Research ArticlesStructure and Synthesis of 2-(4′-Substituted Phenyl)-Δ1-pyrrolines from 4-Phthalimidobutyryl Chloride via Friedel-Crafts Acylation

Add time:09/24/2019    Source:sciencedirect.com

2-(4′-Substituted phenyl)-Δ1-pyrrolines can be prepared conveniently from the hydrochlorides of 4′-substituted-4-aminobutyrophenones or their cyclization products, the corresponding Δ1-pyrrolines hydrochlorides, by alkalinization. The hydrochlorides were prepared by the hydrolyses of 4′-substituted-4-phthalimidobutyrophenones, which were obtained from the Friedel-Crafts acylation reaction between the substituted benzenes and γ-phthalimidobutyryl chloride. Spectral evidence indicates that all the products obtained are Δ1-pyrrolines rather than the Δ2-isomers. This method should provide easy access to those 2-(4′-substituted phenyl)-Δ1-pyrrolines unavailable by other routes due to the unavailability of the corresponding β-cyano and γ-nitro ketone intermediates or the corresponding Grignard reagents.

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