Synthesis of Spiro Pyrrolidines From the Addition of Schiff Bases to -Arylidene Cyclohexanones

Abstract

A series of -arylidene cyclohexanones (1-4) had been prepared via Claisen-Schmidt condensation, while other series of N-arylidene benzylamines (Schiff bases 5-10) had also been synthesized by equimolar addition. The 1,3-anionic cycloaddition of Schiff bases to -arylidene cyclohexanones under basic conditions afforded the corresponding spiro pyrrolidines (11-23). The structures of the products are supported by valid spectral data and physical properties. Theoretical data had been used to support the suggested mechanism.