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Synthesis of 1,4,6,10-tetraazaadamantane quaternary derivatives

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Abstract

Methods for the preparation of stable 1,4,6,10-tetraazaadamantane quaternary derivatives were developed based on quaternization of a tertiary nitrogen atom in tris(β-oximinoalkyl)amines or isomeric 4,6,10-trihydroxy-1,4,6,10-tetraazaadamantanes. This process constitutes a convenient approach to the introduction of a hydrophilic 1,4,6,10-tetraazaadamantane moiety into lipophilic molecules in order to increase their solubility in water. 4,6,10-Trihydroxy-1,4,6,10-tetraazaadamantane N-oxide was synthesized by the oxidation of the tertiary nitrogen atom in the tris-oxime and subsequent intramolecular cyclotrimerization of the oximino groups. Quantum chemical calculations showed that the quaternization of the annular nitrogen atom led to a considerable stabilization of tetraazaadamantane framework as compared to the open-chain form of tris-oxime.

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Authors and Affiliations

  1. N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky prosp., 119991, Moscow, Russian Federation

    A. N. Semakin, I. S. Golovanov, A. Yu. Sukhorukov, S. L. Ioffe & V. A. Tartakovsky

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  1. A. N. Semakin
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  2. I. S. Golovanov
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  3. A. Yu. Sukhorukov
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  4. S. L. Ioffe
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  5. V. A. Tartakovsky
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Correspondence to A. N. Semakin.

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Based on the materials of the International Congress on the Heterocyclic Chemistry "KOST-2015" (October 18—23, 2015, Moscow, Russia).

Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 9, pp. 2270—2277, September, 2016.

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Semakin, A.N., Golovanov, I.S., Sukhorukov, A.Y. et al. Synthesis of 1,4,6,10-tetraazaadamantane quaternary derivatives. Russ Chem Bull 65, 2270–2277 (2016). https://doi.org/10.1007/s11172-016-1577-7

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  • DOI: https://doi.org/10.1007/s11172-016-1577-7

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