Abstract
The recyclization in an acidic medium of enamino ketones that are imidazolidine derivatives leads to 1-pyrrolin-4-one 1-oxide derivatives, viz., cyclic Β-oxo nitrones, which exist in the form of equilibrium mixtures of the ene hydroxyamino keto and oxo nitrone tautomeric forms, the ratio of which depends on the solvent and the character of the substituent.
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Ya. F. Freimanis, The Chemistry of Enamino Ketones, Enamino Imines, and Enamino Thiones [in Russian], Zinatne, Riga (1974), p. 211.
G. Danhordt, Y. Geyer, K. K. Mayer, and R. Obergrusberger, Arc. Pharm., 321, 17 (1988).
V. A. Reznikov and L. B. Volodarskii, USSR Author's Certificate No. 1,356,400; Byull. Izobret., No. 24, 271 (1988).
S. A. Stekhova, O. A. Zagulyaeva, V. V. Lapachev, and V. P. Mamaev, Khim. Geterotsikl. Soedin., No. 6, 822 (1980).
V. V. Martin and L. B. Volodarskii, Izv. Akad. Nauk SSSR, Ser. Khim., No. 6, 1336 (1980).
D. St. C. Black, V. M. Clark, B. G. Odell, and A. Todd, J. Chem. Soc., Perkin Trans, 1, No.18, 1944 (1976).
F. De Sarlo and G. Renzi, J. Chem. Soc., Perkin Trans. 1, No. 10, 1113 (1978).
I. A. Grigor'ev, G. I. Shchukin, V. V. Martin, and V. I. Mamatyuk, Khim. Geterotsikl. Soedin., No. 2, 252 (1985).
V. V. Khramtsov, L. M. Weiner, S. I. Eremenko, O. I. Belchenko, P. V. Schastev, I. A. Grigor'ev, and V. A. Reznikov, J. Magn. Reson., 61, 397 (1985).
V. A. Reznikov, T. I. Reznikova, and L. B. Volodarskii, Zh. Org. Khim., 18, 2135 (1982).
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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 7, pp. 921–926, July, 1990.
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Reznikov, V.A., Volodarskii, L.B. Recyclization of enamino ketones that are imidazolidine derivatives to 1-pyrrolin-4-one 1-oxides. Chem Heterocycl Compd 26, 767–772 (1990). https://doi.org/10.1007/BF00509704
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DOI: https://doi.org/10.1007/BF00509704