Syntheses of 2,3-dioxopyrrolidines with benzaldehyde using different amines / Nuhairi Alias

• Main Author: Alias, Nuhairi
• Format: Thesis
• Language: English
• Published: 2009
• Online Access: https://ir.uitm.edu.my/id/eprint/103662/1/103662.pdf; https://ir.uitm.edu.my/id/eprint/103662/

This thesis describes a simple and efficient methodology for the syntheses of 2,3-dioxopyrrolidine templates. 2,3-dioxopyrrolidine is a five-membered heterocyclic aromatic compound containing one nitrogen atom which can be found in certain natural products and is also incorporated in several pharmacologically active compounds. The procedure described in the thesis uses a one pot reaction whereby a three component reactants which are sodium diethyl oxalate, primary amines and aromatic aldehydes undergo a reaction all at once. Different primary amines and aldehydes are used which contribute to differences in percent yield. Formation of yellowish solids are depending on the reagents utilized. Two fundamental reactions involved in the synthesis are nucleophilic addition and Dieckmann cyclization to form the targeted compound. Each synthesized compounds are characterized using NMR and FTIR spectroscopic techniques to study the structure of the molecule. 2,3-dioxopyrrolidine is also attempted to undergo a reduction reaction using zinc powder in buffer solution of acetic acid and sulfuric acid. Unfortunately, the procedure has so far given only moderate yield but the results show that the principle works.