Synthesis of azolyl-substituted adamantane derivatives and their coordination compounds
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1953
Synthesis of azolyl-substituted adamantane derivatives and their coordination compounds D. I. Pavlov,а T. S. Sukhikh,b,c and A. S. Potapovb aNational
Research Tomsk Polytechnic University, 30 prosp. Lenina, 634050 Tomsk, Russian Federation bNikolaev Institute of Inorganic Chemistry, Siberian Branch of the Russian Academy of Sciences, 3 prosp. Akad. Lavrentieva, 630090 Novosibirsk, Russian Federation. Fax: +7 (383) 330 9489. E-mail: [email protected] cNovosibirsk State University, 1 ul. Pirogova, 630090 Novosibirsk, Russian Federation Reactions of adamantylazoles with nucleophiles (water, carbon monoxide, acetonitrile) in sulfuric acid were studied. New bifunctional adamantane derivatives containing one heterocyclic substituent and one hydroxyl or acetamide substituent were synthesized. The coordination compounds of copper(II) and zinc(II) with 1-adamantyl-1,2,4-triazole, 4-adamantylpyrazole, and 4-adamantyl-3,5-dimethylpyrazole were synthesized and structurally characterized. These complexes are first examples of coordination compounds of azolyladamantanes. Key words: adamantane, triazole, pyrazole, zinc, copper, coordination compounds, X-ray diffraction.
Since the discovery of antiviral activity of amantadine, a great diversity of molecules containing an adamantyl moiety were synthesized. 1—5 N-Adamantylazoles are a specific class of compounds, which have attracted attention due to their potential biological activity. In particular, adamantylpyrazoles were comprehensively investigated, mainly by Elguero´s research team.6—10 Despite the fact that the structures of adamantylazoles and their biological activity were studied in sufficient detail,11 data on the possibility of further functionalization of the adamantane skeleton in adamantylazoles are scarce in the literature. Meanwhile, adamantane is a very popular molecular platform for the construction of rigid non-aromatic ligands, which are used in the synthesis of thermally stable metal organic frameworks (MOFs).12—15 Most coordination compounds with azoles containing an adamantane moiety belong to transition metal carbene complexes, with 1,3-diadamantylimidazole being their precursor. On the contrary, only a few compounds are known in which monoazolyladamantane is coordinated to a metal ion via donor nitrogen atoms. Thus, a series of coordination compounds of cadmium(II) with 4-(1-adamantyl)-1,2,4triazole and various counterions were synthesized in the study.16 In all these compounds, the ligands serve as bridges and are coordinated via nitrogen atoms of 1,2,4-triazole rings at the 1 and 2 positions. In the anionic ruthenium(III) complex with 1-adamantylimidazole, which has recently been synthesized and structurally characterized,17 this ligand is coordinated via the nitrogen atom at the 3 posi-
tion of the imidazole ring, and the octahedral coordination environment of ruthenium(III) is completed by four chloride ions in the equatorial plane and a DMSO molecule. Since unsymmetrically substituted adamantanes bearing a heterocyclic moiety are of interest as
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