2,4,9‐Triazaadamantanes with “Clickable” Groups: Synthesis, Structure and Applications as Tripodal Platforms

2,4,9‐Triazaadamantanes with “Clickable” Groups: Synthesis, Structure and Applications as Tripodal Platforms Full article

Journal

European Journal of Organic Chemistry
ISSN: 1434-193X , E-ISSN: 1099-0690

Output data

Year: 2020, Volume: 2020, Number: 43, Pages: 6723-6735 Pages count : 13 DOI: 10.1002/ejoc.202000832

Authors

Semakin Artem N. ¹ , Nelyubina Yulia V. ² , Ioffe Sema L. ¹ , Sukhorukov Alexey Yu. ^1,3

Affiliations

1	Laboratory of organic and metal-organic nitrogen-oxygen systems N. D. Zelinsky Institute of Organic Chemistry Leninsky prospect, 47 119991 Moscow Russia
2	Center for molecular composition studies A. N. Nesmeyanov Institute of Organoelement Compounds Vavilov str. 28 119991 Moscow Russia
3	Department of Innovational Materials and Technologies Chemistry, Plekhanov Russian University of Economics, Stremyanny per. 36, 117997 Moscow, Russia

2,4,9-Triazaadamantanes (TRIADs) are promising yet scarcely available, conformationally rigid platforms for potential applications in the design of functional molecules and materials. Here, we report a facile synthesis of various N- and C7-substituted 2,4,9-triazaadamantanes, starting from amines and 4-allylhepta-1,6-dienes. A focus was placed on the synthesis of 2,4,9-triazaadamantanes bearing reactive groups (NH2, propargyl, OH) on the bridge nitrogen atoms, which were then used to decorate the 3D scaffold by hydrazone, triazole, and boronate linkages. A reversible opening of the adamantane cage to the acyclic tris-oxime form was observed for 2,4,9-triazaadamantanes possessing hydroxy-groups on the nitrogen atoms (TRIAD-triols). This process could be controlled by temperature or by complexation of TRIAD-triol with a boronic acid. The structure of 2,4,9-triazaadamantanes and the stereodynamics at the bridge nitrogen atoms were studied by X-ray analysis and DFT calculations.

Semakin A.N. , Nelyubina Y.V. , Ioffe S.L. , Sukhorukov A.Y.
2,4,9‐Triazaadamantanes with “Clickable” Groups: Synthesis, Structure and Applications as Tripodal Platforms
European Journal of Organic Chemistry. 2020. V.2020. N43. P.6723-6735. DOI: 10.1002/ejoc.202000832 WOS Scopus OpenAlex

Web of science:	WOS:000560051300001
Scopus:	2-s2.0-85089467057
OpenAlex:	W3045911461

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