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Preparation of O-Alkylhydroxamic Acids Using 2-Acylpyridazin-3(2H)-ones in Water

  • Kim, Jeum-Jong (Department of Chemistry and Environmental Biotechnology National Core Research Center, Gyeongsang National University) ;
  • Park, Yong-Dae (Department of Chemistry and Environmental Biotechnology National Core Research Center, Gyeongsang National University) ;
  • Cho, Su-Dong (Research Institute of Basic Science, Changwon National University) ;
  • Kim, Ho-Kyun (Department of Chemistry and Environmental Biotechnology National Core Research Center, Gyeongsang National University) ;
  • Kang, Young-Jin (Department of Chemistry and Environmental Biotechnology National Core Research Center, Gyeongsang National University) ;
  • Lee, Sang-Gyeong (Department of Chemistry and Research Institute of Life Science, Gyeongsang National University) ;
  • Falck, J.R. (Department of Biochemistry, University of Texas Southwestern Medical Center) ;
  • Shiro, Motoo (Rigaku Corporation) ;
  • Yoon, Yong-Jin (Department of Chemistry and Environmental Biotechnology National Core Research Center, Gyeongsang National University)
  • Published : 2004.08.20
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References

  1. Whittaker, M.; Floyd, C. D.; Brown, P.; Gearing, A. J. H. Chem. Rev. 1999, 99, 2735. https://doi.org/10.1021/cr9804543
  2. Caldarelli, M.;Habermann, J.; Ley, S. V. Bioorg. Med. Chem. Lett. 1999, 9, 2049. https://doi.org/10.1016/S0960-894X(99)00311-X
  3. Finnin, M. S.; Donigian, J. R.; Cohen, A.; Richon, V. M.;Rifkind, R. A.; Marks, P. A.; Breslow, R.; Pavletich, N. P. Nature1999, 401, 188. https://doi.org/10.1038/43710
  4. Miller, T. A.; Witter, D. J.; Belvedere, S. J.Med. Chem. 2003, 46, 5097. https://doi.org/10.1021/jm0303094
  5. Kim, D. K.; Lee, J. Y.; Kim, J. S.;Ryu, J. H.; Choi, J. Y.; Lee, J. W.; Im, G. J.; Kim, T. K.; Seo, J. W.;Park, H. J.; Yoo, J.; Park, J. H.; Kim, T. U.; Bang, Y. J. J. Med.Chem. 2003, 46, 5745. https://doi.org/10.1021/jm030377q
  6. Lu, Q.; Yang, Y.-T.; Chen, C.-S.; Davis,M.; Byrd, J. C.; Etherton, M. R. J. Med. Chem. 2004, 47, 467. https://doi.org/10.1021/jm0303655
  7. Roosenberg II, J. M.; Miller, M. J. J. Org. Chem. 2000, 65,4833. https://doi.org/10.1021/jo000050m
  8. Gaspar, M.; Granzina, R.; Bodor, A.; Farkas, E.; Santos,M. A. J. Chem. Soc. Dalton Trans. 1999, 799.
  9. Lin, Y.-M.;Miller, M. J. J. Org. Chem. 1999, 64, 7451. https://doi.org/10.1021/jo990769y
  10. Wang, Q. X.;Phanstiel IV, O. J. Org. Chem. 1998, 63, 1491. https://doi.org/10.1021/jo9717144
  11. Xu, Y.; Miller,M. J. J. Org. Chem. 1998, 63, 4314. https://doi.org/10.1021/jo980063o
  12. Sakamoto, T.; Li, H.;Kikugawa, Y. J. Org. Chem. 1996, 61, 8496. https://doi.org/10.1021/jo961458f
  13. iller, M. J. Chem. Rev. 1989, 89, 1563. https://doi.org/10.1021/cr00097a011
  14. Bergeron, R. J.;Wiegand, J.; McManis, J. S.; Perumal, P. T. J. Med. Chem. 1991,34, 3182. https://doi.org/10.1021/jm00115a006
  15. Sandler, S. P.; Karo, W. In Organic Functional GroupPreparations, Vol. III; Academic Press: New York, 1972; p 406.
  16. Koshiti, N.; Reddy, G. V.; Jacobs, H.; Gopalan, A. Synth.Commun. 2002, 32, 3779. https://doi.org/10.1081/SCC-120015396
  17. Bailen, M. A.; Chinchilla, R.;Dodsworth, D. J.; Najera, C. Tetrahedron Lett. 2001, 42, 5013. https://doi.org/10.1016/S0040-4039(01)00923-6
  18. Fray, M. J.; Burslm, M. F.; Dicknson, R. P. Bioorg. Med. Chem.Lett. 2001, 11, 567. https://doi.org/10.1016/S0960-894X(00)00719-8
  19. Dankwardt, S. M.; Billedeau, R. J.;Lawley, L. K.; Abbot, S. C.; Martin, R. L.; Chan, C. S.; Van Wart,H. E.; Walker, K. A. M. Bioorg. Med. Chem. Lett. 2000, 10, 2513. https://doi.org/10.1016/S0960-894X(00)00525-4
  20. Nikam, S. S.; Kronberg, B. E.; Johnson, D. R.; Doherty, A. M.Tetrahedron Lett. 1995, 36, 197. https://doi.org/10.1016/0040-4039(94)02246-8
  21. Altenburger, J. M.;Mioskowski, C.; d'Orchymont, H.; Schirlin, D.; Schalk, C.;Tarnus, C. Tetrahedron Lett. 1992, 33, 5055. https://doi.org/10.1016/S0040-4039(00)61187-5
  22. Pirrung, M. C.;Chang, J. H. L. J. Org. Chem. 1995, 60, 8084. https://doi.org/10.1021/jo00129a059
  23. Barlaam, B.;Harmon, A.; Maudet, M. Tetrahedron Lett. 1998, 39, 7865. https://doi.org/10.1016/S0040-4039(98)01760-2
  24. Ando, W.; Tsumaki, H. Synth. Commun. 1983, 13, 1053. https://doi.org/10.1080/00397918308082726
  25. Lee,B. H.; Miller, M. J. J. Org. Chem. 1983, 48, 24. https://doi.org/10.1021/jo00149a005
  26. King, F. D.;Pike, S.; Walton, D. R. M. J. Chem. Soc. Chem. Commun. 1978,351.
  27. Sibi, M. P.; Hasegawa, H.; Ghorpade, S. R. Org. Lett. 2002, 4,3343. https://doi.org/10.1021/ol0263301
  28. Kang, Y. J.; Chung, H. A.; Kim, J. J.; Yoon, Y. J. Synthesis 2002,733.
  29. Park, Y. D.; Kim, J. J.; Chung, H. A.; Kweon, D. H.; Cho, S. D.;Lee, S. G.; Yoon, Y. J. Synthesis 2003, 560.
  30. 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
  31. Kim, H.K.; Park, Y. D.; Kim, J. J.; Lee, M. H.; Chung, H. A.; Kweon, D.H.; Cho, S. D.; Yoon, Y. J. Bull. Korean Chem. Soc. 2003, 24,1655. https://doi.org/10.5012/bkcs.2003.24.11.1655
  32. Kim, J. J.; Park, Y. D.; Lee, W. S.; Cho, S. D.; Yoon, Y. J.Synthesis 2003, 1517.
  33. Kweon, D. H.; Kim, H. K.; Kim, J. J.;Chung, H. A.; Lee, W. S.; Kim, S. K.; Yoon, Y. J. J. HeterocyclicChem. 2002, 39, 203. https://doi.org/10.1002/jhet.5570390129
  34. 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
  35. Organic Synthesis in Water; Grieco, P. A., Ed.; Blakie Academic and Professional: London, 1998.
  36. Li, C. J. Chem. Rev. 1993, 93,2023.
  37. Manabe, K.; Kobayasi, S. Chem.-Eur. J. 2002, 8, 4094. https://doi.org/10.1002/1521-3765(20020916)8:18<4094::AID-CHEM4094>3.0.CO;2-G
  38. Corma, A.; Garcia, H. Chem. Rev. 2003, 103, 4307. https://doi.org/10.1021/cr030680z
  39. SIR97: Altomare, A.; Burla, M.; Camalli, M.; Cascarano, G.;Giacovazzo, C.; Guagliardi, A.; Moliterni, A.; Polidori, G.;Spagna, R. J. Appl. Cryst. 1999, 32, 115. https://doi.org/10.1107/S0021889898007717
  40. DIRDIF99: Beurskens, P. T.; Admiraal, G.; Beurskens, G.; Bosman,W. P.; de Gelder, R.; Israel, R.; Smits, J. M. M. The DIRDIF-99Program System, Technical Report of the CrystallographyLaboratory; University of Nijmegen: The Netherlands, 1999.
  41. Flack, H. D. Acta Cryst. 1983, A39, 876-881.
  42. Cromer, D. T.; Waber, J. T. International Tables for X-rayCrystallography, Vol. IV; The Kynoch Press: Birmingham,England, 1974; Table 2.2 A.
  43. Ibers, J. A.; Hamilton, W. C. Acta Crystallogr. 1964, 17, 781. https://doi.org/10.1107/S0365110X64002067
  44. Creagh, D. C.; McAuley, W. J. International Tables for Crystallography,Vol C; Wilson, A. J. C., Ed.; Kluwer Academic Publishers:Boston, 1992; pages 219-222, Table 4.2.6.8.
  45. Creagh, D. C.; Hubbell, J. H. International Tables for Crystallography,Vol C; Wilson, A. J. C., Ed.; Kluwer Academic Publishers:Boston, 1992; pages 200-206, Table 4.2.4.3.
  46. CrystalStructure 3.6.0: Crystal Structure Analysis Package;Rigaku and Rigaku/MSC: 9009 New Trails Dr. The Woodlands,TX 77381, USA, 2000-2004.
  47. Watkin, D. J.; Prout, C. K.; Carruthers, J. R.; Betteridge, P. W. CRYSTALS, Issue 10; Chemical Crystallography Laboratory: Oxford, UK, 1996.

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