Pummerer-Type Reaction of α-Acylsulfides Using Phenyl Iodosyl Bis(trifluoroacetate)

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Treatment of α-acylsulfides with phenyl iodosyl bis(trifluoroacetate) (PIFA) resulted in a Pummerer-type reaction to give the same products as obtained by the Pummerer reaction of the α-acylsulfoxides. The Pummerer-type reaction of α-acylsulfides using PIFA was applied to Friedel-Crafts type cyclization of N-phenyl-α-(methylthio)acetanilide (1) and ethyl α-(1-phenethylthio)-acetate (9) to give N-phenyl-3-(methylthio)oxindole (3) and ethyl isothiochroman-1-carboxylate (10), respectively, olefin cyclization of α-(methylthio)acetamides (11,13 and 15) to give the lactams (12,14 and 16), and also intermolecular condensation and α-methoxylation of methyl α-(methylthio)acetate (7).

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  • Chem. Pharm. Bull.

    Chem. Pharm. Bull. 34 1061-1066, 1986

    公益社団法人日本薬学会

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