19862-46-5Relevant academic research and scientific papers
Copper-Catalyzed Carbonyl Group Controlled Coupling of Isatin Oximes with Arylboronic Acids To Prepare N-Aryloxindole Nitrones
Mo, Xue-Ling,Chen, Chun-Hua,Liang, Cui,Mo, Dong-Liang
, p. 150 - 159 (2018)
A variety of (E)-N-aryloxindole nitrones were prepared in good to excellent yields by using a copper-catalyzed coupling reaction of isatin oximes and arylboronic acids under mild conditions. Various arylboronic acids that contain sensitive functional groups were tolerated in the transformation, and detailed studies show that the carbonyl group of the isatin oximes serves as a ligand to control the formation of the (E)-oxindole nitrones. This method to prepare (E)-N-aryloxindole nitrones was easily performed on a gram scale and efficiently used to synthesize estrone-derived oxindole nitrone in high yield.
Nitrones and nucleobase-containing spiro-isoxazolidines derived from isatin and indanone: Solvent-free microwave-assisted stereoselective synthesis and theoretical calculations
Maiuolo, Loredana,Merino, Pedro,Algieri, Vincenzo,Nardi, Monica,Di Gioia, Maria Luisa,Russo, Beatrice,Delso, Ignacio,Tallarida, Matteo Antonio,De Nino, Antonio
, p. 48980 - 48988 (2017/11/06)
The spiro-oxindoles have found wide application because of their antiviral properties. However, in the literature few examples of synthesis of their precursors, oxindole-nitrones, are reported. In this paper, we initially present a rapid and efficient synthetic approach to ketonitrones by solvent-free microwave-assisted reaction between isatin or indanone derivatives and various hydroxylamines. The synthetic protocol is facile, clean, fast, high-yielding and stereoselective. Then, we explored the possibility to synthesize nucleobase-containing spiro-isoxazolidines with isatin and indanone nuclei by solvent-free MW-assisted 1,3-dipolar cycloaddition, obtaining good results in yields (74-85%), and regio- and diastereoselectivity. Theoretical calculations were done to analyze the difference of reactivity of isatin and indanone derivatives with hydroxylamines.
