Abstract
4-Aminoethylidene and 4-aminomethylene derivatives of 5-imidazolone exist in the enamine form as two isomers that are stabilized by intramolecular hydrogen bonds of the NH⋯N and NH⋯O type. In solution the enamine with a five-membered H ring is gradually converted to the corresponding isomer with a six-membered H ring with an NH⋯O bond. Because of steric hindrance, rotation about the carbon-carbon double bond is realized more slowly in the aminoethylidene derivatives than in the aminomethylene derivatives of 5-imidazolone.
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See [1] for communication XXI.
Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 12, pp. 1677–1679, December, 1978.
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Kvitko, I.Y., Kurkovskaya, L.N., Khozeeva, R.V. et al. Aminomethylene derivatives of azoles. Chem Heterocycl Compd 14, 1364–1366 (1978). https://doi.org/10.1007/BF00487408
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DOI: https://doi.org/10.1007/BF00487408