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Chemoselective Palladium‐Catalyzed Direct C–H Arylation of 5‐Carboxyimidazoles: Unparalleled Access to Fused Imidazole‐Based Tricycles Containing Six‐, Seven‐ or Eight‐Membered Rings

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An extensive study of the chemoselective Pd-catalyzed inter- and intramolecular direct C–H arylation of N-benzylated 5-carboxyimidazoles with halides with and without CuI assistance in 1,4-dioxane as a low-polarity solvent was… Click to show full abstract

An extensive study of the chemoselective Pd-catalyzed inter- and intramolecular direct C–H arylation of N-benzylated 5-carboxyimidazoles with halides with and without CuI assistance in 1,4-dioxane as a low-polarity solvent was explored. The method was suitable for the synthesis of fused imidazole-based tricyclic systems incorporating medium-sized rings, including, for the first time, eight-membered rings, which are valuable in modern drug design.

Keywords: direct arylation; membered rings; fused imidazole; eight membered; imidazole based

Journal Title: European Journal of Organic Chemistry
Year Published: 2017

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