Multicomponent reaction between (Z)-chloroximes, isocyanides and NH-heterocyclic rings

An operationally simple multicomponent reaction utilizing (Z)-chloroximes, isocyanides and NH-hetero-cyclic rings (imidazole, benzimidazole, triazole, benzotriazole and tetrazole) affords a hitherto unknown class of compounds which cannot be obtained via a classical multistep two-component reaction. From this work, it appears evident: a) kinetic control dictated by the [3 + 1] cycloaddition between nitrile N-oxides and isocyanides; b) the chemical compatibility between the highly unstable nitrilium ion and the poorly nucleophilic imidazoles and related heterocycles, which quench the reaction allowing for the formation of a single product. (c) 2021 Elsevier Ltd. All rights reserved.