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

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.

SUBMITTER: Galli U

PROVIDER: S-EPMC6572241 | biostudies-literature | 2019 May

REPOSITORIES: biostudies-literature

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

Galli Ubaldina U Hysenlika Rejdia R Meneghetti Fiorella F Del Grosso Erika E Pelliccia Sveva S Novellino Ettore E Giustiniano Mariateresa M Tron Gian Cesare GC

Molecules (Basel, Switzerland) 20190521 10

A novel one-pot multicomponent reaction to synthesize substituted imidazopyrazines is described. In brief, 1<i>H</i>-(imidazol-5-yl)-<i>N</i>-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 ...[more]

PMID: 31117306

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