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  • Title: Catalytic stereoselective synthesis of diverse oxindoles and spirooxindoles from isatins.
    Author: MacDonald JP, Badillo JJ, Arevalo GE, Silva-García A, Franz AK.
    Journal: ACS Comb Sci; 2012 Apr 09; 14(4):285-93. PubMed ID: 22449252.
    Abstract:
    A strategy for the efficient two-step synthesis of triazole derivatives of oxindoles and spirooxindoles is presented. Using a common set of N-propargylated isatins, a series of mechanistically distinct stereoselective reactions with different combinations of nucleophiles and catalysts provide access to diverse hydroxy-oxindoles, spiroindolones, and spirocyclic oxazoline structures. The resulting N-propargylated oxindoles are then converted to triazoles using copper-catalyzed azide-alkyne cycloaddition (CuAAC) reactions. Overall, this strategy affords a 64-member pilot-scale library of diverse oxindoles and spirooxindoles.
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