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.
Highlights
Multistep synthesis is the only possible choice for the preparation of highly complex natural products, it is important to keep in mind the actual feasibility and pragmatic aspects of those synthetic sequences
The identification of novel reactions enabling the one-pot assembly of compounds of medium structural complexity is an important field of research with significant implications for all chemistry branches [4]
In the light of these results, in Scheme 3 we propose the following reaction mechanism: the
Summary
Multistep synthesis is the only possible choice for the preparation of highly complex natural products, it is important to keep in mind the actual feasibility and pragmatic aspects of those synthetic sequences. A recent paper [1] demonstrated that for the famous 49 steps Woodward’s synthesis of chlorophyll a, 1 mg of product would have required 230 kg of ethyl acetoacetate, the first chemical used in that project. It is important, for concepts like “efficiency of synthesis” [2]. “reaction mass efficiency” [3], to consider the real practical application of any synthetic project For this reason, the identification of novel reactions enabling the one-pot assembly of compounds of medium structural complexity is an important field of research with significant implications for all chemistry branches [4]. When providing the desired chemical output, MCRs usually represent the most efficient choice available to chemists [5,6,7,8,9,10,11,12,13,14,15]
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