Abstract
A novel method for the synthesis of 3-monohalooxindoles by acidolysis of isatin-derived 3-phosphate-substituted oxindoles with haloid acids was developed. This synthetic strategy involved the preparation of 3-phosphate-substituted oxindole intermediates and SN1 reactions with haloid acids. This new procedure features mild reaction conditions, simple operation, good yield, readily available and inexpensive starting materials, and gram-scalability.
Highlights
A novel method for the synthesis of 3-monohalooxindoles by acidolysis of isatin-derived 3-phosphate-substituted oxindoles with haloid acids was developed
During the exploratory study of this work, we chose concentrated hydrochloric acid (36%) as the readily available chlorinating reagent to screen the reaction conditions, and we carried out our initial synthetic reaction with diethyl (2-oxoindolin-3yl) phosphate (2a) under solvent-free and catalyst-free conditions at room temperature (Table 1, entry 1)
We evaluated the effect of the reaction time on the acidolysis reaction
Summary
A novel method for the synthesis of 3-monohalooxindoles by acidolysis of isatin-derived 3-phosphate-substituted oxindoles with haloid acids was developed. During the exploratory study of this work, we chose concentrated hydrochloric acid (36%) as the readily available chlorinating reagent to screen the reaction conditions, and we carried out our initial synthetic reaction with diethyl (2-oxoindolin-3yl) phosphate (2a) under solvent-free and catalyst-free conditions at room temperature (Table 1, entry 1). We examined the substrate scope of this transformation between hydrochloric acid (36%) with various substituted (2-oxoindolin-3-yl) phosphates 2.
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