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Catalytic stereoselective synthesis of diverse oxindoles and spirooxindoles from isatins.

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.

SUBMITTER: MacDonald JP

PROVIDER: S-EPMC4795923 | biostudies-literature | 2012 Apr

REPOSITORIES: biostudies-literature

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Catalytic stereoselective synthesis of diverse oxindoles and spirooxindoles from isatins.

MacDonald Jacob P JP Badillo Joseph J JJ Arevalo Gary E GE Silva-García Abel A Franz Annaliese K AK

ACS combinatorial science 20120402 4

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 cycload ...[more]

PMID: 22449252

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