title: Multicomponent Reaction of Z-Chlorooximes, Isocyanides, and Hydroxylamines as Hypernucleophilic Traps. A One-Pot Route to Aminodioximes and Their Transformation into 5-Amino-1,2,4-oxadiazoles by Mitsunobu-Beckmann Rearrangement.
abstract: Synthetically useful aminodioximes are prepared via a novel three-component reaction among Z-chlorooximes, 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.
authors.affiliation: Dipartimento di Scienze del Farmaco, Università degli Studi del Piemonte Orientale "A. Avogadro" , Largo Donegani 2, 28100 Novara, Italy.
authors.forename: Valentina
authors.initials: V
authors.lastname: Mercalli
authors.affiliation: Dipartimento di Scienze del Farmaco, Università degli Studi del Piemonte Orientale "A. Avogadro" , Largo Donegani 2, 28100 Novara, Italy.
authors.forename: Alberto
authors.initials: A
authors.lastname: Massarotti
authors.affiliation: Dipartimento di Scienze del Farmaco, Università degli Studi del Piemonte Orientale "A. Avogadro" , Largo Donegani 2, 28100 Novara, Italy.
authors.forename: Monica
authors.initials: M
authors.lastname: Varese
authors.affiliation: Dipartimento di Farmacia, Università degli Studi di Napoli "Federico II" , via D. Montesano 49, 80131 Napoli, Italy.
authors.forename: Mariateresa
authors.initials: M
authors.lastname: Giustiniano
authors.affiliation: Dipartimento di Scienze Farmaceutiche, Università degli Studi di Milano , Via L. Mangiagalli 25, 20133, Milano, Italy.
authors.forename: Fiorella
authors.initials: F
authors.lastname: Meneghetti
authors.affiliation: Dipartimento di Farmacia, Università degli Studi di Napoli "Federico II" , via D. Montesano 49, 80131 Napoli, Italy.
authors.forename: Ettore
authors.initials: E
authors.lastname: Novellino
authors.affiliation: Dipartimento di Scienze del Farmaco, Università degli Studi del Piemonte Orientale "A. Avogadro" , Largo Donegani 2, 28100 Novara, Italy.
authors.forename: Gian Cesare
authors.initials: GC
authors.lastname: Tron