Bulletin of the Korean Chemical Society

Korean Chemical Society (대한화학회)
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Synthesis of 3-Benzylcoumarins Using Suzuki Coupling Reaction

  • Kwon, Young-Bum (Department of Advanced Material Chemistry, Korea University) ;
  • Park, Jin-Hyung (Department of Advanced Material Chemistry, Korea University) ;
  • Choi, Bo-Ram (Department of Advanced Material Chemistry, Korea University) ;
  • Kim, Hyun-Soo (Department of Advanced Material Chemistry, Korea University) ;
  • Yoon, Cheol-Min (Department of Advanced Material Chemistry, Korea University)
  • Received : 2011.03.05
  • Accepted : 2011.06.28
  • Published : 2011.08.20
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Abstract

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References

  1. Hepworth, J. D.; Gabbutt, C. D.; Heron, B.M. In Comprehensive Heterocyclic Chemistry-II; Katritzky, A. R., Rees, C. W., Scriven, E. F. V., Eds.; Pergamon: New York, 1996; Vol. 5, pp 417-434.
  2. Neyts, J.; Clercq, E. D.; Singha, R.; Chang, Y. H.; Das, A. R.; Chakraborty, S. K.; Hong, S. C.; Tsay, S. C.; Hsu, M. H.; Hwu, J. R. J. Med. Chem. 2009, 52, 1486. https://doi.org/10.1021/jm801240d
  3. O'Kennedy, R., Thornes, R. D., Eds.; In Coumarins: Biology, Applications and Mode of Action; Wiley: Chichester, U.K. 1997.
  4. Brun, M. P.; Bischoff, L.; Garbay, C. Angew. Chem., Int. Ed. 2004, 43, 3432. https://doi.org/10.1002/anie.200454116
  5. Lee, J. H.; Jeong, A. R.; Shin, I-.S.; Kim, H- .J.; Hong, J.-I. Organic Lett. 2010, 12, 764. https://doi.org/10.1021/ol902852g
  6. Jung, M. E.; Allen, D. A. Organic Lett. 2009, 11, 757. https://doi.org/10.1021/ol802792g
  7. Chen, G.; Tokunaga, N.; Hayashi, T. Organic Lett. 2005, 7, 2285. https://doi.org/10.1021/ol0507367
  8. Stoffman, E. J. L.; Clive, D. L. K. Org. Biomol. Chem. 2009, 7, 4862. https://doi.org/10.1039/b914580j
  9. von Pechmann, H. Chem. Ber. 1883, 16, 2119. https://doi.org/10.1002/cber.188301602117
  10. Rabjohn, N. Org. React. 1976, 24, 261.
  11. Sugino, T.; Tanaka, K. Chemistry Lett. 2001, 513.
  12. Jones, G. Org. React. 1967, 15, 204.
  13. Brufola, G.; Fringuelli, F.; Piermatti, O.; Pizzo, F. Heterocycle 1996, 43, 1257. https://doi.org/10.3987/COM-96-7447
  14. Perkin, W. H. J. Chem. Soc. 1875, 28, 11.
  15. Johnson, J. R. Org. React. 1942, 1, 210.
  16. Shriner, R. L. Org. React. 1942, 1, 1.
  17. Narasimhan, N. S.; Mali, R. S.; Barve, M. V. Synthesis 1979, 906.
  18. Yavari, I.; Hekmat-Shoar, R.; Zonouzi, A. Tetrahedron Lett. 1998, 39, 2391. https://doi.org/10.1016/S0040-4039(98)00206-8
  19. Ramesh, E.; Raghunathan, R. Tetrahedron Lett. 2008, 49, 1812. https://doi.org/10.1016/j.tetlet.2008.01.059
  20. Upadhyay, P. K.; Kumar, P. Tetrahedron Lett. 2009, 50, 236. https://doi.org/10.1016/j.tetlet.2008.10.133
  21. Wang, W.; Ding, Q.; Fana, R.; Wua, J.Tetrahedron Lett. 2007, 48, 3647. https://doi.org/10.1016/j.tetlet.2007.03.142
  22. Das, A. R.; Medda, A.; Singha, R. Tetrahedron Lett. 2010, 51, 1099. https://doi.org/10.1016/j.tetlet.2009.12.089
  23. Wu, J.; Wang, L.; Fathi, R.; Yang, Z. Tetrahedron Lett. 2002, 43, 4395. https://doi.org/10.1016/S0040-4039(02)00718-9
  24. Wu, J.; Zhanga, L.; Xiaa, H.-G. Tetrahedron Lett. 2006, 47, 1525. https://doi.org/10.1016/j.tetlet.2006.01.020
  25. Zhang, L.; Meng, T.; Fan, R.; Wu, J. J. Org. Chem. 2007, 72, 7279. https://doi.org/10.1021/jo071117+
  26. Torang, J.; Vanderheiden, S.; Nieger, M.; Brase, S. Eur. J. Org. Chem. 2007, 943
  27. Britto, N.; Gore, V. G.; Mali, R. S.; Ranade, A. C. Synth. Commun. 1989, 19, 1899. https://doi.org/10.1080/00397918908052581
  28. Jana, R.; Trivedi, R.; Tunge, J. A. Organic Lett. 2009, 11, 3434. https://doi.org/10.1021/ol901288r
  29. Johnson, J. A. Pharmacotherapy 2008, 28, 1081. https://doi.org/10.1592/phco.28.9.1081
  30. Nichele, T. Z.; Monteiro, A. L. Tetrahedron Lett. 2007, 48, 7472. https://doi.org/10.1016/j.tetlet.2007.08.072
  31. Kuwano, R.; Yokogi, M. Chem. Commun. 2005, 5899.
  32. Roberts, J. S.; Klabunde, K. J. J. Am. Chem. Soc. 1977, 99, 2509. https://doi.org/10.1021/ja00450a018
  33. Kuwano, R.; Kondo, Y.; Matsuyama, Y. J. Am. Chem. Soc. 2003, 125, 12104. https://doi.org/10.1021/ja037735z
  34. Kaye, P. T.; Musa, M. A.; Nocanda, X. W. Synthesis 2003, 531.
  35. Kaye, P. T.; Musa, M. A. Synth. Commun. 2004, 34, 3409. https://doi.org/10.1081/SCC-200030643

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