Issue 29, 2022

Synthesis of ester-functionalized indolo[2,1-a]isoquinolines via iron-catalyzed radical cascade cyclization of 2-aryl-N-acryloyl indoles with carbazates

Abstract

An FeCl2·4H2O-catalyzed oxidative alkoxycarbonylation/cyclization reaction of 2-aryl-N-acryloyl indoles with carbazates leading to ester-functionalized indolo[2,1-a]isoquinoline derivatives has been developed. The reaction features mild reaction conditions and broad functional group tolerance. Moreover, the ester group could be easily converted to the corresponding free acid and alcohol, and has high potential applications in organic and pharmaceutical synthesis. A radical pathway was proposed to explain this experiment.

Graphical abstract: Synthesis of ester-functionalized indolo[2,1-a]isoquinolines via iron-catalyzed radical cascade cyclization of 2-aryl-N-acryloyl indoles with carbazates

Supplementary files

Article information

Article type
Communication
Submitted
17 May 2022
Accepted
08 Jul 2022
First published
08 Jul 2022

Org. Biomol. Chem., 2022,20, 5704-5711

Synthesis of ester-functionalized indolo[2,1-a]isoquinolines via iron-catalyzed radical cascade cyclization of 2-aryl-N-acryloyl indoles with carbazates

Y. Tang, K. Dai, X. Xiang, Y. Yang and M. Li, Org. Biomol. Chem., 2022, 20, 5704 DOI: 10.1039/D2OB00934J

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