DOI QR코드

DOI QR Code

One-Pot Cascade Michael-Cyclization Reactions of o-Hydroxycinnamaldehydes: Synthesis of Functionalized 2,3-Dihydrobenzofuranes

  • Gwon, Sung-Hyuk (Department of Chemistry, College of Natural Science, Kyonggi University) ;
  • Kim, Sung-Gon (Department of Chemistry, College of Natural Science, Kyonggi University)
  • Received : 2012.04.10
  • Accepted : 2012.05.10
  • Published : 2012.08.20

Abstract

Keywords

References

  1. Bertolini, F.; Pineschni, M. Org. Pre. Proced. Int. 2009, 41, 385. https://doi.org/10.1080/00304940903240836
  2. Bose, J. S.; Gangan, V.; Prakash, R.; Jain, S. K.; Manna, S. K. J. Med. Chem. 2009, 52, 3184. https://doi.org/10.1021/jm8015766
  3. Yamaguchi, S.; Muro, S.; Kobayashi, M.; Miyazawa, M.; Hirai, Y. J. Org. Chem. 2003, 68, 6274. https://doi.org/10.1021/jo034396j
  4. Chen, C.-H.; Shaw, C.-Y.; Chen, C.-C.; Tsai, Y.-C. J. Nat. Prod. 2002, 65, 740. https://doi.org/10.1021/np010605o
  5. Saleem, M.; Kim, H. J.; Ali, M. S.; Lee, Y. S. Nat. Prod. Rep. 2005, 22, 696. https://doi.org/10.1039/b514045p
  6. Apers, S.; Vlietinck, A.; Pieters, L. Phytochem. Rev. 2004, 2, 201.
  7. Reynaud, J.; Guilet, D.; Terreux, R.; Lussignol, M.; Walchshofer, N. Nat. Prod. Rep. 2005, 22, 504. https://doi.org/10.1039/b416248j
  8. Maurya, R.; Yadav, P. P. Nat. Prod. Rep. 2005, 22, 400. https://doi.org/10.1039/b505071p
  9. Ohata, S.; Ishibashi, Y.; Shimada, T.; Takahashi, N.; Sugamori, T.; Sakane, T.; Hirano, Y.; Oyake, N.; Murakami, Y.; Higami, T. Clin. Exp. Pharmacol. Physiol. 2006, 33, 381. https://doi.org/10.1111/j.1440-1681.2006.04379.x
  10. Ohkawa, S.; Fukatsu, K.; Miki, S.; Hashimoto, T.; Sakamoto, J.; Doi, T.; Nagai, Y.; Aono, T. J. Med. Chem. 1997, 40, 559.
  11. Park, D. Y.; Gowrisankar, S.; Kim, J. N. Bull. Korean Chem. Soc. 2005, 26, 1440. https://doi.org/10.5012/bkcs.2005.26.9.1440
  12. Lin, H.; Schall, A.; Reiser, O. Synlett 2005, 2603.
  13. Kurono, N.; Honda, E.; Komatsu, F.; Orito, K.; Tokuda, M. Tetrahedron 2004, 60, 1791. https://doi.org/10.1016/j.tet.2003.12.038
  14. Vailard, S. E.; Postigo, A.; Rossi, R. A. J. Org. Chem. 2002, 67, 8500. https://doi.org/10.1021/jo026404m
  15. Terstiege, I.; Maleczka, R. E. J. Org. Chem. 1999, 64, 342. https://doi.org/10.1021/jo982332g
  16. Snider, B. B.; Han, L.; Xie, C. J. Org. Chem. 1997, 62, 6978. https://doi.org/10.1021/jo9708506
  17. Kokubo, K.; Harada, K.; Mochizuki, E.; Oshima, T. Tetrahedron Lett. 2010, 51, 955. https://doi.org/10.1016/j.tetlet.2009.12.047
  18. Engler, T. A.; Iyengar, R. J. Org. Chem. 1998, 63, 1929. https://doi.org/10.1021/jo971937u
  19. Rupprecht, K. M.; Boger, J.; Koogsteen, K.; Nachbar, R. B.; Springer, J. P. J. Org. Chem. 1991, 56, 6180. https://doi.org/10.1021/jo00021a042
  20. Barlugenga, J.; Fananas, F. J.; Sanz, R.; Marcis, C. Chem. -Eur. J. 2005, 11, 5397. https://doi.org/10.1002/chem.200500377
  21. Kneisel, F. F.; Monguchi, Y.; Knapp, K. M.; Zipse, H.; Knochel, P. Tetrahedron Lett. 2002, 43, 4875. https://doi.org/10.1016/S0040-4039(02)00839-0
  22. Plotkin, M.; Chen, S.; Spoors, P. G. Tetrahedron Lett. 2000, 41, 2269. https://doi.org/10.1016/S0040-4039(00)00159-3
  23. Nakao, J.; Inoue, R.; Shinokubo, H.; Oshima, K. J. Org. Chem. 1997, 62, 1910. https://doi.org/10.1021/jo970002a
  24. Rene, O.; Lapointe, D.; Fagnou, K. Org. Lett. 2009, 11, 4560. https://doi.org/10.1021/ol901799p
  25. Natori, Y.; Tsutsui, H.; Sato, N.; Nakamura, S.; Nambu, H.; Shiro, M.; Hsshimoto, S. J. Org. Chem. 2009, 74, 4418. https://doi.org/10.1021/jo900502d
  26. Grant, V. H.; Liu, B. Tetrahedron Lett. 2005, 46, 1237. https://doi.org/10.1016/j.tetlet.2005.01.006
  27. Zhang, H.; Ferreira, E. M.; Stoltz, B. M. Angew. Chem., Int. Ed. 2004, 43, 6144. https://doi.org/10.1002/anie.200461294
  28. Trost, B. M.; Thiel, O. R.; Tsui, H.-C. J. Am. Chem. Soc. 2003, 125, 13155. https://doi.org/10.1021/ja0364118
  29. Cheung, W.-H.; Zheng, S.-L.; Yu, W. Y.; Zhou, G.-C.; Che, C.-M. Org. Lett. 2003, 5, 2535. https://doi.org/10.1021/ol034806q
  30. Zheng, S. L.; Yu, W. Y.; Xu, M. X.; Che, C.-M. Tetrahedron Lett. 2003, 44, 1445. https://doi.org/10.1016/S0040-4039(02)02860-5
  31. Saito, H.; Oishi, H.; Kitagaki, S.; Nakamura, S.; Anada, M.; Hashimoto, S. Org. Lett. 2002, 4, 3887. https://doi.org/10.1021/ol0267127
  32. Kuwabe, S.-I.; Torraca, K. E.; Buchwald, S. L. J. Am. Chem. Soc. 2001, 123, 12202. https://doi.org/10.1021/ja012046d
  33. Choi, K.-S.; Kim, S.-G. Eur. J. Org. Chem. 2012, 1119.
  34. Lee, Y.; Seo, S. W.; Kim, S.-G. Adv. Synth. Catal. 2011, 353, 2671 https://doi.org/10.1002/adsc.201100324
  35. Gwon, S. H.; Kim, S.; Kim, S.-G. Bull. Korean Chem. Soc. 2011, 32, 4163. https://doi.org/10.5012/bkcs.2011.32.12.4163
  36. Lee, Y.; Kim, S.-G. Bull. Korean Chem. Soc. 2011, 32, 311. https://doi.org/10.5012/bkcs.2011.32.1.311
  37. Choi, K.-S.; Kim, S.-G. Tetrahedron Lett. 2010, 51, 5203. https://doi.org/10.1016/j.tetlet.2010.07.138
  38. Choi, K.-S.; Kim, S.-G. Synthesis 2010, 3999.
  39. Kim, S.-G. Bull. Korean Chem. Soc. 2009, 30, 2519. https://doi.org/10.5012/bkcs.2009.30.11.2519
  40. Kim, S.- G. Tetrahedron Lett. 2008, 49, 6148. https://doi.org/10.1016/j.tetlet.2008.08.025
  41. Rios, R.; Sunden, H.; Vesely, J.; Zhao, G.-L.; Dziedzic, P.; Córdova, A. Adv. Synth. Catal. 2007, 349, 1028. https://doi.org/10.1002/adsc.200700032
  42. Xie, H.; Zu, L.; Li, H.; Wang, J.; Wang, W. J. Am. Chem. Soc. 2007, 129, 10886. https://doi.org/10.1021/ja073262a
  43. Ibrahem, I.; Zhao, G.-L.; Rios, R.; Vesely, J.; Sunden, H.; Dziedzic, P.; Cordova, A. Chem Eur. J. 2007, 14, 7867.
  44. Li, Q-B.; Zhou, F.-T.; Liu, Z.-G.; Li, X.-F.; Zhu, W.-D.; Xie, J.-W. J. Org. Chem. 2011, 76, 7222. https://doi.org/10.1021/jo2008675
  45. Xu, L.-W.; Li, L.; Shi, Z.-H. Adv. Synth. Catal. 2010, 352, 243. https://doi.org/10.1002/adsc.200900797
  46. Bertelsen, S.; Jørgensen, K. A. Chem. Soc. Rev. 2009, 38, 2178. https://doi.org/10.1039/b903816g
  47. Melchiorre, P.; Marigo, M.; Carlone, A.; Bartoli, G. Angew. Chem. Int. Ed. 2008, 47, 6138. https://doi.org/10.1002/anie.200705523
  48. Mielgo, A.; Palomo, C. Chem. Asian. J. 2008, 3, 922. https://doi.org/10.1002/asia.200700417
  49. Palomo, C.; Mielgo, A. Angew. Chem. Int. Ed. 2006, 45, 7876. https://doi.org/10.1002/anie.200602943

Cited by

  1. ]furans and 2,3-Dihydrobenzofurans vol.78, pp.11, 2013, https://doi.org/10.1021/jo400621r
  2. Recent Applications of Potassium Carbonate in Organic Synthesis vol.46, pp.5, 2014, https://doi.org/10.1080/00304948.2014.944402
  3. -Promoted Cascade Michael/Aza-Cyclization Reactions vol.36, pp.1, 2015, https://doi.org/10.1002/bkcs.10049
  4. X & Y Chromosomal Variations: Hormones, Brain Development, and Neurodevelopmental Performance vol.5, pp.2, 2016, https://doi.org/10.4199/C00134ED1V01Y201506DBR013
  5. Stereodivergent Organocatalytic Intramolecular Michael Addition/Lactonization for the Asymmetric Synthesis of Substituted Dihydrobenzofurans and Tetrahydrofurans vol.20, pp.31, 2014, https://doi.org/10.1002/chem.201402684
  6. Asymmetric Construction of Benzindoloquinolizidine: Application of An Organocatalytic Enantioselective Conjugate Addition-Cyclization Cascade Reaction vol.35, pp.2, 2012, https://doi.org/10.5012/bkcs.2014.35.2.625
  7. Quantum Reality in the Selective Reduction of a Benzofuran System vol.24, pp.11, 2012, https://doi.org/10.3390/molecules24112061
  8. Palladium-catalyzed diastereoselective synthesis of 2,2,3-trisubstituted dihydrobenzofurans via intramolecular trapping of O-ylides with activated alkenes vol.396, pp.None, 2012, https://doi.org/10.1016/j.jcat.2021.02.032