New Route to Direct Synthesis of Symmetrical Ureas from Carboxylic Acids

Daniel Jahani; Hasna Yassine; Mostafa Khouili; M. Dolors Pujol

doi:10.1055/a-2172-8329

Synthesis, Inhaltsverzeichnis

Synthesis 2024; 56(01): 143-150
DOI: 10.1055/a-2172-8329

paper

New Route to Direct Synthesis of Symmetrical Ureas from Carboxylic Acids

Daniel Jahani

^aLaboratori de Química Farmacèutica, Facultat de Farmàcia i Ciències de l’Alimentació, Universitat de Barcelona, Av. Joan XXIII, 27–31 08028 Barcelona, Spain URL: mdpujol@ub.edu

,

Hasna Yassine

^bMolecular Chemistry, Materials and Catalysis Laboratory, Faculty of Sciences and Technologies, Sultan Moulay Slimane University, BP 523, 23000 Beni-Mellal, Morocco

,

Mostafa Khouili

^bMolecular Chemistry, Materials and Catalysis Laboratory, Faculty of Sciences and Technologies, Sultan Moulay Slimane University, BP 523, 23000 Beni-Mellal, Morocco

,

M. Dolors Pujol ∗

^aLaboratori de Química Farmacèutica, Facultat de Farmàcia i Ciències de l’Alimentació, Universitat de Barcelona, Av. Joan XXIII, 27–31 08028 Barcelona, Spain URL: mdpujol@ub.edu

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Abstract

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Abstract

The first method for the direct conversion of carboxylic acids into ureas has been developed. The classical procedures described for the formation of ureas from carboxylic acids require two steps, preparation of the isocyanate followed by its aminolysis. In this work, aryl carboxylic and arylalkyl carboxylic acids have been transformed into symmetric ureas in a single step using DPPA or sodium azide as nitrogen source. The addition of water (method A) or the presence of solvent water (method B) was essential for the formation of symmetrical ureas from the corresponding carboxylic acids. The corresponding ureas have been obtained in good to excellent yields of 46 to 100%. This procedure is compatible with different substituents present in the starting carboxylic acid.

Key words

urea - carboxylic acid - isocyanate - DPPA - sodium azide

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