title: 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.
authors.affiliation: Department of Chemistry, University of California, Davis, California 95616, United States.
authors.forename: Jacob P
authors.initials: JP
authors.lastname: MacDonald
authors.forename: Joseph J
authors.initials: JJ
authors.lastname: Badillo
authors.forename: Gary E
authors.initials: GE
authors.lastname: Arevalo
authors.forename: Abel
authors.initials: A
authors.lastname: Silva-García
authors.forename: Annaliese K
authors.initials: AK
authors.lastname: Franz
mesh_terms: D000480:Alkynes / Q000737:chemistry; D001386:Azides / Q000737:chemistry; D002384:Catalysis; D020650:Combinatorial Chemistry Techniques; D003300:Copper / Q000737:chemistry*; D003500:Cyclization; D007211:Indoles / Q000138:chemical synthesis* / Q000737:chemistry; D007510:Isatin / Q000737:chemistry*; D015394:Molecular Structure; D000078183:Oxindoles; D013141:Spiro Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D000480:Alkynes; D001386:Azides; D007211:Indoles; D000078183:Oxindoles; D013141:Spiro Compounds; C022960:2-oxindole; D003300:Copper; D007510:Isatin