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Heating 1‐(2‐ethylsulfinyl)benzoylindole (1) in refluxing p‐xylene [thermal Sulfoxide Electrophilic Sulfenylation (SES)] produces indolo[2,1‐b][1,3]benzothiazin‐12‐one (2) in 66% yield. Similar treatment of 1‐methyl‐3‐(2‐ethylsulfinyl)benzoylindole (8) provides three products: sulfide 7 and cyclized products 9 and 10 in 10, 19 and 15% yield, respectively. Conversion of 10 to 9 under the reaction conditions is demonstrated and a spirocyclic intermediate 12, which may form from both 9 and 10 but undergoes only preferential S‐migration, is postulated to account for the rearrangement.
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Bates et al. (1995) studied this question.
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