Synthesis of pyrrolidin-2-ylidenes and pyrrol-2-ylidenes via 1,3-dipolar cycloaddition of H-bond-assisted azomethine ylides to nitrostyrenes?
Organic & Biomolecular Chemistry Pub Date: 2023-05-31 DOI: 10.1039/D3OB00725A
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.
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Journal Name：Organic & Biomolecular Chemistry
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CAS no.: 89640-58-4
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