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

Hélène Lebel* and Olivier Leogane
Dpartement de chimie, Universit de Montral, P.O. Box 6128, Station Downtown, Montral, Qubec, Canada, H3C 3J7
Org. Lett., 2006, 8 (25), pp 5717–5720
DOI: 10.1021/ol0622920
Publication Date (Web): November 16, 2006
Copyright © 2006 American Chemical Society
*

In papers with more than one author, the asterisk indicates the name of the author to whom inquiries about the paper should be addressed.

, helene.lebel@umontreal.ca

Abstract

Abstract Image

The reaction of a chloroformate or di-tert-butyl dicarbonate and sodium azide with an aromatic carboxylic acid produces the corresponding acyl azide, presumably through the formation of an azidoformate. 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. The reaction conditions are compatible with a variety of functional groups and allow the synthesis of a number of aniline derivatives containing alkyl, halide, nitro, ketone, ether, and thioether substituents.

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History

  • Published In Issue December 07, 2006
  • Received September 18, 2006

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