Substitution and cyclization reactions involving the quasi-antiaromatic 2H-indol-2-one ring system.
The quasi-antiaromatic 2H-indol-2-one ring system is readily generated by treating a 3-hydroxy-substituted 1,3-dihydroindol-2-one with a Lewis acid. Stepwise addition of various pi-nucleophiles to the highly reactive 2H-indol-2-one system occurs smoothly to afford substituted oxindoles. The cyclization was also carried out in an intramolecular fashion to give spiro-substituted oxindoles in good yield.
England
Dylan B
DB
Department of Chemistry, Emory University, Atlanta, Georgia 30322.
Merey
Gokce
G
Padwa
Albert
A
D003500:Cyclization; D007211:Indoles / Q000138:chemical synthesis / Q000737:chemistry*; D047028:Macrocyclic Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure
D007211:Indoles; D047028:Macrocyclic Compounds