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•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.
Keywords: (3-indolyl)methyl ketones, indole-3-acetic acid, Weinreb amides, Grignard reaction, human arylhydrocarbon receptor.
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