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DOI: 10.1055/s-0040-1706643
Synthesis of New Dialkyl 2,2′-[Carbonylbis(azanediyl)]dibenzoates via Curtius Rearrangement
The authors are greatly thankful to the National Centre for Scientific and Technical Research (CNRST) of Morocco and the University of Sultan Moulay Slimane, Beni-Mellal, Morocco for financial support.
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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.
Supporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0040-1706643.
- Supporting Information
Publication History
Received: 27 August 2020
Accepted after revision: 19 November 2020
Article published online:
11 January 2021
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