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Synthesis of 2-(Indol-3-yl)-ethanone-based Arylhydrocarbon Receptor Agonist Candidates via Weinreb Amides of Indole-3-acetic Acid.

[ Vol. 10 , Issue. 5 ]

Author(s):

Martina Opietnik, Alois Jungbauer, Kurt Mereiter and Thomas Rosenau   Pages 812 - 818 ( 7 )

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•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.

Affiliation:

University of Natural Resources and Life Sciences, Department of Chemistry, Muthgasse 18, A-1190 Vienna, Austria.



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