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■ Transformation of Oxomethanobenzocyclooctenecarboxylic Acids to Pyrrolidinone-fused Penta-, Hexa- and Heptacyclic Hetero Compounds

Ferenc Miklós, Géza Stájer,* Pál Sohár, Gábor Bernáth, and Reijo Sillanpää

*Institute of Pharmaceutical Chemistry, Albert Szent-Györgyi Medical University, POB 121, H-6701 Szeged, Eötvös u. 6, Hungary

Abstract

10-Oxo-5r,6,7,8c,9c,10-hexahydro-5,9-methanobenzocyclooctene-8-carboxylic acid (1a) or a C-8 epimeric mixture (1a and 1b) reacted with 1,2-, 1,3- and 1,4-bifunctional reagents, 1,2- or 1,3-diaminopropane (2, 3), 1,2- or 1,3-propanolamine (4, 5), 1,4-diaminobutane (6), o-aminothiophenol (7), diexo-3-aminobicyclo[2.2.1]heptane-2-methanol or diendo-3-aminobicyclo[2.2.1]hept-5-ene-2-methanol (8, 9), to produce polycyclic compounds containing a pyrrolo-condensed pyrimidine (10), imidazole (11), 1,3-oxazine (12, 16, 17), oxazole (13), 1,3-diazepine (14), benzthiazole (15) moiety and one or two terminal aromatic rings by cyclization. The structures of 10-17 were established by ¹H and ¹³C NMR spectroscopy and for 16 also by X-Ray analysis.