SYNTHESIS OF ADAMANTYL-CONTAINING PHENYLPIPERIDINES

Authors

  • Вера А. Шадрикова Samara State Technical University, 244 Molodogvardeiskaya St., Samara 443100
  • Евгений В. Головин Samara State Technical University, 244 Molodogvardeiskaya St., Samara 443100
  • Вадим А. Ширяев Samara State Technical University, 244 Molodogvardeiskaya St., Samara 443100
  • Марат Р. Баймуратов Samara State Technical University, 244 Molodogvardeiskaya St., Samara 443100
  • Виктор Б. Рыбаков Lomonosov Moscow State University, 1, Build. 3 Leninskie Gory, Moscow 119991
  • Юрий Н. Климочкин Samara State Technical University, 244 Molodogvardeiskaya St., Samara 443100

DOI:

https://doi.org/10.1007/2637

Keywords:

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

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

Author Biographies

Вера А. Шадрикова, Samara State Technical University, 244 Molodogvardeiskaya St., Samara 443100

Вера Андреевна Шадрикова

Евгений В. Головин, Samara State Technical University, 244 Molodogvardeiskaya St., Samara 443100

Евгений Валерьевич Головин

Вадим А. Ширяев, Samara State Technical University, 244 Molodogvardeiskaya St., Samara 443100

Вадим Андреевич Ширяев

Марат Р. Баймуратов, Samara State Technical University, 244 Molodogvardeiskaya St., Samara 443100

Марат Рамильевич Баймуратов

Виктор Б. Рыбаков, Lomonosov Moscow State University, 1, Build. 3 Leninskie Gory, Moscow 119991

Виктор Борисович Рыбаков

Юрий Н. Климочкин, Samara State Technical University, 244 Molodogvardeiskaya St., Samara 443100

Юрий Николаевич Климочкин

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Published

2015-11-11

Issue

Vol. 51 No. 10 (2015)

Section

Original Papers