Synthesis and structural determination of pyrrolidine-2,3-dione derivatives from 4-acetyl-3-hydroxy-5-phenyl-1-(3-nitrophenyl)-3-pyrroline-2-one

Abstract

Numerous heterocyclic compounds containing 3-pyrroline-2-one or pyrrolidine-2,3-dione core have been found in nature and showed valuable biological activities. Therefore, the synthesis of 3-pyrroline-2-one derivatives and pyrrolidine-2,3-dione derivatives have attracted more and more attention from organic chemists and medicinal chemists. In this manuscript, 4-acetyl-3-hydroxy-1-(3-nitrophenyl)-5-phenyl-3-pyrroline-2-one has been prepared via three-component reaction and, besides, two 1,4,5-trisubstituted pyrrolidine-2,3-diones have also been synthesized via the reaction between the above 3-pyrroline-2-one derivative and aliphatic amine such as methylamine and 4-methoxybenzylamine. The structure of desired products have been confirmed via 1D NMR (1H NMR, 13C NMR), 2D NMR (HSQC, HMBC) and high resolution mass spectrometry (ESI – HRMS).

Keywords

• 2-pyrrolidinone
• 3-pyrrolin-2-one
• 1,4,5-trisubstituted pyrrolidine-2,3-dione
• 1,5-dihydro-2h-pyrrol-2-one
• multi-component reaction