NaHS·nH2O-induced umpolung: the synthesis of 2-acyl-3-aminoindoles from aryl methyl ketones and 2-aminobenzonitriles

Xiao Geng; Xia Wu; Can Wang; Peng Zhao; You Zhou; Xuan Sun; Ling-Jiao Wang; Wen-Juan Guan; Yan-Dong Wu; An-Xin Wu

doi:10.1039/C8CC07599A

NaHS·nH₂O-induced umpolung: the synthesis of 2-acyl-3-aminoindoles from aryl methyl ketones and 2-aminobenzonitriles†

Xiao Geng,‡^a Xia Wu,‡^a Can Wang,^a Peng Zhao,^a You Zhou,^a Xuan Sun,^a Ling-Jiao Wang,^a Wen-Juan Guan,^a Yan-Dong Wu*^a and An-Xin Wu

*^a

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^a Key Laboratory of Pesticide & Chemical Biology, Ministry of Education, College of Chemistry, Central China Normal University, Wuhan 430079, P. R. China
E-mail: chwuyd@mail.ccnu.edu.cn, chwuax@mail.ccnu.edu.cn

Abstract

An efficient method for constructing 2-acyl-3-aminoindoles from methyl ketones and 2-aminobenzonitriles is described, in which NaHS·nH₂O is used as a novel umpolung reagent for the first time in organic synthesis. Mechanistic studies revealed that the key step involved an Eschenmoser sulfide contraction reaction.

Chemical Communications

NaHS·nH₂O-induced umpolung: the synthesis of 2-acyl-3-aminoindoles from aryl methyl ketones and 2-aminobenzonitriles†

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NaHS·nH₂O-induced umpolung: the synthesis of 2-acyl-3-aminoindoles from aryl methyl ketones and 2-aminobenzonitriles

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