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

Valentina Mercalli, Alberto Massarotti, Monica Varese, Mariateresa Giustiniano*, Fiorella Meneghetti, Ettore Novellino and Gian Cesare Tron*

*Università degli Studi del Piemonte Orientale, Largo Donegani 2, 28100 Novara; Università degli Studi di Napoli, via D. Montesano 49, 80131 Napoli, Italy, Email: mariateresa.giustinianounina.it, giancesare.tronpharm.unipmn.it

V. Mercalli, A. Massarotti, M. Varese, M. Giustiniano, F. Meneghetti, E. Novellino, G. C. Tron, J. Org. Chem., 2015, 80, 9652-9661.

DOI: 10.1021/acs.joc.5b01676

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Abstract

Synthetically useful aminodioximes are prepared via a novel three-component reaction of Z-chlorooximes, isocyanides, and hydroxylamines. Furthermore, a Mitsunobu-Beckmann rearrangement of aminodioximes yields 1,2,3-oxadiazole-5-amines.

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Key Words

1,2,4-oxadiazoles

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ID: J42-Y2015