title: Domino reactions of vinyl malononitriles with 3-phenacylideneoxindoles for efficient synthesis of functionalized spirocyclic oxindoles.
abstract: The reactions of vinyl malononitriles with 3-phenacylideneoxindoles in ethanol in the presence of DBU as base resulted in the functionalized spirocyclic oxindoles through the domino Michael addition and intramolecular nucleophilic addition to cyano group. On the other hand, the similar reaction in the presence of piperidine as base afforded the simple Michael addition products in good yields. The stereochemistry of the spirooxindoles was established with (1)H NMR data and single crystal structures.
authors.affiliation: College of Chemistry & Chemical Engineering, Yangzhou University , Yangzhou 225002, China.
authors.forename: Ya-Jing
authors.initials: YJ
authors.lastname: Xie
authors.forename: Jing
authors.initials: J
authors.lastname: Sun
authors.forename: Chao-Guo
authors.initials: CG
authors.lastname: Yan
mesh_terms: D007211:Indoles / Q000138:chemical synthesis / Q000737:chemistry*; D008958:Models, Molecular; D015394:Molecular Structure; D009570:Nitriles / Q000737:chemistry*; D000078183:Oxindoles; D013141:Spiro Compounds / Q000138:chemical synthesis* / Q000737:chemistry
chemical_list: D007211:Indoles; D009570:Nitriles; D000078183:Oxindoles; D013141:Spiro Compounds; C022960:2-oxindole; C000945:dicyanmethane