Abstract
A series of functionalized spiro[indoline-3,2'-oxiran]-2-ones was efficiently synthesized by Darzens reaction of phenacyl bromides with isatins both with N-alkyl groups and without N-substituent in the presence of potassium carbonate as a base catalyst. When two equivalents phenacyl bromides were used in the reaction, the N-substitution reaction of isatin also finished with the formation of spiro-oxirane-oxindoles.
Highlights
The spirooxindole unit is a privileged heterocyclic motif that forms the core structure of a large family of natural alkaloids and many pharmacological agents with important bioactivity and interesting structural properties [1-5]
We envisaged that in situ generated pyridinium ylide might react with the reactive carbonyl group of isatins to afford spiro epoxyoxindoles (Scheme 1)
Our attention was turned toward the development of straightforward reactions of phenacyl bromides with isatins
Summary
The spirooxindole unit is a privileged heterocyclic motif that forms the core structure of a large family of natural alkaloids and many pharmacological agents with important bioactivity and interesting structural properties [1-5]. With the aim of expanding our previous studies on the synthesis of various spirooxindoles [20-25], we decided to systematically investigate the Darzens reactions of a series of isatins with phenacyl bromides and report the facile synthesis of versatile spiro[indoline-3,2'oxiran]-2-ones.
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