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Reaction of some aromatic nitrile oxides with dimedone

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Chemistry of Heterocyclic Compounds Aims and scope

Abstract

1,3-Dipolar cycloaddition of benzonitrile and m-nitrobenzonitrile oxides to the enol form of dimedone gives the corresponding 4-oxotetrahydrobenzisoxazoles. A second reaction path — nucleophilic addition of the enol to the N-oxide to give a hydroxamic acid derivative — is observed in the case of m-nitrobenzonitrile oxide. The tetrahydrobenzisoxazoles are converted to enamine derivatives of benzoyldimedone under catalytic hydrogenation conditions.

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Literature cited

  1. A. Quilico and G. Speroni, Gazz. Chim. Ital., 76, 148 (1946).

    Google Scholar 

  2. R. Huisgen, Angew. Chem., 75, 613 (1963).

    Google Scholar 

  3. C. Grundmann and H. D. Frommeld, J. Org. Chem., 31, 157 (1966).

    Google Scholar 

  4. K. Nakanishi, Infrared Spectroscopy, Practical, Holden-Day, San Francisco (1962).

    Google Scholar 

  5. A. W. Crossley and N. Renouf, J. Chem. Soc., 101, 1524 (1912).

    Google Scholar 

  6. H. Smith, J. Chem. Soc., 803 (1953).

  7. A. A. Polyakova and A. A. Khmel'nitskii, Mass Spectrometry in Organic Chemistry [in Russian], Khimiya, Leningrad (1972), p. 268.

    Google Scholar 

  8. H. Budzikiewicz, C. Djerassi, and D. Williams, Interpretation of the Mass Spectra of Organic Compounds, Holden-Day (1964).

  9. R. Barnes, in: Heterocyclic Compounds [Russian translation], Vol. 5, Inostr. Lit. Moscow (1961), p. 377.

    Google Scholar 

  10. J. W. Scott and G. Saucy, J. Org. Chem., 37, 1652 (1972).

    Google Scholar 

  11. R. V. Stevens, C. G. Christensen, W. L. Edmonson, M. Kaplan, E. B. Reid, and M. P. Wentland, J. Amer. Chem. Soc., 93, 6629 (1971).

    Google Scholar 

  12. G. O. Dudek and G. P. Volpp, J. Org. Chem., 30, 50 (1965).

    Google Scholar 

  13. V. S. Bogdanov, V. V. Negrebetskii, F. A. Lakhvich, A. M. Moiseenkov, and A. A. Akhrem, Izv. Akad. Nauk SSSR, Ser. Khim., 1114 (1972).

  14. V. S. Bogdanov, V. V. Negrebetskii, V. A. Korenevskii, A. M. Moiseenkov, F. A. Lakhvich, and A. A. Akhrem, Izv. Akad. Nauk SSSR, Ser. Khim., 550 (1971).

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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 7, pp. 901–904, July, 1974.

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Akhrem, A.A., Khripach, V.A. & Lakhvich, F.A. Reaction of some aromatic nitrile oxides with dimedone. Chem Heterocycl Compd 10, 784–787 (1974). https://doi.org/10.1007/BF00471353

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  • DOI: https://doi.org/10.1007/BF00471353

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