Metal-free One-pot Nenitzescu Synthesis of 5-Hydroxy-[1H]-benzo[g]indole Derivatives
A catalyst-free one-pot synthesis of 5-hydroxy-[1H]-benzo[g]indole derivatives has been developed via a modified Nenitzescu reaction using 1,4-naphthoquinones, β-ketoesters/β-dicarbonyl compounds, and ammonium acetate. The transformation proceeds through in situ enamine formation followed by 5-exo-trig C–N cyclization. The protocol affords diverse 5-hydroxyindoles in good to excellent yields. DFT calculations and TEMPO experiments suggest that the reaction yielded the product via a polar mechanistic pathway.
Authors
- Mrinalkanti Kundu (ORCID: https://orcid.org/0000-0002-0907-6699)
- Sarifuddin Gazi (ORCID: https://orcid.org/0000-0003-4688-7383)
- Krishnendu Khamaru (ORCID: https://orcid.org/0000-0002-9178-2794)
- Sarajit Naskar
- Md Ashif Ali (ORCID: https://orcid.org/0009-0005-6943-3191)
- Pramit Ganguly
- Rajendranath Atta
Institutions
- Indian Institute of Chemical Biology (IN)
- Patliputra University (IN)
- TCG Lifesciences (India) (IN)
- Ramakrishna Mission Residential College (IN)
Publication Details
- Journal
- Synlett
- Published
- 2026-10-31
- DOI
- https://doi.org/10.1055/a-2994-2074
- Primary Topic
- Synthesis of Indole Derivatives
- Type
- article
- Field-Weighted Citation Impact
- 0.00