Issue 17, 2024
From the journal:

Organic & Biomolecular Chemistry

HFIP-mediated C-3-alkylation of indoles and synthesis of indolo[2,3-b]quinolines & related natural products†

Auqib Rashid,abc   Waseem I. Lone,‡bc   Preeti Dogra,‡b   Showkat Rashid ORCID logo *bc  and  Bilal A. Bhat ORCID logo *ac  

* Corresponding authors

a Natural Products & Medicinal Chemistry Division, CSIR-Indian Institute of Integrative Medicine, Sanatnagar, Srinagar 190005, India
E-mail: bilal@iiim.res.in

b Natural Products & Medicinal Chemistry Division, CSIR-Indian Institute of Integrative Medicine Jammu, Jammu and Kashmir 180001, India
E-mail: showkat.rashid@iiim.res.in

c Academy of Scientific and Innovative Research (AcSIR), Ghaziabad 201002, India

Abstract

An expeditious metal free C-3 alkylation of indoles and its NIS-mediated deviation to indolo[2,3-b]quinolines is reported. This protocol, executed in aqueous HFIP has broad substrate scope and is well inclined towards the ideas of sustainable chemistry. Applications of these strategies in accessing bioactive natural products like vibrindole, norcryptotakeine, neocryptolepine and indenoindolone scaffolds has also been demonstrated.

Graphical abstract: HFIP-mediated C-3-alkylation of indoles and synthesis of indolo[2,3-b]quinolines & related natural products

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Article information

DOI
https://doi.org/10.1039/D4OB00414K
Article type
Paper
Submitted
14 Mar 2024
Accepted
04 Apr 2024
First published
05 Apr 2024

Org. Biomol. Chem., 2024,22, 3502-3509

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HFIP-mediated C-3-alkylation of indoles and synthesis of indolo[2,3-b]quinolines & related natural products

A. Rashid, W. I. Lone, P. Dogra, S. Rashid and B. A. Bhat, Org. Biomol. Chem., 2024, 22, 3502 DOI: 10.1039/D4OB00414K

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