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Paper | Regular issue | Vol 63, No. 1, 2004, pp.63-74
Published online, 10th November, 2003
DOI: 10.3987/COM-03-9916
Preparation and Structure of Diexo-Oxanorbornane-fused 1,3-Heterocycles

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

*Institute of Pharmaceutical Chemistry, University of Szeged, H-6720 Szeged, Eötvös u. 6, Hungary


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 hetero-cycles 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 pyrimido-pyridazine 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.