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Synthesis of 3-aryl-5-diethoxyphosphorylethyne-4,5-dihydroisoxazoles

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Chemistry of Heterocyclic Compounds Aims and scope

A convenient preparative method has been developed for obtaining a vinylacetylene phosphonate. The reaction of arylnitrile oxides with 4-(diethylphosphoryl)-2-methylbut-1-en-3-yne proceeds as a regioselective 1,3-dipolar cycloaddition exclusively at the terminal double bond of vinylacetylene phosphonate.

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References

  1. J. S. D. Kurmar, M. M. Ho, J. M. Leung, and T. Toyokuni, Adv. Synth. Catal., 344, 1146 (2002).

    Article  Google Scholar 

  2. Y. Hagiwara, M. Tanaka, A. Kajitani, and S. Yasumoto, Jpn. Pat. Appl. 3220180; Chem. Abstr., 116, 128944s (1992).

    Google Scholar 

  3. N. Minami, M. Sato, K. Hasumi, N. Yamamoto, K. Keino, T. Matsui, A. Kaneda, S. Ota, N. Saitou, S. Sato, A. Asau, S. Doi, M. Kobayashi, J. Sato, and S. Asano, Jpn. Pat. Appl. 2000086657; Chem. Abstr., 132, 251139r (2000).

    Google Scholar 

  4. O. Dannhardt, P. Dominiak, and S. Laufer, Arzneim. Forsch., 43, 441 (1993).

    CAS  Google Scholar 

  5. P. Skolnick, J. Clin. Psychiatry, 63, 19 (2002).

    CAS  Google Scholar 

  6. A. J. Scheen and M. Malaise, Rev. Med. Liege, 59, 251 (2004).

    CAS  Google Scholar 

  7. Q. Chen, F. Liu, F. Xu, and C. Yang, J. Heterocycl. Chem., 45, 77 (2008).

    Article  CAS  Google Scholar 

  8. R. Eskandari, L. Navidpour, M. Amini, H. Shafaroodi, and A. Shafiee, J. Heterocycl. Chem., 44, 449 (2007).

    Article  CAS  Google Scholar 

  9. E. de Clercq, Biochem. Pharmacol., 82, 99 (2011).

    Article  Google Scholar 

  10. V. K. Brel, Heteroat. Chem., 17, 547 (2006).

    Article  CAS  Google Scholar 

  11. V. K. Brel, Synthesis, 2674 (2007).

  12. V. K. Brel, Synthesis, 3405 (2009).

  13. V. K. Brel, V. K. Belsky, A. I. Stash, V. E. Zavodnik, and P. J. Stang, Org. Biomol. Chem., 1, 4220 (2003).

    Article  CAS  Google Scholar 

  14. V. K. Brel, Synthesis, 463 (1999).

  15. K.-C. Liu, B. R. Shelton, and R. K. Howe, J. Org. Chem., 45, 3916 (1980).

    Article  CAS  Google Scholar 

  16. T. Olsson, K. Stern, and S. Sundell, J. Org. Chem., 53, 2468 (1988).

    Article  CAS  Google Scholar 

  17. A. Weissberger, E. Proskauer, J. A. Riddick, and E. E. Toops, Jr., Organic Solvents, Wiley-Interscience, New York (1955).

    Google Scholar 

Download references

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Correspondence to V. K. Brel’.

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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 6, pp. 977-981, June, 2012.

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Brel’, V.K. Synthesis of 3-aryl-5-diethoxyphosphorylethyne-4,5-dihydroisoxazoles. Chem Heterocycl Comp 48, 907–911 (2012). https://doi.org/10.1007/s10593-012-1075-2

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  • DOI: https://doi.org/10.1007/s10593-012-1075-2

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