Synthesis of Fused Carbazoles by Gold-Catalyzed Tricyclization of Conjugated Diynes via Rearrangement of an N -Propargyl Group
Year: 2015
Type: 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.
Source: Organic Letters
Institution: Kyoto University
Language: English
Topic: Catalytic Alkyne Reactions
Subfield: Organic Chemistry
Field: Chemistry
Domain: Physical Sciences
Open Access status: hybrid
Estimated APC paid: $4,500
Awards: Development of Novel Drug Discovery Technologies for Target Proteins with Elusive Molecular Basis, Precise activation based on transition state control using neighboring effect and its medicinal application, Innovative Molecular Transformations Based on Consecutive pai-Activation and Their Medicinal Applications
OpenAlex ID: W2400611782