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Synthesis 1995; 1995(10): 1225-1227
DOI: 10.1055/s-1995-4081
short paper
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Regioselective Metalation of 9-Methoxymethyl-β-carboline-3-carboxamides with Amidomagnesium Chlorides

Wolfgang Schlecker, Andreas Huth, Eckhard Ottow, Johann Mulzer*
  • *Institut für Organische Chemie der Freien Universität, Takustrasse 3, D-14195 Berlin, Germany, Fax +49(30)8385163
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Publication Date:
31 December 2000 (online)

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The N-protected β-carbolines 3 and 4 undergo exclusive metalation at C-4 with 2,2,6,6-tetramethylpiperidinomagnesium chloride (TMPMgCl) and/or diethylamidomagnesium chloride, whereas the unprotected β-carboline 8 is inert under these conditions. The C-4 metalated species react with electrophiles to give 3,4-disubstituted β-carbolines, which are interesting precursors to physiologically active compounds.

ortho-magnesiation - regioselective ortho-metalation - β-carboline-3-carboxamide - 2,2,6,6-tetramethylpiperidinomagnesium