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Synthesis of Bisacridine Derivatives with Pyridine and 1,2-Azole Fragments

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Abstract

A convenient one-step method for the synthesis of new bisacridine derivatives, containing fragments of 5-arylisoxazoles, 4,5-dichloroisothiazole, as well as isonicotinic acid residues covalently attached by ester groups to various positions of the aromatic core, was developed. A three-component cascade condensation of 1,5-naphthalenediamine, aldehydes, and cyclic β-dicarbonyl compounds was carried out by refluxing in butanol. Quaternary ammonium salts of synthesized bisacridine derivatives were obtained. It was shown that the synthesized bisacridine compounds form complexes with palladium LPdCl2, which exhibit high catalytic activity in the model Suzuki reaction in water in the absence of organic co-solvent.

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Funding

This work was supported in part by the Russian Foundation for Basic Research (grant no. 20-58-00005-Bel_a) and the Belarusian Republican Foundation for Basic Research (grant X20R-017).

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Authors and Affiliations

  1. Institute of Physical Organic Chemistry, National Academy of Sciences of Belarus, 220072, Minsk, Belarus

    E. A. Dikusar, E. A. Akishina, S. K. Petkevich, N. A. Zhukouskaya, L. N. Filippovich & V. I. Potkin

  2. Lomonosov Moscow State University, Chemical Department, 119991, Moscow, Russia

    R. S. Alekseyev & N. A. Bumagin

  3. Institute of Chemistry of New Materials, National Academy of Sciences of Belarus, 220141, Minsk, Belarus

    S. N. Shahab

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  1. E. A. Dikusar
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  4. N. A. Zhukouskaya
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  5. R. S. Alekseyev
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Correspondence to E. A. Dikusar.

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Dikusar, E.A., Akishina, E.A., Petkevich, S.K. et al. Synthesis of Bisacridine Derivatives with Pyridine and 1,2-Azole Fragments. Russ J Gen Chem 92, 40–53 (2022). https://doi.org/10.1134/S1070363222010078

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  • DOI: https://doi.org/10.1134/S1070363222010078

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