Synthesis, Molecular and Crystal Structures of Polyfluoroaryl-Substituted Aminodiaza- and Aminotriazadamantanes

E.N.Kudryavtseva^a, A.V.Medved′ko^a, A.D.Arutyunyan^b, K.A.Gevorkyan^b, M.V.Galstyan^b, S.P.Gasparyan^b, S.Z.Vatsadze^a, G.V.Romanenko^c, *, A.A.Korlyukov^d, and E.V.Tretyakov^a, **

^aZelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russia

^bScientific Technological Center of Organic and Pharmaceutical Chemistry of the National Academy of Sciences of the Republic of Armenia, Yerevan, Armenia

^cInternational Tomography Center, Siberian Branch, Russian Academy of Sciences, Novosibirsk, Russia

^dNesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, Moscow, Russia

email: *romanenko@tomo.nsc.ru
email: **tretyakov@ioc.ac.ru

Received 15 October, 2024

Abstract— 4-((5,7-Dimethyl-1,3-diazaadamantan-6-yl)amino)-2,3,5,6-tetrafluorobenzonitrile, 5,7-dimethyl-N-(2,3,5,6-tetrafluoro-4-nitrophenyl)-1,3-diazaadamantane-6-amine, 4-((1,3,5-triaza-adamantan-7-yl)amino)-2,3,5,6-tetrafluorobenzonitrile, and N-(2,3,5,6-tetrafluoro-4-nitrophenyl)-1,3,5-triaza-adamantane-7-amine are prepared by the interaction of 5,7-dimethyl-1,3-diazaadamantane-6-amine or 1,3,5-triazaadamantane-7-amine with the corresponding polyfluorinated aromatic compound (perfluorobenzonitrile or perfluoronitrobenzene). All the compounds are structurally characterized by NMR and IR spectroscopy, high-resolution mass spectrometry, and XRD. The structures of triazaadamantane derivatives, in contrast to substituted diazaadamantanes, contain multiple short F⋯F contacts.

Keywords: polyfluoroarenes, aromatic nucleophilic substitution, anilines, azaadamantanes.

DOI: 10.1134/S0022476625020118