Heterocyclic Compounds
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ChemInform Abstract: A New Approach to 4-(2-Aminoethyl)indoles via Claisen ortho-Amide Rearrangement of 3-Hydroxy-2-methoxyindolines.
First published: November 27, 1990
Abstract
The hydroxyindolines (I) react with the amide acetal (II) in o-dichlorobenzene to produce a mixture of the aromatic N,N-dimethylacetamides (III) and (IV).
ChemInform Abstract
The hydroxyindolines (I) react with the amide acetal (II) in o-dichlorobenzene to produce a mixture of the aromatic N,N-dimethylacetamides (III) and (IV). Elimination of methanol from (IIIa) gives the N-acetylindole (V) which is deprotected upon treatment with a base, forming the indole (IVa). Reduction of the carboxamide (IVa) with lithium alanate yields the amine (VI).
