Synthesis of pyrrolidin-2-ylidenes and pyrrol-2-ylidenes via 1,3-dipolar cycloaddition of H-bond-assisted azomethine ylides to nitrostyrenes

Abstract

Hydrogen-bond-assisted azomethine ylides, generated from 2-(benzylamino)-2-(1,3-dioxo-1,3-dihydro-2H-inden-2-ylidene)acetonitriles, undergo a formal Huisgen 1,3-dipolar cycloaddition with β-bromo-β-nitrostyrenes to afford a diastereoselective synthesis of highly substituted pyrrolidin-2-ylidene derivatives. When β-nitrostyrenes were used as the alkene component, 2-(4,5-diaryl-1,5-dihydro-2H-pyrrol-2-ylidene)-1H-indene-1,3(2H)-diones were obtained. Efficient conversion of pyrrolidene-2-ylidenes to the corresponding pyrrol-2-ylidenes takes place in refluxing 1-propanol in the presence of excess Et₃N. Also, the structure of the pyrrolidene-2-ylidene derivative was determined by X-ray crystallography.