Synthesis 2021; 53(11): 1971-1979
DOI: 10.1055/s-0040-1706643
paper

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

Hasna Yassine
a   Laboratoire de Chimie Organique et Analytique, Université Sultan Moulay Slimane - Faculté des Sciences et Techniques, BP 523, 23000 Beni-Mellal, Morocco
,
Jamila Bouali
a   Laboratoire de Chimie Organique et Analytique, Université Sultan Moulay Slimane - Faculté des Sciences et Techniques, BP 523, 23000 Beni-Mellal, Morocco
,
Asmaa Oumessaoud
a   Laboratoire de Chimie Organique et Analytique, Université Sultan Moulay Slimane - Faculté des Sciences et Techniques, BP 523, 23000 Beni-Mellal, Morocco
b   Laboratori de Química Farmacèutica, Facultat de Farmàcia, Universitat de Barcelona, Av. Joan XXIII, 27-31, 08028 Barcelona, Spain
,
El Mahdi Ourhzif
a   Laboratoire de Chimie Organique et Analytique, Université Sultan Moulay Slimane - Faculté des Sciences et Techniques, BP 523, 23000 Beni-Mellal, Morocco
c   Université Clermont-Auvergne, CNRS, SIGMA Clermont, ICCF, 63000 Clermont–Ferrand, France
,
Salha Hamri
a   Laboratoire de Chimie Organique et Analytique, Université Sultan Moulay Slimane - Faculté des Sciences et Techniques, BP 523, 23000 Beni-Mellal, Morocco
d   Laboratoire de Chimie Organique, Organométallique et Valorisation des Substances Naturelles, Faculté des Sciences Agadir, BP 8106, Cité Dakhla Agadir 80000, Université Ibn Zohr, Maroc
,
Abderrafia Hafid
a   Laboratoire de Chimie Organique et Analytique, Université Sultan Moulay Slimane - Faculté des Sciences et Techniques, BP 523, 23000 Beni-Mellal, Morocco
,
Mostafa Khouili
a   Laboratoire de Chimie Organique et Analytique, Université Sultan Moulay Slimane - Faculté des Sciences et Techniques, BP 523, 23000 Beni-Mellal, Morocco
,
b   Laboratori de Química Farmacèutica, Facultat de Farmàcia, Universitat de Barcelona, Av. Joan XXIII, 27-31, 08028 Barcelona, Spain
› Author Affiliations
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.


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



Publication History

Received: 27 August 2020

Accepted after revision: 19 November 2020

Article published online:
11 January 2021

© 2021. Thieme. All rights reserved

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