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

• Published in: Results in Chemistry 2020-01, Vol.2, p.100042, Article 100042
• Main Authors: Saaed, Wessam, Elagawany, Mohamed, Azab, Mohamed M., Amin, Alaa S., Rath, Nigam P., Hegazy, Lamees, Elgendy, Bahaa
• Format: Article
• Language: English
• Subjects: Cyclization reactions; DFT method; Imidazolinone; Single crystal; Solvent-free
• ISSN: 2211-7156; 2211-7156
• DOI: 10.1016/j.rechem.2020.100042

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. •Solvent-and catalyst free cyclization for the synthesis of 1-arylidenamino-2-imidazoline-ones has been developed.•The novel method is simple, practical, efficient, and gives good yields.•Single crystal X-ray structure of 2d shows that the compound crystallizes in the triclinic space group P-1 with Z = 2.•The global chemical reactivity descriptors of 2d were calculated and shows this compound have good stability, high excitation energy, and high electrophilicity.