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Oxidation of 1-hydrazino-3,3-dimethyl-3,4-dihydroisoquinoline. X-ray, spectroscopic, and quantum-chemical study of the structure of 3,3-dimethyl-3,4-dihydroisocarbostyryl azine

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Abstract

3,3-Dimethyl-3,4-dihydroisocarbostyryl azine (2) has been synthesized by oxidation of l-hydrazino-3,3-dimethyl-3,4-dihydroisoquinoline (1). The crystal and molecular structures of compound 2 were determined. It has been established that in the solid state, compound2 exists as an azine tautomer. The IR, electronic, and NMR spectral data indicate that in solution the tautomeric form of2 does not change. A possible mechanism of the oxidation of1 to2 is suggested.

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References

  1. A. B. Aleksandrov, V. A. Glushkov, E. N. Glushkova, A. A. Gorbunov, V. S. Shklyaev, and Yu. V., Shklyaev,Khim. Geterotsikl. Soedin., 1994, 511 [J. Chem. Heterocycl. Compd., 1994 (Engl. Transl.)].

  2. M. Tishler and B. Stanovnik,Khim. Geterotsikl. Soedin., 1980, 579 [Chem. Heterocycl. Compd., 1980 (Engl. Transl.)].

  3. E. M. Gizatullina and V. G. Kartsev,Khim. Geterotsikl. Soedin., 1993, 1587 [Chem. Heterocycl. Compd., 1993 (Engl. Transl.)].

  4. V. V. Davydov, V. I. Sokol, E. V. Balebanova, V. K. Belyaeva, Yu. V. Shklyaev, I. N. Marov, B. E. Zaitsev, and M. A. Porai-Koshits,Koord. Khim., 1993,19, 803 [J. Coord. Chem., 1993,19 (Engl. Transl.)].

    Google Scholar 

  5. V. V. Davydov, V. I. Sokol, E. V. Balebanova, Yu. V. Shklyaev, S. V. Sergeev, V. A. Nikanorov, B. E. Zaitsev, and M. A. Porai-Koshits,Izv. Akad. Nauk, Ser. Khim., 1993, 331 [Russ. Chem. Bull., 1993,42, 288 (Engl. Transl.)].

    Google Scholar 

  6. V. I. Sokol, V. V. Davydov, E. V. Balebanova, M. A. Porai-Koshits, Yu. V. Shklyaev, and B. E. Zaitsev,Koord. Khim., 1995,21, 325 [J. Coord. Chem., 1995,21 (Engl. Transl.)].

    Google Scholar 

  7. V. I. Sokol, V. V. Davydov, E. V. Balebanova, M. A. Porai-Koshits, Yu. V. Shklyaev, and B. E. Zaitsev,Koord. Khim., 1995,21, 413 [J. Coord. Chem., 1995,21 (Engl. Transl.)].

    Google Scholar 

  8. L. J. Bellamy,The Infra-red Spectra of Complex Molecules, J. Wiley and Sons, Inc., New York, London, 1954.

    Google Scholar 

  9. A. V. Johansen, inVodorodnaya svyaz' [The Hydrogen Bond], Ed. N. D. Sokolov, Nauka, Moscow, 1981, 134 (in Russian).

    Google Scholar 

  10. V. S. Shklyaev, B. B. Aleksandrov, G. I. Legotkina, M. I. Vakhrin, M. S. Gavrilov, and A. G. Mikhailovskii,Khim. Geterotsikl. Soedin., 1983, 1560 [Chem. Heterocycl. Compd., 1983 (Engl. Transl.)].

  11. B. Yoshio, E. Osamu, and T. Masanao,Chem. Pharm. Bull., 1960,8, 194.

    Google Scholar 

  12. O. V. Sverdlova,Elektronnye spektry v organicheskoi khimii [Electronic Spectra in Organic Chemistry], Khimiya, Leningrad, 1985 (in Russian).

    Google Scholar 

  13. Yu. P. Kitaev and B. I. Buzykin,Gidrazony [Hydrazones], Nauka, Moscow, 1974 (in Russian).

    Google Scholar 

  14. Ch. J. Abelt and J. M. Pleier,J. Am. Chem. Soc., 1989,111, 1795.

    Google Scholar 

  15. A. G. Mikhailovskii, B. B. Aleksandrov, and M. I. Vakhrin,Khim. Geterotsikl. Soedin., 1992, 1144 [Chem. Heterocycl. Compd., 1992 (Engl. Transl.)].

  16. M. Yu. Dormidontov, V. S. Shklyaev, and Yu. V. Shklyaev,Metalloorg. Khim., 1992,5, 1258 [Organomet. Chem. USSR, 1992, 5 (Engl. Transl.)].

    Google Scholar 

  17. M. J. S. Dewar,The Molecular Orbital Theory of Organic Chemistry, McGraw-Hill Book Company, New York, 1969.

    Google Scholar 

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Translated fromIzvestiya Akademii Nauk. Seriya Khimicheskaya, No. 12, pp. 2468–2474, December, 1995.

The authors are grateful to Professor V. F. Zakharov (Russian University of People's Friendship) for recording the1H NMR spectra.

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Sokol, V.I., Ryabov, M.A., Merkur'eva, N.Y. et al. Oxidation of 1-hydrazino-3,3-dimethyl-3,4-dihydroisoquinoline. X-ray, spectroscopic, and quantum-chemical study of the structure of 3,3-dimethyl-3,4-dihydroisocarbostyryl azine. Russ Chem Bull 44, 2364–2370 (1995). https://doi.org/10.1007/BF00713609

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  • DOI: https://doi.org/10.1007/BF00713609

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