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Functionalized Tetrazoles from Cyanogen Azide with Secondary Amines
Author(s) -
Joo YoungHyuk,
Shreeve Jean'ne M.
Publication year - 2009
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.200900389
Subject(s) - chemistry , cyanogen , azide , tetrazole , steric effects , amine gas treating , cyanogen bromide , trimethylsilyl azide , acetonitrile , combinatorial chemistry , organic chemistry , biochemistry , peptide sequence , gene
Secondary amines react with cyanogen azide at ambient temperature in water/acetonitrile to provide tetrazole derivatives directly. The scope and limitations with regard to steric hindrance of the amine are discussed. Although reaction yields are moderate, 29–81 %, the cyanogen azide reactions provide a direct and versatile route to functionalized tetrazoles that may be especially useful considering the diversity of amines suitable for this transformation. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)