Abstract
1-Phenyl-cyclopenteno[1,2-d]-1,2,3-rriazolo-5-spiro-4′-[perhydropyrazolino-3′,5′-dione] (5) afforded in situ, by oxidation with lead tetraacetate, the corresponding cyclopentenotriazolo-spiropyrazolodione 6, which was trapped with dienes giving the hetero-Diels-Alder adducts 10–12 in good yields. The Diels-Alder reactions were examined on the basis of AM1 MO calculations. Total assignment of the 1H- and 13C-nmr chemical shifts as well as the relative configuration of these adducts was accomplished with the help of 2D (1H-1H COSY, 1H-1H NOESY, 1H-13C XHCORR, 1H-13C COLOC) and NOE difference spectroscopy. The structures of compounds 11a and 11b were also examined by molecular modeling.
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