Synthesis of 1,4,6,10-tetraazaadamantane quaternary derivatives
- Authors: Semakin A.N.1, Golovanov I.S.1, Sukhorukov A.Y.1, Ioffe S.L.1, Tartakovsky V.A.1
-
Affiliations:
- N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences
- Issue: Vol 65, No 9 (2016)
- Pages: 2270-2277
- Section: Full Articles
- URL: https://journals.rcsi.science/1066-5285/article/view/238982
- DOI: https://doi.org/10.1007/s11172-016-1577-7
- ID: 238982
Cite item
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.
About the authors
A. N. Semakin
N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences
Author for correspondence.
Email: sukhorukov@ioc.ac.ru
Russian Federation, 47 Leninsky prosp., Moscow, 119991
I. S. Golovanov
N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences
Email: sukhorukov@ioc.ac.ru
Russian Federation, 47 Leninsky prosp., Moscow, 119991
A. Yu. Sukhorukov
N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences
Email: sukhorukov@ioc.ac.ru
Russian Federation, 47 Leninsky prosp., Moscow, 119991
S. L. Ioffe
N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences
Email: sukhorukov@ioc.ac.ru
Russian Federation, 47 Leninsky prosp., Moscow, 119991
V. A. Tartakovsky
N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences
Email: sukhorukov@ioc.ac.ru
Russian Federation, 47 Leninsky prosp., Moscow, 119991