Efficient Conversion of Aromatic Amines into Azides:  A One-Pot Synthesis of Triazole Linkages

Karine Barral, Adam D. Moorhouse, and John E. Moses*
Department of Pharmaceutical and Biological Chemistry. The School of Pharmacy, University of London, 29-39 Brunswick Square, London, WC1N 1AX, United Kingdom
Org. Lett., 2007, 9 (9), pp 1809–1811
DOI: 10.1021/ol070527h
Publication Date (Web): March 29, 2007
Copyright © 2007 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.

, john.moses@pharmacy.ac.uk

Abstract

Abstract Image

An efficient and improved procedure for the preparation of aromatic azides and their application in the Cu(I)-catalyzed azide−alkyne 1,3-dipolar cycloaddition (“click reaction”) is described. The synthesis of aromatic azides from the corresponding amines is accomplished under mild conditions with tert-butyl nitrite and azidotrimethylsilane. 1,4-Disubstituted 1,2,3-triazoles were obtained in excellent yields from a variety of aromatic amines without the need for isolation of the azide intermediates.

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History

  • Published In Issue April 26, 2007
  • Received March 2, 2007

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