A Facile Method for the Synthesis of 3-Substituted 3-(Alkylthio)oxindoles or 3-Alkoxyoxindoles

Abstract

We report a highly efficient perchloric acid catalyzed substitution reaction of 3-hydroxyoxindoles with thiols and alcohols for the synthesis of 3-substituted 3-(alkylthio)oxindoles or 3-alkoxyoxindoles, with catalyst loading down to 0.5 mol%. The scope and limitation of this method has been studied. An unprecedented mercury(II) perchlorate trihydrate catalyzed tandem Sakurai­–Hosomi/(thio)ether formation reaction, starting from isatins, allyltrimethylsilane, and thiols or alcohols, has also been developed, which enables the facile synthesis of versatile 3-(alkylthio)- or 3-alkoxy-3-allyloxindoles.

Key words

3-hydroxyoxindoles - 3-(alkylthio)oxindoles - 3-alkoxy­oxindoles - tandem reaction - atom-efficient

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