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Amination, III. Trimethylsilanol as Leaving Group, V. Silylation—Amination of Hydroxy N‐Heterocycles
Author(s) -
Vorbrüggen Helmut,
Krolikiewicz Konrad
Publication year - 1984
Publication title -
chemische berichte
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.667
H-Index - 136
eISSN - 1099-0682
pISSN - 0009-2940
DOI - 10.1002/cber.19841170421
Subject(s) - chemistry , silylation , amination , hexamethyldisiloxane , organic chemistry , reductive amination , morpholine , primary (astronomy) , ammonia , lewis acids and bases , leaving group , catalysis , medicinal chemistry , physics , plasma , quantum mechanics , astronomy
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 in Lewis acid‐catalyzed 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.