Synthesis of New Dialkyl 2,2′-[Carbonylbis(azanediyl)]dibenzoates via Curtius Rearrangement

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 H-1 and C-13 NMR, and by X-ray crystallographic analysis.

Automated summary

The 2-(alkylcarbonyl)benzoic acids obtained by esterification of phthalic anhydride can be converted into azide derivatives and ureas, leading to the synthesis of new alkyl derivatives. These new compounds were characterized by H-1 and C-13 NMR, as well as X-ray crystallographic analysis.