Synthesis of Spiropyrrolidines via 1, 3 Anionic Cycloaddition

Abstract

In this work, series of substituted α, β-unsaturated carbonyl compounds (A1-8) had been prepared using Claisen-Schmidt condensation. Also, series of substituted Schiff bases (N-arylidene-4-picolyamine) (B1-6) were prepared by the condensation of 4-picolyamine with various aromatic aldehydes. The reaction of the above mentioned materials (A+B) afforded the desired products [Spiropyrrolidines (S1-15)]. The reaction occurred through the formation of azallyl anion which acted as a nucleophile that has the ability to attack the exocylic double bond of chalcones through the 1,3-anionic cycloaddition mechanism to form the product. The structure for all synthesized compounds (chalcones, Schiff bases, pyrrolidines) had been confirmed by the spectral data obtained by (UV, IR, 1H-NMR) as well as the determination of physical properties.