1,3-dipolar cycloaddition as a method for the synthesis of dipyrrolidinyl- and dipyrrolylketones

In the reactions of 1,3-dipolar cycloaddition of a twofold excess of aryl aldimines of glycine ethyl ester with diarylideneacetones and diarylidenecyclohexanones in the presence of silver acetate, the corresponding dipyrrolidinylketones were obtained. Diethyl 4,4′-carbonylbis(3,5-diarylpyrrolidine-2-carboxylates) obtained from diarylideneacetones undergo aromatization under the action of N-bromosuccinimide to form diethyl 4,4′-carbonylbis(3,5-diaryl-1H-pyrrole-2-carboxylates). The selectivity of the reactions and the structure of the products were determined using correlation NMR spectroscopy and X-ray diffraction analysis.