Intramolecular cyclization with oxocarbeniumion. Synthesis of 1-azabicyclo[3.3.1]nonene and [3.2.1]octene derivatives

Sándor Sólyom, Gizella Ábrahám, Márta Szöllõsy, István Pallagi, Emese Csuzdi, István Ling, Beáta Vitális, Katalin Horváth, Edit J. Horváth, L. Hársing, Judit Kajtár

Research output: Contribution to journalArticle

6 Citations (Scopus)

Abstract

Hydroxy- and aryl-substituted 1-azabicyclo[3.3.1]nonene and [3.2.1]octene derivatives have been synthesized by the intramolecular cationic cyclization of 4-aryl-1,2,5,6-tetrahydropyridines bearing an acetal moiety in the nitrogen substituent. Factors governing the stereoselectivity of the ring closure step have been disclosed. Two compounds were resolved into the enantiomers and the absolute configuration of one of them was deduced from CD investigations. Among the new compounds substances with valuable antiamnesic effect have been found.

Original languageEnglish
Pages (from-to)1139-1168
Number of pages30
JournalHeterocycles
Volume41
Issue number6
Publication statusPublished - Jun 1 1995

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Bearings (structural)
Stereoselectivity
Acetals
Enantiomers
Cyclization
Nitrogen
Derivatives

ASJC Scopus subject areas

  • Pharmacology
  • Organic Chemistry
  • Analytical Chemistry

Cite this

Sólyom, S., Ábrahám, G., Szöllõsy, M., Pallagi, I., Csuzdi, E., Ling, I., ... Kajtár, J. (1995). Intramolecular cyclization with oxocarbeniumion. Synthesis of 1-azabicyclo[3.3.1]nonene and [3.2.1]octene derivatives. Heterocycles, 41(6), 1139-1168.

Intramolecular cyclization with oxocarbeniumion. Synthesis of 1-azabicyclo[3.3.1]nonene and [3.2.1]octene derivatives. / Sólyom, Sándor; Ábrahám, Gizella; Szöllõsy, Márta; Pallagi, István; Csuzdi, Emese; Ling, István; Vitális, Beáta; Horváth, Katalin; Horváth, Edit J.; Hársing, L.; Kajtár, Judit.

In: Heterocycles, Vol. 41, No. 6, 01.06.1995, p. 1139-1168.

Research output: Contribution to journalArticle

Sólyom, S, Ábrahám, G, Szöllõsy, M, Pallagi, I, Csuzdi, E, Ling, I, Vitális, B, Horváth, K, Horváth, EJ, Hársing, L & Kajtár, J 1995, 'Intramolecular cyclization with oxocarbeniumion. Synthesis of 1-azabicyclo[3.3.1]nonene and [3.2.1]octene derivatives', Heterocycles, vol. 41, no. 6, pp. 1139-1168.
Sólyom S, Ábrahám G, Szöllõsy M, Pallagi I, Csuzdi E, Ling I et al. Intramolecular cyclization with oxocarbeniumion. Synthesis of 1-azabicyclo[3.3.1]nonene and [3.2.1]octene derivatives. Heterocycles. 1995 Jun 1;41(6):1139-1168.
Sólyom, Sándor ; Ábrahám, Gizella ; Szöllõsy, Márta ; Pallagi, István ; Csuzdi, Emese ; Ling, István ; Vitális, Beáta ; Horváth, Katalin ; Horváth, Edit J. ; Hársing, L. ; Kajtár, Judit. / Intramolecular cyclization with oxocarbeniumion. Synthesis of 1-azabicyclo[3.3.1]nonene and [3.2.1]octene derivatives. In: Heterocycles. 1995 ; Vol. 41, No. 6. pp. 1139-1168.
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