Photoredox One-Pot Synthesis of 3,4-Dihydroquinolin-2(1H)-ones

Abstract

A photoredox one-pot strategy for efficient accessing 3,4-dihydroquinolin-2(1H)-ones from anilines, oxalyl chloride, and electron-deficient alkenes is disclosed. The new approach features excellent synthetic efficiency, readily available starting materials, and simple operations. It is compatible with a variety of anilines and electron-deficient alkenes. A broad array of 3,4-dihydroquinolin-2(1H)-ones were prepared.

Recent Advances for the Synthesis of Dihydroquinolin-2(1H)-ones via Catalytic Annulation of α,β-Unsaturated N-Arylamides

“…The importance of this skeleton compound has stimulated activities of the synthesis community to develop new transformation strategies that can obtain DHQO compounds. In the past decades, some new synthetic methods have been continuously developed, such as the Pd-catalyzed Heck reduction-cyclization reaction [7], Pd-catalyzed cyclopropane ring expansion [8], Mn-mediated intramolecular cyclization [9], Rh-mediated Michaeladdition (1,4-additions) of the boronic acid to enone [10], Ru catalyzed cyclization of 1,4,2-dioxazol-5-ones [11], photoredox strategy from anilines, oxalyl chloride and electrondeficient alkenes [12], and so on [13][14][15][16][17][18][19]. Among these, using α,β-unsaturated N-arylamides as the key substrates via different cyclization reactions has been shown as a fast, simple, and atom-economic strategy.…”