Issue 25, 2023

Metal- and additive-free radical-triggered nitration/cyclization to construct indolo[2,1-α]isoquinoline and benzimidazo[2,1-a]isoquinolin-6(5H)-one derivatives using t-BuONO as nitro reagents

Abstract

An efficient metal- and additive-free nitro radical-triggered addition/cyclization of 2-aryl-N-acryloyl indoles/2-arylbenzimidazoles for the synthesis of nitro-substituted indolo[2,1-α]isoquinoline and benzimidazo[2,1-a]isoquinolin-6(5H)-one derivatives has been developed. The commercially available and low-cost t-BuONO was used as a nitro reagent. Due to mild reaction conditions, a variety of functional groups could be tolerated to give the corresponding products in moderate to good yields. Moreover, this nitration process could be scaled-up and the nitro group could be readily converted into the amino group, which may find applications in synthetic and medicinal chemistry.

Graphical abstract: Metal- and additive-free radical-triggered nitration/cyclization to construct indolo[2,1-α]isoquinoline and benzimidazo[2,1-a]isoquinolin-6(5H)-one derivatives using t-BuONO as nitro reagents

Supplementary files

Article information

Article type
Paper
Submitted
23 Apr 2023
Accepted
06 Jun 2023
First published
07 Jun 2023

Org. Biomol. Chem., 2023,21, 5254-5264

Metal- and additive-free radical-triggered nitration/cyclization to construct indolo[2,1-α]isoquinoline and benzimidazo[2,1-a]isoquinolin-6(5H)-one derivatives using t-BuONO as nitro reagents

Y. Tang, Y. Yang, Q. Zhou, J. Duan, B. Yang, C. Du and Y. He, Org. Biomol. Chem., 2023, 21, 5254 DOI: 10.1039/D3OB00630A

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