TRANSFORMATIONS OF 1-[2-(ADAMANTAN-1-YL)-2-HYDROXYETHYL]-1,2,3,6-TETRAHYDROPYRIDINES BY THE ACTION OF TRIFLUOROMETHANESULFONIC ACID

Authors

  • Вера А. Шадрикова Samara State Technical University, 244 Molodogvardeyskaya St., Samara 443100
  • Евгений В. Головин Samara State Technical University, 244 Molodogvardeyskaya 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 Molodogvardeyskaya St., Samara 443100

DOI:

https://doi.org/10.1007/5761

Keywords:

adamantane derivatives, 1-azabicyclo[3.3.1]non-3-ene, homoadamantane, 1, 2, 3, 6-tetrahydropyridine, trifluoromethanesulfonic acid, carbocation, Wagner–Meerwein rearrangement

Abstract

1-[2-(Adamantan-1-yl)-2-hydroxyethyl]-1,2,3,6-tetrahydropyridines were obtained by reduction of 1-[(adamantan-1-yl)-2-oxoethyl]pyridinium bromides. By the action of trifluoromethanesulfonic acid, they undergo carbocationic intramolecular cyclization accompanied by the Wagner–Meerwein rearrangement with the formation of substituted 1-azabicyclo[3.3.1]non-3-enes annulated with the homoadamantane framework. The structure of the obtained compounds was confirmed by spectral methods and X-ray structural analysis.

Autthors: Vera А. Shadrikova*, Evgeny V. Golovin, Victor B. Rybakov, Yuri N. Klimochkin

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Published

2020-08-19

Issue

Vol. 56 No. 7 (2020): Synthesis and transformations of heterocycles under electrophilic conditions

Section

Original Papers