Utilization of the antiaromatic 2H-indol-2-one ring system for the synthesis of substituted spiro-oxindoles

England D. B., Merey G., Padwa A.

HETEROCYCLES, cilt.74, ss.491-506, 2007 (SCI-Expanded) identifier identifier

  • Yayın Türü: Makale / Tam Makale
  • Cilt numarası: 74
  • Basım Tarihi: 2007
  • Dergi Adı: HETEROCYCLES
  • Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Sayfa Sayıları: ss.491-506
  • Marmara Üniversitesi Adresli: Hayır

Özet

The utility of the quasi-antiaromatic 2H-indol-2-one system for the synthesis of substituted oxindoles and spiro-oxindoles was investigated. The highly reactive 2H-indol-2-one could be readily generated by treating a 3-hydroxy substituted 1,3-dihydroindol-2-one with a Lewis acid. Stepwise addition of various a-substrates such as styrene, furan and thiophene to the 2H-indol-2-one system occurs smoothly to produce a carbocation intermediate which subsequently undergoes proton loss to afford substituted oxindoles. The cyclization was also carried out in an intramolecular fashion to give spiro-substituted oxindoles in good yield.