Synthesis of 1,4,6,10-tetraazaadamantane quaternary derivatives
- 作者: Semakin A.1, Golovanov I.1, Sukhorukov A.1, Ioffe S.1, Tartakovsky V.1
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隶属关系:
- N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences
- 期: 卷 65, 编号 9 (2016)
- 页面: 2270-2277
- 栏目: Full Articles
- URL: https://journals.rcsi.science/1066-5285/article/view/238982
- DOI: https://doi.org/10.1007/s11172-016-1577-7
- ID: 238982
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详细
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.
作者简介
A. Semakin
N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences
编辑信件的主要联系方式.
Email: sukhorukov@ioc.ac.ru
俄罗斯联邦, 47 Leninsky prosp., Moscow, 119991
I. Golovanov
N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences
Email: sukhorukov@ioc.ac.ru
俄罗斯联邦, 47 Leninsky prosp., Moscow, 119991
A. Sukhorukov
N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences
Email: sukhorukov@ioc.ac.ru
俄罗斯联邦, 47 Leninsky prosp., Moscow, 119991
S. Ioffe
N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences
Email: sukhorukov@ioc.ac.ru
俄罗斯联邦, 47 Leninsky prosp., Moscow, 119991
V. Tartakovsky
N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences
Email: sukhorukov@ioc.ac.ru
俄罗斯联邦, 47 Leninsky prosp., Moscow, 119991