Isatin, a natural product obtained from plants, such as isatis tinctoria and calanthe discolor, possesses important bioactive response which could be potentially used as antimicrobial, chemotherapeutic agents, inhibitors of diaminopimelate aminotransferase and kinase 2. Recently, we have demonstrated that ?-lactams C  can be prepared from a one-pot three-component reaction through initial phosphines nucleophilic attack at the a(d')-carbon of enyne A  to generate reactive zwitterions followed by addition to electron-deficient aldimines B  . Our interests in building up isatin core structure through this developed approaches led us to evaluate reactivity of cinnamaldimines for building up structure D  . The structure D  can be transformed to isatin derivatives F   through [2+2+2] electrocyclization and oxidation. Further oxidation of isatin derivatives F  with mCPBA provided unexpected compounds isoxazolinones G  . In this presentation, the condition optimization and reaction scope of this developed approach toward syntheses of isatin derivatives and isoxazolinones will be discussed. These results are supported by unambiguous characterization with NMR, FT-IR, HRMS and X-ray diffraction analysis. 

Isatin derivatives and isoxazolinones from tandem anti-Michael three-component assembly and oxidation

248th National Meeting (2014)

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