Bulletin of the Korean Chemical Society

  • 제32권12호
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  • Pages.4176-4178
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  • 2011
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  • 0253-2964(pISSN)
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  • 1229-5949(eISSN)
대한화학회 (Korean Chemical Society)
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Synthesis of Isoxazolone Derivatives from (Chlorocarbonyl)phenyl Ketene with Benzhydroxamic Acids

  • Nejadshafiee, Vajihe (Department of Chemistry, Shahid Bahonar University of Kerman) ;
  • Saidi, Kazem (Department of Chemistry, Shahid Bahonar University of Kerman) ;
  • Abaszadeh, Mehdi (Department of Chemistry, Shahid Bahonar University of Kerman)
  • 투고 : 2011.07.30
  • 심사 : 2011.09.26
  • 발행 : 2011.12.20
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초록

The reaction of (chlorocarbonyl)phenyl ketene, with readily available benzhydroxamic acid derivatives, such as benzhydroxamic acid, 4-chlorobenzhydroxamic acid, 3-nitrobenzhydroxamic acid, 4-methylbenzhydroxamic acid, N-hydroxy-3-oxo-3-phenylpropionamide, N-hydroxy-2-phenylacetamide, affords isoxazolone derivatives in high yields in a one step procedure. The formation of the products proceeds by a mechanism, that involves replacement of chlorine of the ketene, by benzhydroxamic acids, followed by rapid ring closure of this intermediate to form isoxazolone derivatives.

키워드

참고문헌

  1. Islami, M. R.; Allen, A. D.; Vokovic, S.; Tidwell, T. T. Org. Lett. 2011, 13, 494. https://doi.org/10.1021/ol102837n
  2. Staudinger, H. Ber. Dtsch. Chem. Ges. 1905, 38, 1735. https://doi.org/10.1002/cber.19050380283
  3. Staudinger, H. From Organic Chemistry to Macromolecules; Wiley: New York, 1970.
  4. Tidwell, T. T. Angew. Chem. Int. Ed. 2005, 44, 5778. Herman Staudinger von Nobel Prize in 1953. https://doi.org/10.1002/anie.200500098
  5. Brady, W. T. Synthesis 1971, 415, 422.
  6. Saidi, K.; Tidwell, T. T. Arkivoc. 2001, xii, 100.
  7. Nakanishi, S.; Butler, K. Organic Preparations and Procedures Int. 1975, 7, 155. https://doi.org/10.1080/00304947509355137
  8. Saidi, K.; Shaterian, H. R.; Sheibani, H. Synth. Commun. 2000, 30, 2345. https://doi.org/10.1080/00397910008086875
  9. Saidi, K.; Sheibani, H. Synth. Commun. 2001, 31, 1809. https://doi.org/10.1081/SCC-100104328
  10. Tikdari, A. M.; Shokrani, A.; Hamidian, H.; Kabazzadeh, H. J. Chin. Chem. Soc. 2005, 52, 1153.
  11. Potts, K. T.; Kanemass, S.; Zvillichovsky, G. J. Am. Chem. Soc. 1980, 3971.
  12. Brown, D. G.; Hoye, T. R.; Brisbois, R. G. J. Org. Chem. 1998, 63, 1630. https://doi.org/10.1021/jo9719315
  13. Padwa, A.; Coats, S. J.; Harring, S. R.; Hadjiarapoglou, L.; Semones, M. A. Synthesis 1995, 973.
  14. Potts, K. T.; Ehlinger, R.; Nichols, W. M. J. Org. Chem. 1975, 40, 2596. https://doi.org/10.1021/jo00906a005
  15. Sheibani, H.; Lari, J.; Islami, M. R.; Saidi, K. Russian Chemical Bullentin International Edition. 2003, 52, 6, 1411. https://doi.org/10.1023/A:1024843614755
  16. Sheibani, H.; Islami, M. R.; Khabazzadeh, H.; Saidi, K. Tetrahedron. 2004, 60, 5931. https://doi.org/10.1016/j.tet.2004.05.025
  17. Abaszadeh, M.; Sheibani, H.; Saidi, K. Aust. J. Chem. 2010, 63, 92. https://doi.org/10.1071/CH09344
  18. Sheibani, H.; Mosslemin, M. H.; Behzadi, S.; Islami, M. R.; Foroughi, H.; Saidi, K. Arkivoc. 2005, XV, 88.
  19. Sheibani, H.; Mosslemin, M. H.; Behzadi, S.; Islami, M. R.; Saidi, K. Synthesis 2005, 435.
  20. Hauser, C. R.; Renfrom, W. B. Organic Syntheses 1943, 2, 67.

피인용 문헌

  1. A one-pot reaction of (chlorocarbonyl) phenyl ketene with β-ketoamides and thiochromen-2-one vol.10, pp.2, 2013, https://doi.org/10.1007/s13738-012-0146-8
  2. Ketenes and Other Cumulenes as Reactive Intermediates vol.113, pp.9, 2013, https://doi.org/10.1021/cr3005263