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Some Chemical Transformations of 4,5-Dihydro-5-methyl-3H-spiro[benz-2-azepine-3,1'-cyclohexane] N-Oxide

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Chemistry of Heterocyclic Compounds Aims and scope

Abstract

The oxidation and reduction of 4,5-dihydro-5-methyl-3H-spiro[benz-2-azepine-3,1'-cyclohexane] N-oxide, the reactions of this N-oxide with methylmagnesium iodide, the sodium salt of diethyl malonate, phenyl isocyanate, and its rearrangement by the action of acetic anhydride lead to N-hydroxy-1,2,3,4-tetrahydrobenz-2-azepines, benz-2-azepine-1-one, and its N-acetoxy derivative as well as isoxazolidino- and oxadiazolidino[3,2-a]benz-2-azepines spirofused with a cyclohexane ring.

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REFERENCES

  1. J. Hamer and A. Macaluso, Chem. Rev., 64, 473 (1964).

    Google Scholar 

  2. D. St. C. Black, R. F. Crozier, and V. C. Davis, Synthesis, 205 (1975).

  3. R. C. Bernotas, G. Adams, and A. Carr, Tetrahedron, 52, 6519 (1996).

    Google Scholar 

  4. V. Kouznetsov, A. R. Palma, S. Salas, L. Y. Vargas, F. Zubkov, A. Varlamov, and J. R. Martinez, J. Heterocycl. Chem., 34, 1591 (1997).

    Google Scholar 

  5. A. V. Varlamov, F. I. Zubkov, K. F. Turchin, A. I. Chernyshev, and R. S. Borisov, Khim. Geterotsikl. Soedin., 1360 (2001).

  6. A. V. Varlamov, F. I. Zubkov, A. I. Chernyshev, and N. M. Mikhailov, Abstracts of the Third All-Russian Congress on Man and Pharmaceuticals [in Russian], Farmmedinfo, Moscow (1996), p. 13.

  7. A. V. Varlamov, K. F. Turchin, A. I. Chernyshev, F. I. Zubkov, and T. N. Borisova, Khim. Geterotsikl. Soedin., 703 (2000).

  8. A. V. Varlamov, D. G. Grudinin, A. I. Chernyshev, A. N. Levov, N. I. Golovtsov, and R. S. Borisov, Khim. Geterotsikl. Soedin., 376 (2001).

  9. V. S. Shklyaev, B. B. Aleksandrov, M. S. Gavrilov, and A. G. Mikhailovskii, in: Enamines in Organic Synthesis [in Russian], Urals Branch, Academy of Sciences of the USSR, Sverdlovsk (1989), p. 80.

  10. S. Ozaki, Chem. Rev., 72, 457 (1972).

    Google Scholar 

  11. H. Stamm and J. Hoenicke, Liebigs Ann. Chem., 478, 143 (1971).

    Google Scholar 

  12. M. Lamchen, in: B. S. Thyagarajan (editor), Mechanisms of Molecular Migrations, Vol. 1, Interscience, New York, (1968), p. 36.

    Google Scholar 

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Varlamov, A.V., Grudinin, D.G. & Chernyshev, A.I. Some Chemical Transformations of 4,5-Dihydro-5-methyl-3H-spiro[benz-2-azepine-3,1'-cyclohexane] N-Oxide. Chemistry of Heterocyclic Compounds 40, 622–630 (2004). https://doi.org/10.1023/B:COHC.0000037318.38320.7b

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  • DOI: https://doi.org/10.1023/B:COHC.0000037318.38320.7b

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