Bulletin of the Korean Chemical Society

Korean Chemical Society (대한화학회)
권호 표지
DOI QR코드

DOI QR Code

Potassium Hydroxide-Mediated Cascade Isomerization and Oxy-Michael Addition of 3-(2-Hydroxymethylphenyl)-1-arylprop-2-yn-1-ols Leading to Isobenzofurans

  • Cho, Chan-Sik (Research Institute of Industrial Technology, Kyungpook National University) ;
  • Shim, Sang-Chul (Department of Applied Chemistry, College of Engineering, Kyungpook National University)
  • Published : 2006.05.20
Download PDF
⟨ Previous Next ⟩

Abstract

Keywords

References

  1. Padwa, A.; Krumpe, K. E.; Weingarten, M. D. J. Org. Chem.1995, 60, 5595 https://doi.org/10.1021/jo00122a047
  2. Hiroya, K.; Jouka, R.; Kameda, M.; Yasuhara, A.; Sakamoto, T.Tetrahedron 2001, 57, 9697 https://doi.org/10.1016/S0040-4020(01)00991-7
  3. Gabriele, B.; Salerno, G.; Fazio, A.; Pittelli, R. Tetrahedron 2003,59, 6251 https://doi.org/10.1016/S0040-4020(03)01019-6
  4. Mukhopadhyay, R.; Kundu, N. G. Tetrahedron 2001,57, 9475 https://doi.org/10.1016/S0040-4020(01)00943-7
  5. Suwa, T.; Nishino, K.; Miyatake, M.; Shibata, I.; Baba, A.Tetrahedron Lett. 2000, 41, 3403 https://doi.org/10.1016/S0040-4039(00)00388-9
  6. 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
  7. Cho, C. S. J. Organomet.Chem. 2005, 690, 4094 https://doi.org/10.1016/j.jorganchem.2005.06.002
  8. 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
  9. Sonogashira, K. J. Organomet. Chem. 2002, 653, 46 andreferences cited therein https://doi.org/10.1016/S0022-328X(02)01158-0
  10. Lu, X.; Ji, J.; Guo, C.; Shen, W. J. Organomet. Chem. 1992,428, 259 https://doi.org/10.1016/0022-328X(92)83235-A
  11. Shvo, Y.; Blum, Y.; Reshef, D. J. Organomet. Chem.1982, 238, C79 https://doi.org/10.1016/S0022-328X(00)86839-4
  12. Tsuji, Y.; Yokoyama, Y.; Huh, K.-T.;Watanabe, Y. Bull. Chem. Soc. Jpn. 1987, 60, 3456 https://doi.org/10.1246/bcsj.60.3456
  13. Ma, D.;Lu, X. J. Chem. Soc., Chem. Commun. 1989, 890
  14. Trost, B.M.; Livingston, R. C. J. Am. Chem. Soc. 1995, 117, 9586 https://doi.org/10.1021/ja00142a036
  15. Saiah, M. K. E.; Pellicciari, R. Tetrahedron Lett. 1995, 36, 4497 https://doi.org/10.1016/0040-4039(95)00768-8
  16. Ma, D.; Lu, X. Tetrahedron Lett. 1989, 30, 2109 https://doi.org/10.1016/S0040-4039(01)93725-6
  17. Arcadi, A.; Cacchi, S.; Marinelli, F.; Misti, D. TetrahedronLett. 1988, 29, 1457 https://doi.org/10.1016/S0040-4039(00)80324-X
  18. Ishikawa, T.; Mizuta, T.; Hagiwara, K.;Aikawa, T.; Kudo, T.; Saito, S. J. Org. Chem. 2003, 68, 3702 https://doi.org/10.1021/jo026592g
  19. We already reported on the isomerization of 1,3-diarylprop-2-yn-1-ols to chalcones in the presence of KOH: Cho, C. S.; Seok, H.J.; Shim, S. C. Bull. Korean Chem. Soc. 2005, 26, 1107 https://doi.org/10.5012/bkcs.2005.26.7.1107
  20. Minn, K. Synlett 1991, 115
  21. Kundu, N. G.; Das, P. J. Chem.Soc., Chem. Commun. 1995, 99
  22. 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

Cited by

  1. Potassium Hydroxide-Mediated Cascade Isomerization and Oxy-Michael Addition of 3-(2-Hydroxymethylphenyl)-1-arylprop-2-yn-1-ols Leading to Isobenzofurans. vol.37, pp.51, 2006, https://doi.org/10.1002/chin.200651081
  2. 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