Preparation and structure of diexo-oxanorbornane-fused 1,3-heterocycles

Ferenc Miklós, Iván Kanizsai, Steffen Thomas, Erich Kleinpeter, Reijo Sillanpää, Géza Stájer

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15 Citations (Scopus)

Abstract

Via the reaction of diexo-oxanorbornanedicarboxylic anhydride with toluene, the diexo-aroylcarboxylic acid (3a) was prepared, which exists partly as the tautomeric lactol (3b). With bifunctional reagents, 3a yields fused heterocycles containing three-six rings. Thus, alkylenediamines result in imidazole- and 1,3-diazepine-fused oxygen-bridged isoindolones (6a,b), alkanolamines form the oxazole- and 1,3-oxazine-fused oxanorbornene derivatives (7a-c), and o-phenylenediamine undergoes cyclization to furnish the condensed benzimidazole (8). The reaction of 3a with diexo-aminonorbornanecarbohydrazide yields a pyrimidopyridazine containing six condensed rings (9). In a similar reaction with diendo-aminonorbornenecarbohydrazide, cyclopentadiene cleaves off to give the tricyclic retro Diels-Alder product (10). The structures, and particulary the configurations at the oxanorbornane ring systems and the position of the aryl substituent, were established by means of 1D- and 2D-NMR spectroscopy and, for 3b and 7c, also by X-Ray measurements.

Original languageEnglish
Pages (from-to)63-74
Number of pages12
JournalHeterocycles
Volume63
Issue number1
Publication statusPublished - Jan 1 2004

ASJC Scopus subject areas

  • Analytical Chemistry
  • Pharmacology
  • Organic Chemistry

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    Miklós, F., Kanizsai, I., Thomas, S., Kleinpeter, E., Sillanpää, R., & Stájer, G. (2004). Preparation and structure of diexo-oxanorbornane-fused 1,3-heterocycles. Heterocycles, 63(1), 63-74.