 https://doi.org/10.1016/S0040-4039(00)92181-6
  51. Bailey, P. D.; Cochrane, P. J.; Irvine, F.; Morgan, K. M.; Pearson, D. P. J.; Veal, K. T. Tetrahedron Lett. 1999, 40, 4593 https://doi.org/10.1016/S0040-4039(99)00692-9
  52. Molina, P.; Arques, A.; Alias, A.; Vinader, M. V. Tetrahedron 1992, 48, 3091 https://doi.org/10.1016/S0040-4020(01)92251-3

피인용 문헌

  1. Recent Advances in Construction of Nitrogen-containing Heterocycles from Baylis-Hillman Adducts vol.43, pp.1, 2011, https://doi.org/10.1080/00304948.2011.549065
  2. Facile Synthesis of 5-Alkylidene-1,5-dihydropyrrol-2-ones from Morita-Baylis-Hillman Adducts vol.33, pp.4, 2012, https://doi.org/10.5012/bkcs.2012.33.4.1337
  3. Synthesis of Lactams by Isomerization of Oxindoles Substituted at C-3 by an ω-Amino Chain vol.79, pp.22, 2014, https://doi.org/10.1021/jo501978j
  4. ]quinolines from Morita-Baylis-Hillman Adducts of 2-Bromobenzaldehydes vol.36, pp.1, 2015, https://doi.org/10.1002/bkcs.10050
  5. ]quinoline-1,2-diones via Intramolecular Friedel-Crafts Cyclization Protocol vol.36, pp.11, 2015, https://doi.org/10.1002/bkcs.10539
  6. ) – mediated regioselective β-cross-coupling aldol type addition reaction of activated alkenes with isatins/isatinimines in aqueous media vol.5, pp.64, 2015, https://doi.org/10.1039/C5RA07216F
  7. ) – catalyzed α-cross-coupling aldol type addition reaction of activated olefins with isatins vol.6, pp.3, 2016, https://doi.org/10.1039/C5RA14714J
  8. Synthesis of 3-Aryl-3-hydroxypyrrolidin-2-ones and 2-Benzyl-9b-hydroxy-3,3a,5,9b-tetrahydro-2H-pyrrolo [3,4-c]quinoline-1,4-dione Derivatives from the Baylis—Hillman Adducts of Isatins. vol.38, pp.1, 2007, https://doi.org/10.1002/chin.200701040
  9. Facile Synthesis of 1,2,3,4-Tetrasubstituted Pyrroles from Baylis-Hillman Adducts vol.28, pp.9, 2006, https://doi.org/10.5012/bkcs.2007.28.9.1605
  10. Construction of Chiral Quaternary Carbon through Morita–Baylis–Hillman Reaction: An Enantioselective Approach to 3‐Substituted 3‐Hydroxyoxindole Derivatives vol.16, pp.46, 2006, https://doi.org/10.1002/chem.201002240
  11. An Efficient Five‐Component Reaction for the Synthesis of 4,4′‐((2‐Oxoindoline‐3,3‐diyl)bis(methylene))bis(2‐aryl‐1 H ‐pyrrolo[3,4‐ vol.56, pp.8, 2019, https://doi.org/10.1002/jhet.3592