Isomerization and application of aroylnorbornene-carboxylic acids for stereoselective preparation of heterocycles

Ferenc Miklós, Pál Sohár, Antal Csámpai, Reijo Sillanpää, Mária Péter, Géza Stájer

Research output: Contribution to journalArticle

11 Citations (Scopus)

Abstract

When boiled in acidic or basic solution, diendo-3-aroylbicyclo[2.2.1]heptane-2-carboxylic acids (1 and 1a) isomerize to exo-3-aroylbicyclo[2.2.1]heptane-endo-2-carboxylic acids (2 and 2a). Similar endo→exo and even exo→endo isomerization of the aroyl group occurred when the Diels-Alder product containing a mixture of 3-exo-p-toluoylbicyclo[2.2.1]hept-5-ene-2-endo-carboxylic acid (4) and 3-endo-p-toluoylbicyclo[2.2.1]hept-5-ene-2-exo-carboxylic acid (5) was reacted with bifunctional reagents: o-aminothiophenol, 3-amino-1-propanol, 1,4-diaminobutane or diexo-3-hydroxymethylbicyclo[2.2.1]heptane-2-amine. All the reactions yielded mixtures of norbomene diendo- and diexo-fused heterocycles (6) and (7, 8 and 10, 9 and 11, or 12 and 13), which were separated and whose structures were established by means of IR, 1H- and 13C-NMR spectroscopy, with DIFFNOE, 2D-COSY, DEPT, HMQC and HMBC measurements.

Original languageEnglish
Pages (from-to)2309-2320
Number of pages12
JournalHeterocycles
Volume57
Issue number12
Publication statusPublished - Dec 1 2002

ASJC Scopus subject areas

  • Analytical Chemistry
  • Pharmacology
  • Organic Chemistry

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