Aminoalkylation of Electron-Rich Aromatic Compounds Using Performed Iminium Salts Derived from Aldehydes other than Formaldehyde

Hans-Joachim Grumbach; Michael Arend; Nikolaus Risch

doi:10.1055/s-1996-4301

Synthesis 1996; 1996(7): 883-887
DOI: 10.1055/s-1996-4301

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Aminoalkylation of Electron-Rich Aromatic Compounds Using Performed Iminium Salts Derived from Aldehydes other than Formaldehyde

Hans-Joachim Grumbach, Michael Arend, Nikolaus Risch^*

^*Fachbereich Chemie und Chemietechnik der Universität-Gesamthochschule Paderborn, Warburger Str. 100, D-33098 Paderborn, Germany, Fax +5251/60-3245; E-mail: nr@chemie.uni-paderborn.de

Abstract

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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.

aminoalkylation - iminium salts - indoles - Mannich basis - phenols

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