Indoloquinazolines functionalized at C-12, which are structural analogs of the natural
alkaloid cephalanthrin B, are readily constructed via Ph3P/I2-mediated one-pot reactions of isatins with aromatic alcohols. In the presence of
excess phenols, the C-12 aryloxy ester products are obtained in moderate to good yields
under mild conditions. Moreover, fused bicyclic hydroxyaryl derivatives such as 8-hydroxyquinoline
give rise to novel C-12 spiro-γ-lactone derivatives. A reactive iminium cation species
derived from dehydration of the C-12 hydroxy ester precursor is proposed as the transient
intermediate responsible for these transformations.
Key words
indoloquinazolines - isatin - triphenylphosphine - iodine - spirolactones - condensation
