Abstract
Radul et al. recently reported [1] on the N-alkylation of unsubstituted and sybstituted isatins with a-bromo ketones in benzene and toluene in the presence of bases (pyridine, triethylamine, K2CO3). These reactions led to formation of the corresponding N-acetonyland N-phenacylisatins which are used as starting compounds in the dihydroindoledione3indole rearrangement. A disadvantage of the proposed procedure is poor solubility of initial isatins in the above solvents. In addition, high reactivity of the carbonyl group in the b-position and ready generation of anions from bromo ketones by the action of bases favor the Darzens condensation, and separation of the products by preparative thin-layer chromatography is difficult because of their similar mobilities in different solvent systems.
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