Synthesis and DFT Quantum Chemical Calculations of 2-Oxopyrimidin-1(2H)-yl-Urea and Thiorea Derivatives

Abstract

A series of the new 2-oxopyrimidin-1(2H)-yl-urea (3a-c) and thiourea (4a-d) derivatives were synthesized by the reaction of arylisocyanates (2a-c) or arylisothiocyanates (2d-g) and the 1-amino-5-(4-methoxybenzoyl)-4-(4-methoxyphenyl)pyrimidin-2(1H)-one (1). The structures of the compounds 3a-c and 4a-d were characterized by elemental analysis, FT-IR, 1H and 13C-NMR spectroscopic techniques. In addition to experimental study in order to find molecular properties, quantum-chemical calculations of the synthesized compounds were carried out by using DFT/B3LYP method with basis set of the 6-311G(d,p). Quantum chemical features such as HOMO, LUMO, HOMO-LUMO energy gap, Ionization potential, chemical hardness, chemical softness, electronegativity, chemical potential, dipole moment etc. values for gas and solvent phase of neutral molecules were calculated and discussed.

Design, Synthesis, Cytotoxic Activity, and In Silico Studies of New Schiff Bases Including Pyrimidine Core

“…In recent years, the reactions of aminopyrimidine‐2‐one/thione derivatives with isothiocyanate, [4] 1,3‐dicarbonyl compounds, [5] aryl chlorides, [6] various Schiff bases and transition metal complexes [7] have been reported. Nowadays, theoretical, and experimental comparison of N‐aminopyrimidine‐2‐one derivatives have become popular [4b,8] …”

A New Schiff Base Molecule Prepared from Pyrimidine-2-thione: Synthesis, Spectral Characterization, Cytotoxic Activity, DFT, and Molecular Docking Studies

“…Aminopyrimidine-2-one/thione derivatives appeared to be an important starting compound in synthetic organic chemistry. In recent years, the reactions of aminopyrimidine-2one/thione derivatives with isothiocyanate [14,15], 1,3-dicarbonyl compounds [16], aryl chlorides [17] and transition metal complexes [18,19] have been reported. Nowadays, theoretical, and experimental comparison of N-aminopyrimidine-2-one derivatives have become popular [15,20,21].…”

“…In recent years, the reactions of aminopyrimidine-2one/thione derivatives with isothiocyanate [14,15], 1,3-dicarbonyl compounds [16], aryl chlorides [17] and transition metal complexes [18,19] have been reported. Nowadays, theoretical, and experimental comparison of N-aminopyrimidine-2-one derivatives have become popular [15,20,21]. Therefore, in the present study, the starting material 1 was obtained from the reaction of furan-2,3-dione and acetophenone thiosemicarbazone according to the procedure in the literature [17] (Scheme 1).…”