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

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

Journal

Russian Chemical Bulletin
ISSN: 1573-9171 , E-ISSN: 1066-5285

Output data

Year: 2016, Volume: 65, Number: 9, Pages: 2270-2277 Pages count : 8 DOI: 10.1007/s11172-016-1577-7

Authors

Semakin A.N. ¹ , Golovanov I.S. ¹ , Sukhorukov A.Yu. ¹ , Ioffe S.L. ¹ , Tartakovsky V.A. ¹

Affiliations

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

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.

Semakin A.N. , Golovanov I.S. , Sukhorukov A.Y. , Ioffe S.L. , Tartakovsky V.A.
Synthesis of 1,4,6,10-tetraazaadamantane quaternary derivatives
Russian Chemical Bulletin. 2016. V.65. N9. P.2270-2277. DOI: 10.1007/s11172-016-1577-7 WOS Scopus OpenAlex

Web of science:	WOS:000400400700019
Scopus:	2-s2.0-85019045063
OpenAlex:	W2608759231

DB	Citing
OpenAlex	5
Scopus	6
Web of science	5