Chemical and Pharmaceutical Bulletin
Online ISSN : 1347-5223
Print ISSN : 0009-2363
ISSN-L : 0009-2363
Pummerer-Type Reaction of α-Acylsulfides Using Phenyl Iodosyl Bis(trifluoroacetate)
田村 恭光矢倉 隆之城内 善昭春田 純一
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キーワード: α-methoxylation
ジャーナル フリー

1986 年 34 巻 3 号 p. 1061-1066

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抄録
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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© The Pharmaceutical Society of Japan
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