An operationally simple multicomponent reaction utilizing (Z)-chloroximes, isocyanides and NH-heterocyclic 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.
Multicomponent reaction between (Z)-chloroximes, isocyanides and NH-heterocyclic rings
Brunelli F.;Galli U.;Tron G. C.
2021-01-01
Abstract
An operationally simple multicomponent reaction utilizing (Z)-chloroximes, isocyanides and NH-heterocyclic 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.I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.
