Efficient conversion of aromatic amines into azides: a one-pot synthesis of triazole linkages.
[reaction: see text] 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.
Barral
Karine
K
Department of Pharmaceutical and Biological Chemistry. The School of Pharmacy, University of London, 29-39 Brunswick Square, London, WC1N 1AX, United Kingdom.
Moorhouse
Adam D
AD
Moses
John E
JE
D000588:Amines / Q000737:chemistry*; D001386:Azides / Q000138:chemical synthesis* / Q000737:chemistry; D003432:Cross-Linking Reagents / Q000737:chemistry*; D015394:Molecular Structure; D014230:Triazoles / Q000737:chemistry*
D000588:Amines; D001386:Azides; D003432:Cross-Linking Reagents; D014230:Triazoles