Issue 18, 2021

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.

Graphical abstract: 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

Supplementary files

Article information

Article type
Paper
Submitted
25 Feb 2021
Accepted
05 Apr 2021
First published
06 Apr 2021

New J. Chem., 2021,45, 8314-8320

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

L. Pan, Q. Wang, J. Sun, Q. Sun and C. Yan, New J. Chem., 2021, 45, 8314 DOI: 10.1039/D1NJ00947H

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