Curtius rearrangement

The Curtius rearrangement is a chemical reaction in which an acyl azide undergoes thermal decomposition to form an isocyanate and nitrogen gas. This reaction was first described by Curtius in 1890 and 1894. The resulting isocyanate can then be reacted with an amine to produce an aromatic urea.From: Sonochemistry [2018], An insight on the different synthetic routes for the facile synthesis of O/S-donor carbamide/thiocarbamide analogs and their miscellaneous pharmacodynamic applications [2023]

Organic Synthesis

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Published in Suresh C. Ameta, Rakshit Ameta, Garima Ameta, Sonochemistry, 2018

Chetna Ameta, Arpit Kumar Pathak, P. B. Punjabi

The Curtius rearrangement is the thermal decomposition of an acyl azide to an isocyanate with loss of nitrogen gas (Curtius, 1890 and 1894). Isocyanate then undergoes attack by a variety of nucleophiles, to yield a primary amine, carbamate, or urea derivative (Kaiser and Weinstock, 1988).

An insight on the different synthetic routes for the facile synthesis of O/S-donor carbamide/thiocarbamide analogs and their miscellaneous pharmacodynamic applications

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Published in Journal of Sulfur Chemistry, 2023

Faiza Asghar, Bushra Shakoor, Babar Murtaza, Ian S. Butler

The acyl azide is formed when chloroformate and sodium azide react with carboxylic acid, possibly through the formation of an azidoformate. The acyl azide undergoes a Curtius rearrangement to provide an isocyanate derivative, which was reacted with an amine to yield the aromatic urea (Scheme 16) [42]. One-pot racemization-free synthesis of ureas from carboxylic acids

Curtius rearrangement

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Organic Synthesis

An insight on the different synthetic routes for the facile synthesis of O/S-donor carbamide/thiocarbamide analogs and their miscellaneous pharmacodynamic applications