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Amination, III. Trimethylsilanol as Leaving Group, V. Silylation - Amination of Hydroxy N-Heterocycles
Vorbrueggen, Helmut,Krolikiewicz, Konrad
, p. 1523 - 1541 (2007/10/02)
Hydroxy N-heterocycles such as 18, 21, 26, and others are efficiently aminated in a one-step/one-pot procedure by silylation-amination to give 20, 23 - 25 etc.Silylation converts aromatic hydroxy N-heterocycles into activated and lipophilic intermediates of type 3, 8 which react in situ with ammonia, primary or secondary amines to form the corresponding mono-, bis- or tris-aminated products (5, 10).This addition-elimination of amines to O-silylated heterocycles is Lewis acid-catalysed and proceeds usually in high yields if the leaving group trimethylsilanol is converted in situ by excess silylated agent into hexamethyldisiloxane.Scope and limitations of this simple procedure are discussed.
