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Protonation of Anionic σ-Complexes of 5,7-Dinitroquinolin-8-ol

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Abstract

The reaction of 5,7-dinitroquinolin-8-ol with NaBH4 produces a reactive hydride σ-complex, the treatment of which with a solution of acetic acid gives 5,7-dinitro-5,6-dihydroquinolin-8-ol. The protonation of the acetone σ-complex of 5,7-dinitroquinolin-8-ol forms a mixture of the tautomers 5,7-dinitro-6-(2-oxopropyl)-6,7-dihydroquinoline-8(5H)-one and 5,7-dinitro-5,6-dihydro-6-(2-oxopropyl)quinolin-8-ol, with a predominance of the latter.

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Authors and Affiliations

  1. Lev Tolstoi Tula State Pedagogical University, 300026, Tula, Russia

    I. I. Ustinov, N. V. Khlytin, I. V. Shahkeldyan & Yu. M. Atroshchenko

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  1. I. I. Ustinov
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  2. N. V. Khlytin
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  3. I. V. Shahkeldyan
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  4. Yu. M. Atroshchenko
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Ustinov, I.I., Khlytin, N.V., Shahkeldyan, I.V. et al. Protonation of Anionic σ-Complexes of 5,7-Dinitroquinolin-8-ol. Russ J Org Chem 56, 2039–2042 (2020). https://doi.org/10.1134/S1070428020110214

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