Bulletin of the Korean Chemical Society

Korean Chemical Society (대한화학회)
권호 표지
DOI QR코드

DOI QR Code

Isomerization of 1,3-Diarylprop-2-yn-1-ols to Chalcones in the Presence of Potassium Hydroxide

  • Cho, Chan-Sik (Research Institute of Industrial Technology, Kyungpook National University) ;
  • Seok, Hyo-Jin (Department of Applied Chemistry, College of Engineering, Kyungpook National University) ;
  • Shim, Sang-Chul (Department of Applied Chemistry, College of Engineering, Kyungpook National University)
  • Published : 2005.07.20
Download PDF
⟨ Previous Next ⟩

Abstract

Keywords

References

  1. Lu, X.; Ji, J.; Guo, C.; Shen, W. J. Organomet. Chem. 1992, 428, 259 https://doi.org/10.1016/0022-328X(92)83235-A
  2. Shvo, Y.; Blum, Y.; Reshef, D. J. Organomet. Chem. 1982, 238, C79 https://doi.org/10.1016/S0022-328X(00)83809-7
  3. Tsuji, Y.; Yokoyama, Y.; Huh, K.-T.; Watanabe, Y. Bull. Chem. Soc. Jpn. 1987, 60, 3456 https://doi.org/10.1246/bcsj.60.3456
  4. Ma, D.; Lu, X. J. Chem. Soc., Chem. Commun. 1989, 890
  5. Trost, B. M.; Livingston, R. C. J. Am. Chem. Soc. 1995, 117, 9586 https://doi.org/10.1021/ja00142a036
  6. Saiah, M. K. E.; Pellicciari, R. Tetrahedron Lett. 1995, 36, 4497 https://doi.org/10.1016/0040-4039(95)00768-8
  7. Ma, D.; Lu, X. Tetrahedron Lett. 1989, 30, 2109 https://doi.org/10.1016/S0040-4039(01)93725-6
  8. Arcadi, A.; Cacchi, S.; Marinelli, F.; Misiti, D. Tetrahedron Lett. 1988, 29, 1457 https://doi.org/10.1016/S0040-4039(00)80324-X
  9. Ishikawa, T.; Mizuta, T.; Hagiwara, K.; Aikawa, T.; Kudo, T.; Saito, S. J. Org. Chem. 2003, 68, 3702 https://doi.org/10.1021/jo026592g
  10. Minn, K. Synlett 1991, 115
  11. Kundu, N. G.; Das, P. J. Chem. Soc., Chem. Commun. 1995, 99
  12. Muller, T. J. J.; Ansorge, M.; Aktah, D. Angew. Chem. Int. Ed. 2000, 39, 1253 https://doi.org/10.1002/(SICI)1521-3773(20000403)39:7<1253::AID-ANIE1253>3.0.CO;2-X
  13. Cho, C. S.; Oh, B. H.; Shim, S. C. Tetrahedron Lett. 1999, 40, 1499 https://doi.org/10.1016/S0040-4039(98)02661-6
  14. Cho, C. S.; Oh, B. H.; Shim, S. C. J. Heterocyclic Chem. 1999, 36, 1175 https://doi.org/10.1002/jhet.5570360510
  15. Cho, C. S.; Kim, J. S.; Oh, B. H.; Kim, T.-J.; Shim, S. C. Tetrahedron 2000, 56, 7747 https://doi.org/10.1016/S0040-4020(00)00694-3
  16. Cho, C. S.; Oh, B. H.; Kim, J. S.; Kim, T.-J.; Shim, S. C. Chem. Commun. 2000, 1885
  17. Cho, C. S.; Kim, B. T.; Kim, T.-J.; Shim, S. C. Chem. Commun. 2001, 2576
  18. Cho, C. S.; Kim, T. K.; Kim, B. T.; Kim, T.-J.; Shim, S. C. J. Organomet. Chem. 2002, 650, 65 https://doi.org/10.1016/S0022-328X(02)01170-1
  19. Cho, C. S.; Kim, B. T.; Choi, H.-J.; Kim, T.-J.; Shim, S. C. Tetrahedron 2003, 59, 7997 https://doi.org/10.1016/j.tet.2003.08.027
  20. Cho, C. S.; Lee, N. Y.; Kim, T.-J.; Shim, S. C. J. Heterocyclic Chem. 2004, 41, 423 https://doi.org/10.1002/jhet.5570410320
  21. Cho, C. S.; Lee, N. Y.; Kim, T.-J.; Shim, S. C. J. Heterocyclic Chem. 2004, 41, 409 https://doi.org/10.1002/jhet.5570410317
  22. Bagley, M. C.; Bashford, K. E.; Hesketh, C. L.; Moody, C. J. J. Am. Chem. Soc. 2000, 122, 3301 https://doi.org/10.1021/ja994247b
  23. Sonogashira, K. J. Organomet. Chem. 2002, 653, 46 https://doi.org/10.1016/S0022-328X(02)01158-0
  24. Yasuhara, A.; Suzuki, N.; Yoshino, T.; Takeda, Y.; Sakamoto, T. Tetrahedron Lett. 2002, 43, 6579 https://doi.org/10.1016/S0040-4039(02)01439-9
  25. Arai, S.; Tsuge, H.; Oku, M.; Miura, M.; Shioiri, T. Tetrahedron 2002, 58, 1623 https://doi.org/10.1016/S0040-4020(02)00028-5
  26. Chen, W.; Egar, A. L.; Hursthouse, M. B.; Malik, K. M. A.; Mathews, J. E.; Roberts, S. M. Tetrahedron Lett. 1998, 39, 8495 https://doi.org/10.1016/S0040-4039(98)01249-0
  27. Kumaraswamy, G.; Sastry, M. N. V.; Jena, N.; Kumar, K. R.; Vairamani, M. Tetrahedron: Asymmetry 2003, 14, 3797 https://doi.org/10.1016/j.tetasy.2003.08.022
  28. Timmons, C.; Chen, D.; Barney, C. E.; Kirtane, S.; Li, G. Tetrahedron 2004, 60, 12095
  29. Bharadwaj, A. R.; Scheidt, K. A. Org. Lett. 2004, 6, 2465 https://doi.org/10.1021/ol049044t
  30. Chan, P. W. H.; Kamijo, S.; Yamamoto, Y. Synlett 2001, 910
  31. Synlett Chan, P.W.H.;Kamijo, S.;Yamamoto, Y.

Cited by

  1. Base-Catalyzed Cascade 1,3-H Shift/Cyclization Reaction to Construct Polyaromatic Furans vol.353, pp.5, 2011, https://doi.org/10.1002/adsc.201000833
  2. Isomerization of 1,3-Diarylprop-2-yn-1-ols to Chalcones in the Presence of Potassium Hydroxide. vol.36, pp.49, 2005, https://doi.org/10.1002/chin.200549099
  3. Potassium Hydroxide-Mediated Cascade Isomerization and Oxy-Michael Addition of 3-(2-Hydroxymethylphenyl)-1-arylprop-2-yn-1-ols Leading to Isobenzofurans vol.27, pp.5, 2005, https://doi.org/10.5012/bkcs.2006.27.5.776
  4. Stereoselective synthesis of enynones via base-catalyzed isomerization of 1,5-disubstituted-2,4-pentadiynyl silyl ethers or their alcohol derivatives vol.8, pp.21, 2010, https://doi.org/10.1039/c0ob00344a
  5. One‐Pot Alkynylation of Azaaryl Aldehydes and Spontaneous Base‐Free Rearrangement into Enone Esters: an Autoinductive Mechanism vol.2018, pp.12, 2005, https://doi.org/10.1002/ejoc.201701566