Issue 47, 2021

Synthesis of indolo[2,1-α]isoquinoline derivatives via metal-free radical cascade cyclization

Abstract

In the present studies, we describe a convenient and efficient protocol for the synthesis of the indolo[2,1-α]isoquinoline core structure through the reaction of 2-aryl-N-acryloyl indoles and aryl or alkyl α-keto acids under air environment in four hours. The developed approach features broad substrate scope and good functional group tolerance under mild reaction conditions without a metal catalyst participation. A series of valuable indolo[2,1-α] isoquinoline derivatives bearing various functional groups were synthesized using this method in good to excellent yields. Based on a series of control experiments, a radical pathway was proposed to explain the experiment.

Graphical abstract: Synthesis of indolo[2,1-α]isoquinoline derivatives via metal-free radical cascade cyclization

Supplementary files

Article information

Article type
Paper
Submitted
28 Sep 2021
Accepted
17 Nov 2021
First published
19 Nov 2021

Org. Biomol. Chem., 2021,19, 10376-10384

Synthesis of indolo[2,1-α]isoquinoline derivatives via metal-free radical cascade cyclization

X. Hu, H. Xu, Q. Chen, Y. Pan and J. Chen, Org. Biomol. Chem., 2021, 19, 10376 DOI: 10.1039/D1OB01917A

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