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The synthesis of new 5-aminoisoxazoles by reaction of thiocarbamoylcyanoacetates with hydroxylamine

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Abstract

The reaction of thiocarbamoylcyanoacetates with hydroxylamine in ethanol under reflux conditions has provided a convenient method for the synthesis of 5-aminoisoxazoles.

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References

  1. For a brief Review see: L. Carlsen, D. Dopp, H. Dopp, F. Duus, H. Hartmann, S. Lang-Fugmann, B. Schulze, R. K. Smalley, and B. J. Wakefield, in: E. Schaumann (editor), Houben-Weyl, Methods in Organic Chemistry; Georg Thieme Verlag, Stuttgart, Germany, 1992, Vol. E 8a, p. 45.

    Google Scholar 

  2. M. Rowley, H. B. Broughton, I. Collins, R. Baker, F. Emms, R. Marwood, S. Patel, and C. I. Ragan, J. Med. Chem., 39, 1943 (1996).

    Article  CAS  Google Scholar 

  3. B. Frolund, A. T. Jorgensen, L. Tagmose, T. B. Stensbol, H. T. Vestergaard, C. Engblom, U. Kristiansen, C. Sanchez, P. Krogsgaard-Larsen, and T. Liljefors, J. Med. Chem., 45, 2454 (2002).

    Article  CAS  Google Scholar 

  4. G. Daidone, D. Raffa, B. Maggio, F. Plescia, V. M. C. Cutuli, N. G. Mangano, and A. Caruso, Arch. Pharm. Med. Chem., 332, 50 (1999).

    Article  CAS  Google Scholar 

  5. K. Tomita, Y. Takahi, R. Ishizuka, S. Kamamura, M. Nakagawa, M. Ando, T. Nakanishi, and T. Nakamura, H. Udaira, Ann. Sankyo Res. Lab., 1, 25 (1973); Chem. Abstr., 80, 120808 (1974).

    Google Scholar 

  6. J. J. Talley, Prog. Med. Chem., 13, 201 (1999).

    Article  Google Scholar 

  7. J. J. Talley, D. L. Brown, J. S. Carter, M. J. Graneto, C. M. Koboldt, J. L. Masferrer, W. E. Perkins, R. S. Rogers, A. F. Shaffer, Y. Y. Zhang, B. S. Zweifel, and K. Seibert, J. Med. Chem., 43, 775 (2000).

    Article  CAS  Google Scholar 

  8. M. P. Giovannoni, C. Vergelli, C. Ghelardini, N. Galeotti, A. Bartolini, and V. Kal Piaz, J. Med. Chem., 46, 1055 (2003).

    Article  CAS  Google Scholar 

  9. W. T. Li, D. R. Hwang, C. P. Chen, C. W. Shen, C. L. Huang, T. W. Chen, C. H. Lin, Y. L. Chang, Y. Y. Chang, Y. K. Lo, H. Y. Tseng, C. C. Lin, J. S. Song, H. C. Chen, S. J. Chen, S. H. Wu, C. T. Chen, J. Med. Chem., 46, 1706 (2003).

    Article  CAS  Google Scholar 

  10. For a recent Review, see: B. J. Wakefield, in: E. Shaumann (editor), Science of Synthesis: Houben-Weyl Methods of Molecular Transformations, Georg Thieme Verlag, Stuttgart, 2001, vol. 11, p. 229.

    Google Scholar 

  11. T. Bandiera, T. P. Grunanger, and F. M. Albini, J. Heterocycl. Chem., 29, 1423 (1992).

    CAS  Google Scholar 

  12. P. Cuadrado, A. M. Gonzalez-Nogal, and R. Valero, Tetrahedron, 58, 4975 (2002).

    Article  CAS  Google Scholar 

  13. C. B. Vicentini, A. C. Verones, T. Poli, M. Guarneri, P. Giori, and V. Ferretti, J. Heterocycl. Chem., 27, 1481 (1990).

    CAS  Google Scholar 

  14. Y. He and N. H. Lin, Synthesis, 9, 989 (1994).

    Article  Google Scholar 

  15. G. N. Barber and R. A. Olofson, J. Org. Chem., 43, 3015 (1978).

    Article  CAS  Google Scholar 

  16. T. J. Nitz, D. L. Volkots, D. J. Aldous, and R. C. Oglesby, J. Org. Chem., 59, 5828 (1994).

    Article  CAS  Google Scholar 

  17. S. E. Denmark and J. M. Kallemeyn, J. Org. Chem., 70, 2839 (2005).

    Article  CAS  Google Scholar 

  18. V. Jaeger and P. A. Colinas, in: A. Padwa and W. H. Pearson (editors), Synthetic Applications of 1,3-Dipolar Cycloaddition Chemistry Toward Heterocycles Natural Products, Chemistry of Heterocyclic Compounds, Wiley, Hoboken, 2002, vol. 59, p. 361.

    Chapter  Google Scholar 

  19. J. Khalafy, A. R. Molla Ebrahimlo, R. Eisavi, and K. Akbari Dilmaghani, ARKIVOC, xiv, 59 (2005).

  20. J. Khalafy, A. Poursattar Marjani, and A. R. Molla Ebrahimlo, J. Braz. Chem. Soc., 17, 570 (2006).

    Article  CAS  Google Scholar 

  21. M. M. Baradarani, J. Khalafy, S. Khadivi, and A. Poursattar Marjani, XTC, 751 (2008). [Chem. Heterocycl. Comp., 44 (2008)].

    Google Scholar 

  22. D. E. Worrall, J. Am. Chem. Soc., 45, 3092 (1923).

    Article  CAS  Google Scholar 

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Correspondence to J. Khalafy.

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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 6, pp. 907–912, June, 2008.

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Khalafy, J., Akbari Dilmaghani, K., Soltani, L. et al. The synthesis of new 5-aminoisoxazoles by reaction of thiocarbamoylcyanoacetates with hydroxylamine. Chem Heterocycl Comp 44, 729–734 (2008). https://doi.org/10.1007/s10593-008-0101-x

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  • DOI: https://doi.org/10.1007/s10593-008-0101-x

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