Molecular diversity of the acid promoted domino reaction of 3-hydroxy-3-(indol-3-yl)indolin-2-ones and cyclic mercapto-substituted β-enamino esters

Abstract

The acetic acid promoted reaction of 3-hydroxy-3-(indol-3-yl)indolin-2-ones and mercapto-substituted β-enamino esters showed very interesting molecular diversity. The reaction in ethanol at room temperature in the presence of acetic acid resulted in two diastereoisomeric 3,3-disubstituted oxindoles in high yields. When the reaction was carried out in refluxing ethanol, the reaction with 3-hydroxy-3-(indol-3-yl)indolin-2-ones with N-alkyl groups gave polycyclic spirooxindoles in satisfactory yields. However, a similar reaction with 3-hydroxy-3-(indol-3-yl)indolin-2-ones with NH groups afforded functionalized dihydroindolo[3,2-c]phenothiazines with sequential ring-opening of oxindole. A plausible domino annulation mechanism was rationally proposed for the formation of different kinds of polycyclic compounds.