In the title compound, C17H16N2O5, the dihedral angles between the central urea [N—C(=O)—N] fragment and its attached benzene rings are 20.20 (14) and 24.24 (13)°; the dihedral angle between the aromatic rings is 42.1 (1)°. The molecular conformation is consolidated by two intramolecular N—H⋯O hydrogen bonds, which both generate S(6) rings. In the crystal, inversion dimers linked by pairs of C—H⋯O interactions generate R
2
2(14) loops. The dimers are linked by further C—H⋯O interactions into (011) sheets.
The 2-(alkylcarbonyl)benzoic acids obtained by esterification of phthalic anhydride are converted into azide derivatives: alkyl 2-[(azidocarbonyl)amino]benzoates and to ureas: dialkyl 2,2′-[carbonylbis(azanediyl)]dibenzoates. These transformations were carried out using classical Curtius rearrangement conditions in the presence of diphenylphosphoryl azide (DPPA) in a basic medium, followed by hydrolysis. Subsequently, a final condensation reaction of these urea derivatives enabled us to obtain, for the first time, the new alkyl derivatives, alkyl 2-[2,4-dioxo-1,2-dihydroquinazolin-3(4H)-yl]benzoates. All the new compounds obtained in satisfactory yields were characterized by 1H and 13C NMR, and by X-ray crystallographic analysis.
In the almost planar (r.m.s. deviation = 0.038 Å) title compound, C10H10N4O3, an intramolecular N—H...O interaction closes anS(6) ring. In the crystal, aromatic π–π stacking interactions occur [inter-centroid distance = 3.65 (2) Å].
The title compound, C12H14N4O3, is planar with an r.m.s deviation of 0.025 Å from the plane through all 19 non-hydrogen atoms. An intramolecular N—H...O interaction closes anS(6) ring. In the crystal, molecules are linked by C—H...π and weak offset π–π stacking interactions [inter-centroid distance = 3.614 (2) Å], forming undulating sheets parallel to (001).
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