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A Reaction of Berberine with Amides in Alkaline Media: An Experimental and Quantum-Chemical Study

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Chemistry of Heterocyclic Compounds Aims and scope

The possibility of obtaining electroneutral 8-amido derivatives of dihydroberberines was shown experimentally and with the support of quantum-chemical calculations based on the density functional theory (B3LYP/6-311+G(d,p)). In alkaline media, amides deprotonated to form amide anions, which, in turn, could add to the berberine framework at the C-8 position. Competing processes in this case were the reactions of the formation of 8-hydroxy- or 8-alkoxyberberines.

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Authors and Affiliations

  1. Department of Chemistry, Southern Federal University, 7 Zorge St., Rostov-on-Don, 344090, Russia

    Alexander D. Zagrebaev, Oleg N. Burov, Mikhail E. Kletskii & Sergey V. Kurbatov

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  1. Alexander D. Zagrebaev
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  2. Oleg N. Burov
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  3. Mikhail E. Kletskii
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  4. Sergey V. Kurbatov
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Correspondence to Oleg N. Burov.

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Translated from Khimiya Geterotsiklicheskikh Soedinenii, 2022, 58(6/7), 363–367

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Zagrebaev, A.D., Burov, O.N., Kletskii, M.E. et al. A Reaction of Berberine with Amides in Alkaline Media: An Experimental and Quantum-Chemical Study. Chem Heterocycl Comp 58, 363–367 (2022). https://doi.org/10.1007/s10593-022-03099-2

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