Intermolecular trapping by indole of a spiroindolenine intermediate formed during the Bischler-Napieralski cyclisation of N-acetyltryptamine
The Bischler-Napieralski cyclisation of N-acetyltryptamine (1a) in the presence of indole (15) affords a moderate yield of the diastereomeric spiroindolines 9 and 10 suggesting the intermediacy of a spiroindolenine 2a in this reaction. Evidence is provided to show that the minor reaction products 2-methyltryptamine (11), tris-(3-indolyl)methane (12) and 6-[(o-aminophenyl) methyl]-5,11-dihydroindolo[3,2-b]carbazole (13) are derived from the spiroindolines 9 and 10.
Frost, Jonathan R.,Gaudilliere, Bernard R.P.,Kauffmann, Elisabeth,Loyaux, Denis,Normand, Nadine,Petry, Genevieve,Poirier, Philippe,Wenkert, Ernest,Wick, Alexander E.
p. 175 - 182
(2007/10/02)
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