Synthesis of Fused Carbazoles by Gold-Catalyzed Tricyclization of Conjugated Diynes via Rearrangement of an N-Propargyl Group

Access this Article

Abstract

Various N-propargylanilines bearing a conjugated diyne moiety at the 2-position were converted to tetracyclic fused carbazoles by treatment with a homogeneous gold(I) catalyst. This cascade reaction proceeds through indole formation with concomitant rearrangement of the N-propargyl group, intramolecular nucleophilic addition toward the resulting allene moiety, and subsequent hydroalkenylation. This transformation enables a one-pot synthesis of fused carbazoles from readily accessible substrates with 100% atom economy.

Journal

  • Organic Letters

    Organic Letters 17(24), 6250-6253, 2015-12-18

    American Chemical Society

Codes

  • NII Article ID (NAID)
    120006634626
  • Text Lang
    ENG
  • Article Type
    journal article
  • ISSN
    1523-7060
  • Data Source
    IR 
Page Top