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Reaction of aryl-β-nitrovinyl ketones with hydrogen halides. Preparation of isoxazoles

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Chemistry of Heterocyclic Compounds Aims and scope

Abstract

A study is made of the reactions of aryl-β-nitrovinyl ketones with hydrogen chloride, hydrogen bromide, and hydriodic acid. It is shown that reaction leads to cyclization forming substituted isoxazoles, and that with hydrogen bromide and hydriodic acid, cyclization is accompanied by reduction. The action of hydrogen chloride on phenyl-β-nitrovinyl ketone gives 3, 4-dichloro-5-phenylisoxazole, while hydrogen bromide gives 5-phenyl- and 3-bromo-5-phenylisoxazoles, and hydriodic acid 5-phenylisoxazole. Chlorination of 3-chioro-5-phenylisoxazole and bromination of 3-bromo-5-phenyl-isoxazole are methods of synthesizing 3, 4-dichloro- and 3, 4-dibromo-5-phenylisoxazole, respectively. The general equations for the reactions are given.

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References

  1. M. I. Rybinskaya, L. V. Rybin, and A. N. Nesmeyanov, Izv. AN SSSR, OKhN, 899, 1963.

  2. A. N. Nesmeyanov, M. I. Rybinskaya, and L. V. Rybin, Izv. AN SSSR, ser. khim., 1382, 1965.

  3. P. Bravo, G. Gaudiano, A. Quilico, and A. Ricca, Gazz., 91, 47, 1961.

    Google Scholar 

  4. T. L. Cairns, and B. C. McKusick, Angew. Chem., 73, 520, 1961.

    Google Scholar 

  5. R. L. Heath and J. D. Rose, J, Chem. Soc., 1485, 1947.

  6. M. F. Hawthorne, J. Am. Chem. Soc., 79, 2150, 1957.

    Google Scholar 

  7. N. Kornblum and R. A. Brown, J. Am. Chem.Soc., 87, 1742, 1965.

    Google Scholar 

  8. R. Fusco and S. Rossi, Chem. a. Ind., 1957, 1650; Rend. Ist. lombardo sci. e lettere. Sci. mat., fis., chim. e geol., 94, 729, 729; 1960, RZhKh, 6Zh, 257, 1963.

  9. A. N. Nesmeyanov and R. V. Golovnya, DAN, 133, 1337, 1960; ZhOKh, 31, 1067, 1961.

    Google Scholar 

  10. N. C. Deno, N. Friedman, J. D. Hodge, F. P. Mac Kay, and G. Saines, J. Am. Chem. Soc., 84, 4713, 1962.

    Google Scholar 

  11. S. S. Novikov, V. V. Sevost'yanova, and A. A. Fainzil'berg, Usp. khim., 31, 1417, 1962.

    Google Scholar 

  12. A. R. Katritzky and A. J. Boulton, Spectrochim. Acta, 17, 238, 1961.

    Google Scholar 

  13. S. D. Sokolov, L. A. Kazitsyna, and L. K. Guseva, ZhOrKh, 2, 731, 1966.

    Google Scholar 

  14. N. K. Kochetkov and E. D. Khomutova, ZhOKh, 28, 359, 1958.

    Google Scholar 

  15. N. K. Kochetkov, E. D. Khomutova, M. Ya. Karpeiskii, and A. Ya. Khorlin, ZhOKh, 27, 452, 1957.

    Google Scholar 

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Authors and Affiliations

  1. Institute of Chemistry of Hetero-Organic Compounds, AS USSR, USSR

    A. N. Nesmeyanov, L. V. Rybin, M. I. Rybinskaya & S. D. Sokolov

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  1. A. N. Nesmeyanov
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  2. L. V. Rybin
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  3. M. I. Rybinskaya
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  4. S. D. Sokolov
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Nesmeyanov, A.N., Rybin, L.V., Rybinskaya, M.I. et al. Reaction of aryl-β-nitrovinyl ketones with hydrogen halides. Preparation of isoxazoles. Chem Heterocycl Compd 3, 633–636 (1967). https://doi.org/10.1007/BF00468331

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