期刊
RSC ADVANCES
卷 7, 期 77, 页码 48980-48988出版社
ROYAL SOC CHEMISTRY
DOI: 10.1039/c7ra09995a
关键词
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资金
- Italian Ministry of University and Scientific Research (MIUR)
- University of Calabria
- FEDER Program (Madrid, Spain) [CTQ2016-76155-R]
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.
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