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Opietnik, M; Jungbauer, A; Mereiter, K; Rosenau, T.
(2013): Synthesis of 2-(Indol-3-yl)-ethanone-based Arylhydrocarbon Receptor Agonist Candidates via Weinreb Amides of Indole-3-acetic Acid
CURR ORG SYNTH. 2013; 10(5): 812-818.

Abstract:: Grignard reactions with the Weinreb amide (N-methoxy-N-methylamide) of indole-3-acetic acid provide a facile access to indol-3-yl ketones, which are potential agonists of the human aryl hydrocarbon receptor ("dioxin receptor"). Addition of one equivalent of the MgBr2 center dot THF complex avoids discolorations and oxidative side reactions, for which the 3-indolyl system is notorious. The product ketones carry aliphatic, olefinic, as well as (hetero)aromatic residues. The reaction conditions were thoroughly optimized, and full sets of analytical data including example crystal structures are presented.
Authors BOKU Wien:: Jungbauer Alois; Rosenau Thomas
Find related publications in this database (Keywords): (3-indolyl)methyl ketones; indole-3-acetic acid; Weinreb amides; Grignard reaction; human arylhydrocarbon receptor