Abstract
The oxidation of 3-heteroarylindoles to the correspond-ing oxindoles with t-butyl hypochlorite has been investigated. Under carefully adjusted conditions, preparative scale of desired products can be achieved. Two competing pathways seem to contribute to the reaction mechanism, affording 3-heteroaryloxindoles bearing hydrogen or chlorine at C3, depending on stereoelectronic factors. The present methodology appears also generally applicable for the preparation of simple 3-aryloxindoles.
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