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

Abstract

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.

Key words

phthalic anhydride - Curtius rearrangement - azide - acyl azide - urea

Publication History

Received: 27 August 2020

Accepted after revision: 19 November 2020

Article published online:
11 January 2021

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