TY - JOUR
T1 - 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
AU - Mercalli, Valentina
AU - Massarotti, Alberto
AU - Varese, Monica
AU - Giustiniano, Mariateresa
AU - Meneghetti, Fiorella
AU - Novellino, Ettore
AU - Tron, Gian Cesare
N1 - Publisher Copyright:
© 2015 American Chemical Society.
PY - 2015/10/2
Y1 - 2015/10/2
N2 - 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.
AB - 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.
UR - https://www.scopus.com/pages/publications/84942896567
U2 - 10.1021/acs.joc.5b01676
DO - 10.1021/acs.joc.5b01676
M3 - Article
SN - 0022-3263
VL - 80
SP - 9652
EP - 9661
JO - Journal of Organic Chemistry
JF - Journal of Organic Chemistry
IS - 19
ER -