4.5 Article

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

Journal

SYNTHESIS-STUTTGART
Volume 53, Issue 11, Pages 1971-1979

Publisher

GEORG THIEME VERLAG KG
DOI: 10.1055/s-0040-1706643

Keywords

phthalic anhydride; Curtius rearrangement; azide; acyl azide; urea

Funding

  1. National Centre for Scientific and Technical Research (CNRST) of Morocco
  2. University of Sultan Moulay Slimane, Beni-Mellal, Morocco

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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.
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.

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