Issue 81, 2024

Radical relay strategy for the construction of alkylsulfonated indolo[2,1-a]isoquinoline-6(5H)-ones via SO2 insertion/Smiles rearrangement

Abstract

A new radical relay approach for the efficient construction of alkylsulfonated indolo[2,1-a]isoquinoline-6(5H)-ones in moderate to good yields under mild conditions via SO2 insertion/Smiles rearrangement/intramolecular cyclization is developed. This approach utilizes 4-alkyl substituted Hantzsch esters as alkyl radical sources and further undergoes in situ SO2 insertion to obtain alkylsulfonyl radical species, which avoids the use of unstable alkyl sulfonyl chlorides and highly toxic sulfonyl hydrazides. Additionally, this method for the direct assembly of alkylsulfonated polycyclic molecule skeletons displays high chemical selectivity, broad substrate scope, and step-economy.

Graphical abstract: Radical relay strategy for the construction of alkylsulfonated indolo[2,1-a]isoquinoline-6(5H)-ones via SO2 insertion/Smiles rearrangement

Supplementary files

Article information

Article type
Communication
Submitted
02 Aug 2024
Accepted
14 Sep 2024
First published
24 Sep 2024

Chem. Commun., 2024,60, 11568-11571

Radical relay strategy for the construction of alkylsulfonated indolo[2,1-a]isoquinoline-6(5H)-ones via SO2 insertion/Smiles rearrangement

S. Tian, L. Zhong, J. Fan, K. Tang and Y. Liu, Chem. Commun., 2024, 60, 11568 DOI: 10.1039/D4CC03924F

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