title: Synthesis of Fused Carbazoles by Gold-Catalyzed Tricyclization of Conjugated Diynes via Rearrangement of an N-Propargyl Group.
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.
authors.affiliation: Graduate School of Pharmaceutical Sciences, Kyoto University , Sakyo-ku, Kyoto 606-8501, Japan.
authors.forename: Masamitsu
authors.initials: M
authors.lastname: Taguchi
authors.affiliation: Graduate School of Pharmaceutical Sciences, Kyoto University , Sakyo-ku, Kyoto 606-8501, Japan.
authors.forename: Yusuke
authors.initials: Y
authors.lastname: Tokimizu
authors.affiliation: Graduate School of Pharmaceutical Sciences, Kyoto University , Sakyo-ku, Kyoto 606-8501, Japan.
authors.forename: Shinya
authors.initials: S
authors.lastname: Oishi
authors.affiliation: Graduate School of Pharmaceutical Sciences, Kyoto University , Sakyo-ku, Kyoto 606-8501, Japan.
authors.forename: Nobutaka
authors.initials: N
authors.lastname: Fujii
authors.affiliation: Graduate School of Pharmaceutical Sciences, Kyoto University , Sakyo-ku, Kyoto 606-8501, Japan.
authors.forename: Hiroaki
authors.initials: H
authors.lastname: Ohno