Synthesis of Spiropyrrolidines via 1, 3 Anionic Cycloaddition

Abdul Wahab J Al-Hamdany,Abdul Majeed M Dabbagh,Omar A Shareef

doi:10.33899/rjs.2012.59999

Abdul Wahab J Al-Hamdany, Abdul Majeed M Dabbagh + Show 1 more

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https://doi.org/10.33899/rjs.2012.59999

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Journal: Rafidain Journal of Science	Publication Date: Jul 1, 2012
Citations: 1	License type: cc-by

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.

Highlights

Spiro compounds having cyclic structure fused at a central carbon are of recent interest due to their interesting structural implications on biological system (Jayashankaran et al, 2005)
The most developed route for the synthesis of these compounds depends on the cycloaddition to an exocyclic bond. (Poornachandran and Raghunathan, 2010) (Fisera et al, 1994)
The 1,3-Anionic cycloaddition provides a way for the synthesis of many spiroheterocycles through the cycloaddition reaction of nonstabilised azomethine ylides with the Chalcones (Waldmann, 1995)

Summary

Introduction

Spiro compounds having cyclic structure fused at a central carbon are of recent interest due to their interesting structural implications on biological system (Jayashankaran et al, 2005). Highly substituted pyrrolidines have attracted much interest as they contribute the central structural element of many alkaloids and pharmacological active compounds (Luibineau et al, 1995) (Deshong and Leginus, 1983) (Manikandan et al, 2001) (Subramaniyan and Raghunathan, 2001) on the synthesis of novel spiropyrrolidinyl derivatives we have examined the 1,3-Anionic cycloaddition reaction of E-2-arylidene-1-tetralones with the azomethine ylide generated by treatment the Schiff bases with sodium hydroxide.

Results

Conclusion