Synthesis and structural determination of some 1,5-disubstituted-4-ethoxycarbonyl-3-hydroxy-3-pyrroline-2-one derivatives containing nitro group

Abstract

2-Pyrrolidinone is a γ-lactam heterocycle consisting of four carbon atoms and one nitrogen atom. In the family of 2-pyrrolidinone heterocycles, 3-pyrroline-2-ones, also named as 1,5-dihydro-2H-pyrrol-2-ones are important substructures of various natural products with promising biological activities. In addition, this γ-lactam heterocyclic ring also exists in synthetic medicinal compounds. In this manuscript, multi-component reactions (MCRs) were applied to synthesize three 1,5-disubstituted-4-ethoxycarbonyl-3-hydroxy-3-pyrroline-2-ones containing nitro group from aromatic aldehydes, 4-nitroaniline and sodium diethyl oxalacetate in absolute ethanol. Furthermore, the molecular structure of products has been proven via modern spectroscopic methods: nuclear magnetic resonance spectroscopy (1H NMR, 13C NMR) and electrospray ionization-high resolution mass spectrometry (ESI – HRMS).

Keywords

• γ-lactam ring
• 2-pyrrolidinone
• 3-pyrroline-2-one
• 1,5-dihydro-2h-pyrrol-2-one
• multi-component reaction