Bulletin of the Korean Chemical Society

Korean Chemical Society (대한화학회)
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Rapid and Effective Multihalogenations of 2,2',5',2''-Terthiophene with 2-Halo-4,5-dichloropyridazin-3(2H)-ones under Ambient Conditions

  • Kim, Eun-Jung (Department of Chemistry & Environmental Biotechnology National Core Research Center, Research Institute of Natural Sciences, Graduate School for Molecular Materials and Nanochemistry, Gyeongsang National University) ;
  • Jung, Kwang-Ju (Department of Chemistry & Environmental Biotechnology National Core Research Center, Research Institute of Natural Sciences, Graduate School for Molecular Materials and Nanochemistry, Gyeongsang National University) ;
  • Lee, In-Hye (Department of Chemistry & Environmental Biotechnology National Core Research Center, Research Institute of Natural Sciences, Graduate School for Molecular Materials and Nanochemistry, Gyeongsang National University) ;
  • Kim, Bo-Ram (Department of Chemistry & Environmental Biotechnology National Core Research Center, Research Institute of Natural Sciences, Graduate School for Molecular Materials and Nanochemistry, Gyeongsang National University) ;
  • Kim, Jeum-Jong (Advanced Solar Technology Research Department, Electronic and Telecommunications Research Institute) ;
  • Park, Jong-Keun (Department of Chemistry Education, Gyeongsang National University) ;
  • Lee, Sang-Gyeong (Department of Chemistry & Environmental Biotechnology National Core Research Center, Research Institute of Natural Sciences, Graduate School for Molecular Materials and Nanochemistry, Gyeongsang National University) ;
  • Yoon, Yong-Jin (Department of Chemistry & Environmental Biotechnology National Core Research Center, Research Institute of Natural Sciences, Graduate School for Molecular Materials and Nanochemistry, Gyeongsang National University)
  • Received : 2010.07.01
  • Accepted : 2010.08.06
  • Published : 2010.10.20
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References

  1. Kim, B. R.; Lee, H. G.; Kim, E. J.; Lee, S. G.; Yoon, Y. J. J. Org. Chem. 2010, 75, 484. https://doi.org/10.1021/jo902356e
  2. Lee, H. G.; Kim, M. J.; Lee, I. H.; Kim, E. J.; Kim, B. R.; Yoon, Y. J. Bull. Korean Chem. Soc. 2010, 31, 1061. https://doi.org/10.5012/bkcs.2010.31.04.1061
  3. Jung, K. J.; Kang, S. B.; Won, J. E.; Park, S. E.; Park, K. H.; Park, J. K.; Lee, S. G.; Yoon, Y. J. Synlett. 2009, 490.
  4. Kim, M. J.; Kim, J. J.; Won, J. E.; Kang, S. B.; Park, S. E.; Jung, K. J.; Lee, S. G.; Yoon, Y. J. Bull. Korean Chem. Soc. 2008, 29, 2247. https://doi.org/10.5012/bkcs.2008.29.11.2247
  5. Kang, S. B.; Yim, H. S.;Won, J. E.; Kim, M. J.; Kim, J. J.; Kim, H. K.; Lee, S. G.; Yoon, Y. J. Bull. Korean Chem. Soc. 2008, 29, 1025. https://doi.org/10.5012/bkcs.2008.29.5.1025
  6. Won, J. E.; Kim, H. K.; Kim, J. J.; Yim, H. S.; Kim, M. J.; Kang, S. B.; Chung, H. A.; Lee, S. G.; Yoon, Y. J. Tetrahedron 2007, 63, 12720. https://doi.org/10.1016/j.tet.2007.10.011
  7. Park, Y. D.; Kim, H. K.; Kim, J. J.; Cho, S. D.; Kim, S. K.; Shiro, M.; Yoon, Y. J. J. Org. Chem. 2003, 68, 9113. https://doi.org/10.1021/jo0301503
  8. Park, Y. D.; Kim, J. J.; Cho, S. D.; Lee, S. G.; Falck, J. R.; Yoon, Y. J. Synthesis 2005, 1136.
  9. Kim, J. J.; Kweon, D. H.; Cho, S. D.; Kim, H. K.; Jung, E. Y.; Lee, S. G.; Falck, J. R.; Yoon, Y. J. Tetrahedron 2005, 61, 5889. https://doi.org/10.1016/j.tet.2005.03.138
  10. Kim, S. K.; Kweon, D. H.; Cho, S. D.; Kang, Y. J.; Park, K. H.; Lee, S. G.; Yoon, Y. J. J. Heterocycl. Chem. 2005, 42, 353. https://doi.org/10.1002/jhet.5570420302
  11. Kim, J. J.; Park, Y. D.; Kim, H. K.; Cho, S. D.; Kim, J. K.; Lee, S. G.; Yoon, Y. J. Synth. Commun. 2005, 35, 731. https://doi.org/10.1081/SCC-200050375
  12. Park, Y. D.; Kim, J. J.; Kim, H. K.; Cho, S. D.; Kang, Y. J.; Park, K. H.; Lee, S. G.; Yoon, Y. J. Synth. Commun. 2005, 35, 371. https://doi.org/10.1081/SCC-200048939
  13. Lee, S. G.; Kim, J. J.; Kim, H. K.; Kweon, D. H.; Kang, Y. J.; Cho, S. D.; Kim, S. K.; Yoon, Y. J. Curr. Org. Chem. 2004, 8, 1463. https://doi.org/10.2174/1385272043369818
  14. Kim, S. K.; Cho, S. D.; Kweon, D. H.; Yoon, Y. J.; Kim, J. H.; Heo, J. N. J. Heterocycl. Chem. 1997, 34, 209. https://doi.org/10.1002/jhet.5570340131
  15. Beaupre, S.; Breton, S., A.-C.; Dumas, J.; Leclerc, M. Chem. Mater. 2009, 21, 1504. https://doi.org/10.1021/cm802941e
  16. Tian, H.; Shi, J.; He, B.; Hu, N. H.; Dong, S. Q.; Yan, D. H.; Zhang, J. P.; Geng, Y. H.; Wang, F. S. Adv. Funct. Mater. 2007, 17, 1940. https://doi.org/10.1002/adfm.200706198
  17. Gondo, S.; Goto, Y.; Era, M. Mol. Cryst. Liq. Cryst. 2007, 470, 353. https://doi.org/10.1080/15421400701503600
  18. Ellinger, S.; Kreyers, A.; Ziener, U.; Hoffmann- Richter, C.; Landfester, K.; Moller, M. Eur. J. Org. Chem. 2007, 25, 5686.
  19. Collins, G. E.; Burrell, A. K.; Blandford, E. J.; Officer, D. L. Tetrahedron 2007, 63, 11141. https://doi.org/10.1016/j.tet.2007.08.022
  20. Facchetti, A.; Yoon, M.-H.; Stern, C. L.; Hutchison, G. R.; Ratner, M. A.; Marks, T. J. J. Am. Chem. Soc. 2004, 126, 13480. https://doi.org/10.1021/ja048988a
  21. Chisaka, J.; Lu, M.; Nagamatsu, S.; Chikamatsu, M.; Yoshida, Y.; Goto, M.; Azumi, R.; Yamashita, M.; Yase, K. Chem. Mater. 2007, 19, 2694. https://doi.org/10.1021/cm0701658
  22. Zrig, S.; Koeckelberghs, G.; Verbiest, T.; Andrioletti, B.; Rose, E.; Persoons, A.; Asselberghs, I.; Clays, K. J. Org. Chem. 2007, 72, 5855. https://doi.org/10.1021/jo070888a
  23. Cremer, J.; Briehn, C. A. Chem. Mater. 2007, 19, 4155. https://doi.org/10.1021/cm0700448
  24. Pappenfus, T. M.; Melby, J. H.; Hansen, B. B.; Sumption, D. M.; Hubers, S. A.; Hanzen, D. E.; Ewbank, P. C.; McGee, K. A.; Burand, M. W.; Mann, K. R. Org. Lett. 2007, 9, 3721. https://doi.org/10.1021/ol071369x
  25. Melucci, M.; Frere, P.; Allain, M.; Levillain, E.; Barbarella, G.; Roncali, J. Tetrahedron 2007, 63, 9774. https://doi.org/10.1016/j.tet.2007.07.006
  26. Yui, K.; Aso, Y.; Otsubo, T.; Ogura, F. Bull. Chem. Soc. Jpn. 1989, 62, 1539. https://doi.org/10.1246/bcsj.62.1539
  27. Kim, J. J.; Kweon, D. H.; Cho, S. D.; Kim, H. K.; Lee, S. G.; Yoon, Y. J. Synlett 2006, 194.
  28. Kim, J. J.; Kweon, D. H.; Cho, S. D.; Kim, H. K.; Jung, E. Y.; Lee, S. G.; Falck, J. R.; Yoon, Y. J. Tetrahedron 2005, 61, 5889. https://doi.org/10.1016/j.tet.2005.03.138
  29. Joule, J. A.; Mills, K.; Smith, G. F. Heterocyclic Chemistry, 3rd ed.; Chapman & Hall: London, 1996; p 225.
  30. Iu, Y.; Ye, M.; Guo, H.-Z.; Zhao, Y.-Y.; Guo, D.-A. J. Asian. Nat. Prod. Res. 2002, 4(3), 175. https://doi.org/10.1080/1028602021000000071
  31. Didier, D.; Sergeyev, S.; Geerts, Y. H. Tetrahedron 2007, 63(4), 941. https://doi.org/10.1016/j.tet.2006.11.029
  32. Nakayama, J.; Konishi, T.; Murabayashi, S.; Hoshino, M. Heterocycles 1987, 26(7), 1793. https://doi.org/10.3987/R-1987-07-1793
  33. Eachern, A. M.; Soucy, C.; Leitch, L. C.; Arnason, J. T.; Morand, P. Tetrahedron 1988, 44(9), 2403. https://doi.org/10.1016/S0040-4020(01)81692-6
  34. Facchetti, A.; Yoon, M.-H.; Stern, C. L.; Hutchison, G. R.; Ratner, M. A.; Marks, T. J. J. Am. Chem. Soc. 2004, 126(41), 13480. https://doi.org/10.1021/ja048988a

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