Exploiting the Nucleophilicity of the Nitrogen Atom of Imidazoles: One-Pot Three-Component Synthesis of Imidazo-Pyrazines

利用咪唑氮原子的亲核性:一锅法三组分合成咪唑并吡嗪

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作者:Ubaldina Galli, Rejdia Hysenlika, Fiorella Meneghetti, Erika Del Grosso, Sveva Pelliccia, Ettore Novellino, Mariateresa Giustiniano, Gian Cesare Tron

Abstract

A novel one-pot multicomponent reaction to synthesize substituted imidazopyrazines is described. In brief, 1H-(imidazol-5-yl)-N-substituted methanamines react with aldehydes and isocyanides in methanol at room temperature to give imidazopyrazine derivatives in excellent yields. The imidazole nitrogen atom was able to intercept the nascent nitrilium ion, channeling the reaction toward to the sole formation of imidazopyrazines, suppressing the competitive formation of other possible side products deriving from the reaction with the high-energy nitrilium ion. The number of examples and the variability of the nature of isocyanides, aldehydes, and amine components herein employed, witness the robustness of this novel methodology.

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