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 b
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- 作者：Valentina Mercalli ; Alberto Massarotti ; Monica Varese ; Mariateresa Giustiniano ; Fiorella Meneghetti ; Ettore Novellino ; Gian Cesare Tron
- 刊名：Journal of Organic Chemistry
- 出版年：2015
- 出版时间：October 2, 2015
- 年：2015
- 卷：80
- 期：19
- 页码：9652-9661
- 全文大小：461K
- ISSN：1520-6904
文摘
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鈥揃eckmann rearrangement is reported for the first time.