Abstract
2-Nitro-1-(phenylsulfonyl)indole ( 1) undergoes nucleophilic addition reactions with the enolates of diethyl malonate and cyclohexanone, lithium dimethylcuprate, and indole anion to afford the corresponding 3-substituted-2-nitroindoles ( 4–6, 8, 9) in low to high yields. Reaction of 1-(phenylsulfonyl)-2-(trialkylstannyl)indoles 13 and 14 with tetranitromethane affords the novel isoxazolo[5,4- b]indole 15 via a 1,3-dipolar cycloaddition reaction with in situ generated nitro formonitrile oxide ( 19).
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