DOI QR코드

DOI QR Code

Lactonization of ω-Hydroxycarboxylic Acids Using (4,5-Dichloro-6-oxo-6H-pyridazin-1-yl)phosphoric Acid Diethyl Ester

  • Kim, Min-Jung (Department of Chemistry & Environmental Biotechnology National Core Research Center, Research Institute of Natural Science, Graduate School for Molecular Materials and Nanochemistry, Gyeongsang National University) ;
  • Kim, Jeum-Jong (Department of Chemistry & Environmental Biotechnology National Core Research Center, Research Institute of Natural Science, Graduate School for Molecular Materials and Nanochemistry, Gyeongsang National University) ;
  • Won, Ju-Eun (Department of Chemistry & Environmental Biotechnology National Core Research Center, Research Institute of Natural Science, Graduate School for Molecular Materials and Nanochemistry, Gyeongsang National University, Jinju 660-701, Korea) ;
  • Kang, Seung-Beom (Department of Chemistry & Environmental Biotechnology National Core Research Center, Research Institute of Natural Science, Graduate School for Molecular Materials and Nanochemistry, Gyeongsang National University) ;
  • Park, Song-Eun (Department of Chemistry & Environmental Biotechnology National Core Research Center, Research Institute of Natural Science, 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 Science, Graduate School for Molecular Materials and Nanochemistry, Gyeongsang National University) ;
  • Lee, Sang-Gyeong (Department of Chemistry & Environmental Biotechnology National Core Research Center, Research Institute of Natural Science, Graduate School for Molecular Materials and Nanochemistry, Gyeongsang National University, Jinju 660-701, Korea) ;
  • Yoon, Yong-Jin (Department of Chemistry & Environmental Biotechnology National Core Research Center, Research Institute of Natural Science, Graduate School for Molecular Materials and Nanochemistry, Gyeongsang National University)
  • Published : 2008.11.20

Abstract

Keywords

References

  1. Parenty, A.; Moreau, X.; Campagne, J.-M. Chem. Rev. 2006, 106, 911 https://doi.org/10.1021/cr0301402
  2. Andrus, M. B.; Argade, A. B. Tetrahedron Lett. 1996, 37, 5049 https://doi.org/10.1016/0040-4039(96)01014-3
  3. Boden, E. P.; Keck, G. E. J. Org. Chem. 1985, 50, 2394 https://doi.org/10.1021/jo00213a044
  4. Guillern, D.; Linstrumelle, G. Tetrahedron Lett. 1985, 26, 3811 https://doi.org/10.1016/S0040-4039(00)89257-6
  5. Mulzer, J.; Kirstein, H. M.; Buschmann, J.; Lehmann, C; Luger, P. J. Am. Chem. Soc. 1991, 113, 910 https://doi.org/10.1021/ja00003a026
  6. White, J. D.; Blakemore, P. R.; Browder, C. C.; Hong, J.; Lincoln, C. M.; Nagornyy, P. A.; Robarge, L. A.; Wardrop, D. J. J. Am. Chem. Soc. 2001, 123, 8593 https://doi.org/10.1021/ja011256n
  7. Inanaga, J.; Hirata, K.; Saeki, H.; Katsuki, T.; Yamaguchi, M. Bull. Chem. Soc. Jpn. 1979, 52, 1989 https://doi.org/10.1246/bcsj.52.1989
  8. Corey, E. J.; Nicolaou, K. C. J. Am. Chem. Soc. 1974, 96, 5614 https://doi.org/10.1021/ja00824a073
  9. Mukaiyama, T.; Usui, M.; Saigo, K. Chem. Lett. 1976, 49
  10. Venkatarman, K.; Wagle, D. R. Tetrahedron Lett. 1980, 21, 1983 https://doi.org/10.1016/S0040-4039(00)93663-3
  11. Shiina, I.; Kubota, M.; Ibuka, R. Tetrahedron Lett. 2002, 43, 7535 https://doi.org/10.1016/S0040-4039(02)01819-1
  12. Shiina, I.; Kubota, M.; Oshiumi, H.; Hashizume, M. J. Org. Chem. 2004, 69, 1822 https://doi.org/10.1021/jo030367x
  13. Shiina, I.; Kubota, T. Chem. Lett. 1994, 677
  14. Shiina, I. Tetrahedron 2004, 60, 1587 https://doi.org/10.1016/j.tet.2003.12.013
  15. Ishihara, K.; Kubota, M.; Kurihara, H.; Yamamoto, H. J. Org. Chem. 1996, 61, 4560 https://doi.org/10.1021/jo952237x
  16. Oohashi, Y.; Fukumoto, K.; Mukaiyama, T. Chem. Lett. 2005, 34, 72 https://doi.org/10.1246/cl.2005.72
  17. Fusisawa, T.; Mori, T.; Fukumoto, K.; Sato, T. Chem. Lett. 1982, 1891
  18. Isobe, T.; Ishikawa, T. J. Org. Chem. 1999, 64, 6984 https://doi.org/10.1021/jo990210y
  19. Ahmed, A.; Taniguchi, N.; Kinoshita, H.; Inomata, K.; Kotake, H. Bull. Chem. Soc. Jpn. 1984, 57, 781 https://doi.org/10.1246/bcsj.57.781
  20. Kaiho, T.; Masamune, S.; Toyoda, T. J. Org. Chem. 1982, 47, 1612 https://doi.org/10.1021/jo00347a061
  21. Corey, E. T.; Hua, D. H.; Pan, B. C.; Seitz, S. P. J. Am. Chem. Soc. 1982, 104, 6818 https://doi.org/10.1021/ja00388a074
  22. Diago-Meseguer, J.; PAlomo- Coll, A. L.; Fernandez-Lizarbe, J. R.; Zugaza-Bilbao, A. Synthesis 1980, 547
  23. Coste, J.; Frerot, E.; Jouin, P.; Castro, B. Tetrahedron Lett. 1991, 32, 1967 https://doi.org/10.1016/0040-4039(91)85015-W
  24. Frerot, E.; Coste, J.; Pantaloni, A.; Dufour, P. Tetrahedron 1991, 47, 259 https://doi.org/10.1016/S0040-4020(01)80922-4
  25. Han, S. Y.; Kim, Y. A. Tetrahedron 2004, 60, 2447 https://doi.org/10.1016/j.tet.2004.01.020
  26. Corey, E. J.; Brunelle, D. J. Tetrahedron Lett. 1976, 28, 3409
  27. Steliou, K.; Nowsielska, A. S.; Favre, A.; Poupart, M. A.; Hanessian, S. J. Am. Chem. Soc. 1980, 102, 7578 https://doi.org/10.1021/ja00545a038
  28. Steliou, K.; Poupart, M. A. J. Am. Chem. Soc. 1983, 105, 7130 https://doi.org/10.1021/ja00362a018
  29. Otera, J.; Yano, T.; Himeno, Y.; Nozaki, H. Tetrahedron Lett. 1986, 27, 4501 https://doi.org/10.1016/S0040-4039(00)84989-8
  30. Shiina, I.; Fukuda, Y.; Ishii, T.; Fujisawa, H.; Mukaiyama, T. Chem. Lett. 1998, 831
  31. Shiina, I.; Fujisawa, H.; Ishii, T.; Fukada, Y. Heterocycles 2000, 52, 1105 https://doi.org/10.3987/COM-99-S85
  32. Kim, J. J.; Kweon, D. H.; Cho, S. D.; Kim, H. K.; Lee, S. G.; Yoon, Y. J. Synlett 2006, 194
  33. Kim, J. J.; Kweon, D. H.; Cho, S. D.; Kim, H. K.; Lee, S. G.; Falck, J. R.; Yoon, Y. J. Tetrahedron 2005, 61, 5889 https://doi.org/10.1016/j.tet.2005.03.138
  34. Park, Y. D.; Kim, J. J.; Cho, S. D.; Lee, S. G.; Falck, J. R.; Yoon, Y. J. Synthesis 2005, 1136
  35. 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
  36. 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
  37. Kim, J. J.; Park, Y. D.; Lee, W. S.; Cho, S. D.; Yoon, Y. J. Synthesis 2003, 1517
  38. Kang, Y. J.; Chung, H. A; Kim, J. J.; Yoon, Y. J. Synthesis 2002, 733
  39. Park, Y. D.; Kim, J. J.; Chung, H. A; Kweon, D. H.; Cho, S. D.; Lee, S. G.; Yoon, Y. J. Synthesis 2003, 560
  40. Kweon, D. H.; Kim, H. K.; Kim, J. J.; Chung, H. A; Lee, W. S.; Kim, S. K.; Yoon, Y. H. J. J. Heterocyclic Chem. 2002, 39, 203 https://doi.org/10.1002/jhet.5570390129
  41. Chung, H. A.; Kweon, D. H.; Kang, Y. J.; Park, J. W.; Yoon, Y. J. J. Heterocyclic Chem. 1999, 36, 905 https://doi.org/10.1002/jhet.5570360413
  42. Kim, J. J.; Park, Y. D.; Kweon, D. H.; Kang, Y. J.; Kim, H. K.; Lee, S. G.; Cho, S. D.; Lee, W. S.; Yoon, Y. J. Bull. Kor. Chem. Soc. 2004, 25, 501 https://doi.org/10.5012/bkcs.2004.25.4.501
  43. 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
  44. Pence, E. L.; Langley, G. J.; Bugg, T. D. H. J. Am. Chem. Soc. 1996, 118, 8336 https://doi.org/10.1021/ja9607704
  45. Horaguchi, T.; Hosokawa, N. J. Heterocyclic Chem. 2002, 39, 61 https://doi.org/10.1002/jhet.5570390108
  46. Aldrich Hand Book of Fine Chemical; Sigma-Aldrich: 2007-2008; p 1879

Cited by

  1. ChemInform Abstract: Lactonization of ω-Hydroxycarboxylic Acids Using (4,5-Dichloro-6-oxo-6H-pyridazin-1-yl)phosphoric Acid Diethyl Ester vol.40, pp.13, 2009, https://doi.org/10.1002/chin.200913173
  2. Regiochemistry in Reaction of 4,5-Dichloro-2-cyanopyridazin-3(2H)-one with Nucleophiles vol.31, pp.4, 2008, https://doi.org/10.5012/bkcs.2010.31.04.1061
  3. Rapid and Effective Multihalogenations of 2,2',5',2"-Terthiophene with 2-Halo-4,5-dichloropyridazin-3(2H)-ones under Ambient Conditions vol.31, pp.10, 2008, https://doi.org/10.5012/bkcs.2010.31.10.2985
  4. Recent Progress in the Chemistry of Pyridazinones for Functional Group Transformations vol.83, pp.1, 2008, https://doi.org/10.1021/acs.joc.7b02481