Journal of Organic Chemistry
Journal of Organic Chemistry
4 years ago

P(NMe2)3-Mediated Reductive (1 + 4) Annulation Reaction of Isatins with Nitroalkenes: An Access to Spirooxindolyl Isoxazoline N-Oxides and Their Corresponding Isoxazolines

P(NMe2)3-Mediated Reductive (1 + 4) Annulation Reaction of Isatins with Nitroalkenes: An Access to Spirooxindolyl Isoxazoline N-Oxides and Their Corresponding Isoxazolines
Zhengjie He, Hengyu Li, Xun Zhou, Yiyi Liu
The reductive (1 + 4) annulation reaction of isatins and substituted nitroalkenes mediated by a trivalent phosphorus reagent has been realized for the first time, providing easy access to spirooxindolyl isoxazoline N-oxides in moderate to excellent yields with a flexible substrate scope. This reaction presumably proceeds through a Michael addition–intramolecular substitution sequence via active in situ generated Kukhtin–Ramirez zwitterions from isatins and P(NMe2)3. It is also demonstrated that the spirooxindolyl isoxazoline N-oxides can be readily converted into the corresponding isoxazolines in good yields.

Publisher URL: http://dx.doi.org/10.1021/acs.joc.7b01962

DOI: 10.1021/acs.joc.7b01962

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