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.
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 / V. Mercalli, A. Massarotti, M. Varese, M. Giustiniano, F. Meneghetti, E. Novellino, G.C. Tron. - In: JOURNAL OF ORGANIC CHEMISTRY. - ISSN 0022-3263. - 80:19(2015 Sep), pp. 9652-9661. [10.1021/acs.joc.5b01676]
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
F. Meneghetti;
2015
Abstract
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.
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