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Phosphorylnitrile oxides. 5. Reactions of 3-(dialkoxyphosphoryl)isoxazoles and -isoxazolines with nucleophilic reagents

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Chemistry of Heterocyclic Compounds Aims and scope

Abstract

3-Phosphotylated isoxazoles and isoxazolines react with nucleophiles either with cleavage of the P-C bond and subsequent ring opening or with retention of the heterocyclic ring depending on the structure of the ring substituents, nature of the nucleophile, and reaction conditions. This permits the selective chemical modification of the starting compounds.

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References

  1. V. A. Pavlov, A. I. Kurdyukov, N. V. Aristova, B. I. Gorin, T. A. Zablikova, and V. V. Moskva, Zh. Obshch. Khim., 64 (1994).

  2. A. A. Akhrem, F. A. Lakhvich, and V. A. Khripach, Khim. Geterotsikl. Soedin., No. 9, 1155 (1981).

  3. F. A. Lakhvich, E. V. Koroleva, and A. A. Akhrem, Khim. Geterotsikl. Soedin., No. 4, 435 (1989).

  4. V. A. Pavlov, N. V. Aristova, and B. I. Gorin, Tenth Symposium on the Chemistry of Heterocyclic Compounds, Kosice, Czechoslovakia, Abstracts, Part II (1990), p. 69.

  5. N. V. Aristova, B. I. Gorin, S. V. Kovalenko, V. A. Pavlov, and V. V. Moskva, Khim. Geterotsikl. Soedin., No. 9, 1287 (1990).

  6. V. A. Pavlov, A. I. Kurdyukov, V. V. Plemenkov, R. R. Khaliuilin, and V. V. Moskva, Zh. Obshch. Khim.,63, 637 (1993).

    Google Scholar 

  7. D. Barton and W. D. Ollis (eds.), General Organic Chemistry [Russian translation], Vol. 9, Khimiya, Moscow (1985), p. 489.

    Google Scholar 

  8. D. Redvore, J. Org. Chem.,35, 4114 (1970).

    Google Scholar 

  9. N. K. Kochetkov and S. D. Sokolov, Zh. Obshch. Khim.,33, 1442 (1963).

    Google Scholar 

  10. M. I. Shevchuk, A. F. Tolochko, M. G. Bal'on, and M. V. Khalaturnik, Zh. Org. Khim., 14, 2003 (1978).

    Google Scholar 

  11. V. Jager and H. Grund, Angew. Chem.,88, 27 (1976).

    Google Scholar 

  12. P. Cardirola, M. Ciancaglione, M. Amici, and C. Micheli, Tetrahedron Lett.,27, 4647 (1986).

    Google Scholar 

  13. L. I. Deiko and K. V. Varlygo, “Study of glutamatergic synapses. Theoretical and applied aspects,” in: Yu. E. Mandel'shtam (ed.), Proceedings of the All-Union Conference on the Physiology and Biochemistry of Glutamatergic Synapses. Nauka, Leningrad (1989), p. 25.

    Google Scholar 

  14. H. H. Hussain, Synthetic and Mechanistic Studies Relating to Halogenated Cyclopropanes and Cyclopropenes, Ph.D. Thesis, University of Newcastle, United Kingdom (1987).

    Google Scholar 

  15. M. P. Sokolov, B. I. Buzykin, and V. A. Pavlov, Zh. Obshch. Khim.,60, 223 (1990).

    Google Scholar 

  16. R. R. Shagidullin, V. A. Pavlov, B. I. Buzykin, N. V. Aristova, L. F. Chertanova, I. I. Bandyukova, A. Kh. Plyamovatyi, K. M. Enikeev, M. P. Sokolov, and V. V. Moskva, Zh. Obshch. Khim.,61, 1590 (1991).

    Google Scholar 

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Kazan State Technological University, Kazan 420015. Institute of Physiologically Active Compounds, Russian Academy of Sciences, Chernogolovka 142432. A. I. Gertsen Russian State Pedogogical University, St. Petersburg 191186. Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 6, pp. 821–828, June, 1994. Original article submitted April 28, 1994.

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Pavlov, V.A., Kurdyukov, A.I., Gorin, B.I. et al. Phosphorylnitrile oxides. 5. Reactions of 3-(dialkoxyphosphoryl)isoxazoles and -isoxazolines with nucleophilic reagents. Chem Heterocycl Compd 30, 718–723 (1994). https://doi.org/10.1007/BF01166315

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