SYNTHESIS, CRYSTAL STRUCTURE, AND DFT STUDIES OF ETHYL 4-HYDROXY-2-(4-METHOXYPHENYL)-5-OXO- 1-PHENYL-2,5-DIHYDRO-1H-PYRROLE-3-CARBOXYLATE

Abstract

An efficient method for the synthesis of a new highly substituted pyrrolidinone derivative is developed via a three-component one-pot reaction of aniline, diethyl acetylenedicarboxylate, and 4-anisaldehyde. The structure of ethyl 4-hydroxy-2-(4-methoxyphenyl)-5-oxo-1-phenyl-2,5-dihydro-1H-pyrrole-3-carboxylate is confirmed by FTIR, 1H and 13C NMR spectroscopy. Unambiguous evidence for the structure of the synthesized product is obtained from the single crystal X-ray analysis. The comparison of both its molecular structure and intermolecular interactions with the previously known analogous compounds reveals that the mutual syn- or antiperiplanar orientation of ester C=O and pyrrolinone-bound OH is related to the type of molecular dimers formed in the solid state. The geometrical structure, the HOMO–LUMO analysis (electrophilicity index), 1H and 13C chemical shifts of the desired product are also calculated by DFT at the B3LYP level with the 6-31++G(d,p) basis set. The calculated chemical shifts are in compliance with the experimental data.

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Funding

This work was supported by Islamic Azad University, Abhar Branch and University of Zanjan.

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Ahankar, H., Ramazani, A., Saeidian, H. et al. SYNTHESIS, CRYSTAL STRUCTURE, AND DFT STUDIES OF ETHYL 4-HYDROXY-2-(4-METHOXYPHENYL)-5-OXO- 1-PHENYL-2,5-DIHYDRO-1H-PYRROLE-3-CARBOXYLATE. J Struct Chem 62, 47–57 (2021). https://doi.org/10.1134/S0022476621010066

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Keywords

  • pyrrolidinone derivative
  • multicomponent reaction
  • single crystal X-ray analysis
  • density functional theory
  • electrophilicity index.