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Curtius Rearrangement of Aromatic Carboxylic Acids to Access Protected Anilines and Aromatic Ureas

Hélène Lebel* and Olivier Leogane

*Département de chimie, Université de Montréal, P.O. Box 6128, Station Downtown, Montréal, Québec, Canada, H3C 3J7, Email: helene.lebelumontreal.ca

H. Lebel, O. Leogane, Org. Lett., 2006, 8, 5717-5720.

DOI: 10.1021/ol0622920 (free Supporting Information)


Abstract

The reaction of di-tert-butyl dicarbonate or a chloroformate and sodium azide with an aromatic carboxylic acid produces the corresponding acyl azide. The acyl azide undergoes a Curtius rearrangement to form an isocyanate derivative which is trapped either by an alkoxide or by an amine to form the aromatic carbamate or urea.

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Boc-Protected Amines via a Mild and Efficient One-Pot Curtius Rearrangement

H. Lebel, O. Leogane, Org. Lett., 2005, 7, 4107-4110.


Key Words

Curtius Rearrangement, aryl amines, carbamates, tert-butyl carbamates, ureas


ID: J54-Y2006-3890