Visible‐Light‐Induced Benzylic C‐H Functionalization for the Synthesis of 2‐Arylquinazolines

Abstract

This work reports a mild and efficient approach for the synthesis of substituted quinazolines using 1‐(2‐aminoaryl)ethan‐1‐ones in conjunction with arylmethanamines as starting materials via visible‐light‐induced benzylic C–H functionalization. The reaction proceeded at room temperature with low catalyst loading and the reaction system was clean from beginning to end. Significantly, this method exhibited good tolerance even to free hydroxyl group and amino group contained in substrates.

Visible‐Light‐Driven Cyclizations

“…In 2019, Shi reported a visible light-promoted reaction for the synthesis of quinazolines 646 using benzyl amines 641 and 2-amino benzaldehyde or benzoketone derivatives 644 and as starting materials. [188] The proposed mechanism starts with the photocatalytic excitation of the Ir(ppy) 3 catalyst VII by visible light. The excited complex is oxidized via a SET process with tert-butyl peroxybenzoate (TBPB) to generate the tert-butoxy radical and the Ir IV complex.…”

“…In 2019, Shi reported a visible light‐promoted reaction for the synthesis of quinazolines 646 using benzyl amines 641 and 2‐amino benzaldehyde or benzoketone derivatives 644 and as starting materials [188] . The proposed mechanism starts with the photocatalytic excitation of the Ir(ppy) 3 catalyst VII by visible light.…”

A TEMPO promoted tandem reaction of 2-aminobenzophenones and benzylamines under electrochemical conditions

“…10 Zhang and co-workers reported the visible light induced benzyl C–H functionalized synthesis of quinazolines under mild conditions (Scheme 1b). 11 Shen and co-workers reported the efficient synthesis of quinazolines under photo-redox conditions with common N -alkyl- N ‘-aryl species (Scheme 1c). 12 Liu and co-workers developed an efficient synthesis of quinazoline derivatives by using 2,1-benzodiazole and α-azidone as substrates (Scheme 1d).…”

Copper‐Catalyzed Acceptorless Dehydrogenative Coupling of 2‐Aminoaryl Methanols with Nitriles for Accessing Quinazolines and Quinolines

“…Due to the high medicinal value of quinazoline derivatives, development of new synthetic strategies still seems to be an attractive field of research. There are several synthetic approaches developed for the synthesis of quinazolines, [10a–f] among them one of the most recent methods is the acceptorless dehydrogenative coupling (ADC) of 2‐aminoaryl methanols with different nitriles. A significant development has been observed in the synthesis of quinazoline derivatives using this technique.…”