Transformations of 1-[2-(Adamantan-1-Yl)-2-Hydroxyethyl]-1,2,3,6-Tetrahydropyridines by the Action of Trifluoromethanesulfonic Acid View Full Text


Ontology type: schema:ScholarlyArticle     


Article Info

DATE

2020-07

AUTHORS

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

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.

PAGES

898-908

References to SciGraph publications

  • 2015-10. Synthesis of adamantyl-containing phenylpiperidines in CHEMISTRY OF HETEROCYCLIC COMPOUNDS
  • 2017-11. The Ritter reaction for the synthesis of heterocycles in CHEMISTRY OF HETEROCYCLIC COMPOUNDS
  • 2017-03. Reactions of γ-sultones containing a polycyclic fragment in RUSSIAN JOURNAL OF ORGANIC CHEMISTRY
  • 2020-05-31. Structural Transformations of 2-(Adamantan-1-Yl)Aziridines in CHEMISTRY OF HETEROCYCLIC COMPOUNDS
  • 2016-10. Synthesis of substituted 1-[2-(adamantan-1-yl)ethyl]piperidines in RUSSIAN JOURNAL OF ORGANIC CHEMISTRY
  • 2003-07. Transformation of 1,2,5,6-Tetrahydropyridines with Mycellar Fungi in CHEMISTRY OF HETEROCYCLIC COMPOUNDS
  • 2015-06. Synthesis of γ-sultones based on conversion of adamantane-type olefins in CHEMISTRY OF HETEROCYCLIC COMPOUNDS
  • 2015-01-06. Adamantylation of Pyridine Derivatives in CHEMISTRY OF HETEROCYCLIC COMPOUNDS
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    DOI

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