Abstract
The oxidation of 3-heteroarylindoles to the corresponding 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.
Key words
indole - oxindole -
t -BuOCl - oxidation - heterocycles
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