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Adduct of dimedone and 1,1,2-tribenzoylethylene. Keto-enol tautomerism and reactions with N-nucleophiles

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Abstract

Condensation of dimedone with 1,1,2-tribenzoylethylene provided pentaketone, where the position of the keto-enol equilibrium in the dibenzoylmethane fragment depended on external factors. In reactions with N-nucleophiles the pentaketone behaves as 1,4-diketone, affording with ammonium acetate, methylamine, and hydroxylamine hydrochloride functional derivatives of 4,5,6,7-tetrahydroindole, and with hydrazine hydrate, a pyridazine derivative.

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Correspondence to A. N. Andin.

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Original Russian Text © A.V. Andina, A.N. Andin, 2015, published in Zhurnal Organicheskoi Khimii, 2015, Vol. 51, No. 2, pp. 226–228.

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Andina, A.V., Andin, A.N. Adduct of dimedone and 1,1,2-tribenzoylethylene. Keto-enol tautomerism and reactions with N-nucleophiles. Russ J Org Chem 51, 214–216 (2015). https://doi.org/10.1134/S107042801502013X

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  • DOI: https://doi.org/10.1134/S107042801502013X

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