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.