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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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.)].
M. Tishler and B. Stanovnik,Khim. Geterotsikl. Soedin., 1980, 579 [Chem. Heterocycl. Compd., 1980 (Engl. Transl.)].
E. M. Gizatullina and V. G. Kartsev,Khim. Geterotsikl. Soedin., 1993, 1587 [Chem. Heterocycl. Compd., 1993 (Engl. Transl.)].
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.)].
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.)].
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.)].
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.)].
L. J. Bellamy,The Infra-red Spectra of Complex Molecules, J. Wiley and Sons, Inc., New York, London, 1954.
A. V. Johansen, inVodorodnaya svyaz' [The Hydrogen Bond], Ed. N. D. Sokolov, Nauka, Moscow, 1981, 134 (in Russian).
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.)].
B. Yoshio, E. Osamu, and T. Masanao,Chem. Pharm. Bull., 1960,8, 194.
O. V. Sverdlova,Elektronnye spektry v organicheskoi khimii [Electronic Spectra in Organic Chemistry], Khimiya, Leningrad, 1985 (in Russian).
Yu. P. Kitaev and B. I. Buzykin,Gidrazony [Hydrazones], Nauka, Moscow, 1974 (in Russian).
Ch. J. Abelt and J. M. Pleier,J. Am. Chem. Soc., 1989,111, 1795.
A. G. Mikhailovskii, B. B. Aleksandrov, and M. I. Vakhrin,Khim. Geterotsikl. Soedin., 1992, 1144 [Chem. Heterocycl. Compd., 1992 (Engl. Transl.)].
M. Yu. Dormidontov, V. S. Shklyaev, and Yu. V. Shklyaev,Metalloorg. Khim., 1992,5, 1258 [Organomet. Chem. USSR, 1992, 5 (Engl. Transl.)].
M. J. S. Dewar,The Molecular Orbital Theory of Organic Chemistry, McGraw-Hill Book Company, New York, 1969.
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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