Synthesis p. 883 - 887 (1996)
Update date:2022-08-05
Topics:
Grumbach, Hans-Joachim
Arend, Michael
Risch, Nikolaus
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.
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