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SYNTHESIS OF ADAMANTYL-CONTAINING PHENYLPIPERIDINES

Вера А. Шадрикова, Евгений В. Головин, Вадим А. Ширяев, Марат Р. Баймуратов, Виктор Б. Рыбаков, Юрий Н. Климочкин
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Abstract


The reduction of quaternary 1-(adamantan-1-yl)pyridinium salts with sodium borohydride in ethanol gave 1-(adamantan-1-yl)-1,2,3,6-tetrahydropyridines that reacted with benzene in trifluoromethanesulfonic acid medium, leading to the formation of 1-(adamantan-1-yl)phenylpiperidines with various spatial orientation of the phenyl substituent. The structure of the obtained phenylpiperidines was confirmed by the spectral dataset. The thermodynamic stability calculations for the conformers of phenylpiperidines were performed with the B3LYP/6-311++(d,p) method.

How to Cite
Shadrikova, V. A.; Golovin, E. V.; Shiryaev, V. A.; Baimuratov, M. R.; Rybakov, V. B.; Klimochkin, Yu. N. Chem. Heterocycl. Compd. 2015, 51, 891. [Khim. Geterotsikl. Soedin. 2015, 51, 891.]

For this article in the English edition see DOI 10.1007/s10593-015-1792-4


Keywords


adamantane derivatives; phenylpiperidine; pyridinium salts; 1,2,3,6-tetrahydropyridine; conformer; DFT; hydroarylation; reduction

Full Text: PDF (Russian) Supplementary File(s): Supporting information (14MB)


 

 

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