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

Ferenc Miklós, P. Sohár, A. Csámpai, Reijo Sillanpää, Mária Péter, G. 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

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Isomerization
Carboxylic Acids
Heptanes
Cross-Linking Reagents
Putrescine
Nuclear magnetic resonance spectroscopy
Amines
Magnetic Resonance Spectroscopy

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

Isomerization and application of aroylnorbornene-carboxylic acids for stereoselective preparation of heterocycles. / Miklós, Ferenc; Sohár, P.; Csámpai, A.; Sillanpää, Reijo; Péter, Mária; Stájer, G.

In: Heterocycles, Vol. 57, No. 12, 01.12.2002, p. 2309-2320.

Research output: Contribution to journalArticle

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AB - 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.

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