O -Heterocycles-Fused Indoles via Tandem 1,2-Indole Migration–Hydroxycyclization Reactions in 2-Hydroxyalkyl-3-propargylindoles

Organic Letters 2026 Open access

Read full text
Authors: Lorena Renedo, Marta Solas, Carlos Silva López, Samuel Suárez-Pantiga, Roberto Sanz
DOI: 10.1021/acs.orglett.6c00991
Cited by: 1
References: 51

Abstract

High Resolution Image Download MS PowerPoint Slide Gold(I)-catalyzed tandem cyclization reactions of 3-propargylindoles bearing a hydroxyalkyl substituent at C2 enable rapid access to indole-fused cyclic ethers through the vinylogous reactivity of α,β-unsaturated gold-carbene intermediates. A selective intramolecular Michael-type attack of the hydroxyl group, supported by DFT studies, affords indole-fused six-, seven-, and eight-membered O -heterocycles under mild conditions. A one-pot hydrogen transfer process further delivers reduced pyranoindoles, highlighting the versatility and synthetic potential of this method.

Fields of Study & Subjects

Catalytic Alkyne Reactions Catalytic C–H Functionalization Methods Cyclopropane Reaction Mechanisms

Publication details

Journal / source
Organic Letters
Publisher
American Chemical Society (ACS)
Volume
28
Issue
15
Pages
4922–4927
Publication date
6 April 2026
Language
EN