Aminoalkylation of Electron-Rich Aromatic Compounds Using Performed Iminium Salts Derived from Aldehydes other than Formaldehyde
- 1 July 1996
- journal article
- research article
- Published by Georg Thieme Verlag KG in Synthesis
- Vol. 1996 (07) , 883-887
- https://doi.org/10.1055/s-1996-4301
Abstract
Preformed iminium salts derived from aldehydes other than formaldehyde are demonstrated to be excellent reagents for the aminoalkylation of indoles, phenols and N,N-dimethylaniline. This method provides a simple and straightforward route to a variety of aromatic Mannich bases which are difficult to obtain by other procedures. Surprisingly, the reaction between N-methylindole or 2-naphthol with a preformed N-silyl iminium salt led to the formation of a bisindolylmethane or a dihydrooxazine derivative, respectively.Keywords
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