Synthetically useful aminodioximes are prepared via a novel three-component reaction among Z-chlorooxirnes, isocyanides, and hydroxylamines by exploiting the preferential attack of isocyanides to nitrile N-oxides via a [3 + 1] cycloaddition reaction. The results of quantum mechanical studies of the reaction mechanism are also discussed. Furthermore, the one-pot conversion of aminodioximes to 1,2,3-oxadiazole-5-amines via Mitsunobu-Beckmann rearrangement is reported for the first time.
|Titolo:||A multicomponent reaction among Z-chlorooximes, isocyanides, and hydroxylamines as iper-nucleophile third component. A one-pot access to aminodioximes and their subsequent transformation to 1,2,4-oxadiazole-5-amines through a Mitsunobu-Beckmann rearrangement|
|Settore Scientifico Disciplinare:||Settore CHIM/08 - Chimica Farmaceutica|
|Data di pubblicazione:||set-2015|
|Digital Object Identifier (DOI):||10.1021/acs.joc.5b01676|
|Appare nelle tipologie:||01 - Articolo su periodico|