61071-27-0Relevant academic research and scientific papers
Resin-bound thiophenols as S(N)AR-labile linkers: Application to the solid phase synthesis of aminopyridazines
Parrot, Isabelle,Wermuth, Camille-Georges,Hibert, Marcel
, p. 7975 - 7978 (1999)
A versatile approach for the solid phase synthesis of aminopyridazines was developed. Commercially available or novel resin-bound thiophenols are used to link 3,6-dichloropyridazine to solid supports and to introduce diversity into the molecule by direct cleavage of nucleophilic amines without oxidation to sulfones.
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.
