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

1
Dipartimento di Scienze del Farmaco, Università del Piemonte Orientale “A. Avogadro”, 28100 Novara, Italy
2
Dipartimento di Scienze Farmaceutiche, Università degli Studi di Milano, 20133 Milano, Italy
3
Dipartimento di Farmacia, Università degli Studi di Napoli “Federico II”, 80131 Napoli, Italy
*
Authors to whom correspondence should be addressed.
Molecules 2019, 24(10), 1959; https://doi.org/10.3390/molecules24101959
Received: 5 May 2019 / Revised: 16 May 2019 / Accepted: 20 May 2019 / Published: 21 May 2019
(This article belongs to the Special Issue Enabling Chemical Technologies in Medicinal Chemistry)
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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. View Full-Text
Keywords: multicomponent reactions; interrupted Ugi reactions; isocyanides multicomponent reactions; interrupted Ugi reactions; isocyanides
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Galli, U.; Hysenlika, R.; Meneghetti, F.; Del Grosso, E.; Pelliccia, S.; Novellino, E.; Giustiniano, M.; Tron, G.C. Exploiting the Nucleophilicity of the Nitrogen Atom of Imidazoles: One-Pot Three-Component Synthesis of Imidazo-Pyrazines. Molecules 2019, 24, 1959.

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