Catalyst-and organic solvent-free synthesis, structural, and theoretical studies of 1-arylidenamino-2,4-disubstituted-2-imidazoline-5-ones

• Main Authors: Wessam Saaed, Mohamed Elagawany, Mohamed M. Azab, Alaa S. Amin, Nigam P. Rath, Lamees Hegazy, Bahaa Elgendy
• Format: Article
• Language: English
• Published: Elsevier 2020-01-01
• Series: Results in Chemistry
• Subjects: Solvent-free; Imidazolinone; Cyclization reactions; Single crystal; DFT method
• Online Access: http://www.sciencedirect.com/science/article/pii/S2211715620300205
• ISSN: 2211-7156

We have developed a solvent- and catalyst-free cyclization reaction for the synthesis of 1-arylidenamino-2,4-disubstituted-2-imidazoline-5-ones under neat conditions. The new synthetic procedure is efficient and green in nature. All synthesized compounds were obtained in good yields (70–78%) and have been characterized by 1H and 13C NMR spectroscopy. The structure of compound 2d was characterized crystallographically using a single crystal X-Ray diffractometer. Compound 2d was found to crystallize in the triclinic space group P-1 with Z = 2. Moreover, the Frontier Molecular Orbitals (FMOs), the global chemical reactivity descriptors, and the molecular Electrostatic Potential (MEP) of 2d have been calculated at B3LYP/6-31G(d,p) level of theory.