Issue 44, 2023

Skeletal rearrangement through photocatalytic denitrogenation: access to C-3 aminoquinolin-2(1H)-ones

Abstract

The addition of an amine group to a heteroaromatic system is a challenging synthetic process, yet it is an essential one in the development of many bioactive molecules. Here, we report an alternative method for the synthesis of 3-amino quinolin-2(1H)-one that overcomes the limitations of traditional methods by editing the molecular skeleton via a cascade C–N bond formation and denitrogenation process. We used TMSN3 as an aminating agent and a wide variety of 3-ylideneoxindoles as synthetic precursors for the quinolin-2(1H)-one backbone, which demonstrates remarkable tolerance of sensitive functional groups. The control experiments showed that the triazoline intermediate plays a significant role in the formation of the product. The spectroscopic investigation further defined the potential reaction pathways.

Graphical abstract: Skeletal rearrangement through photocatalytic denitrogenation: access to C-3 aminoquinolin-2(1H)-ones

Supplementary files

Article information

Article type
Edge Article
Submitted
24 Aug. 2023
Accepted
13 Okt. 2023
First published
17 Okt. 2023
This article is Open Access

All publication charges for this article have been paid for by the Royal Society of Chemistry
Creative Commons BY-NC license

Chem. Sci., 2023,14, 12541-12547

Skeletal rearrangement through photocatalytic denitrogenation: access to C-3 aminoquinolin-2(1H)-ones

S. Singh, G. Chakrabortty and S. Raha Roy, Chem. Sci., 2023, 14, 12541 DOI: 10.1039/D3SC04447E

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