Synthesis of Ester-Substituted Polycyclic N-Heteroaromatics via Photocatalyzed Alkoxycarbonylation/Tricyclization Reactions of Enediyne in Continuous Flow Conditions

The Journal of Organic Chemistry, Journal Year: 2025, Volume and Issue: unknown

Published: March 20, 2025

For the first time, a photoredox-catalyzed alkoxycarbonylation/tricyclization reaction was developed by employing readily accessible enediynes and alkyloxalyl chlorides as starting materials, enabling synthesis of ester-substituted polycyclic N-heteroaromatics under mild conditions through radical-mediated mechanism. This photocatalytic strategy is notable for its exceptional compatibility with diverse functional groups, scalability, efficiency in formation rings chemical bonds. Notably, continuous flow photocatalysis technology markedly improved these reactions compared to equivalent batch reactions, efficiently decreasing times merely 40 min.

Language: Английский

Photoredox/HAT-Catalyzed Intramolecular Hydrocyclization of Alkenes toward 2,3-Fused Quinazolinones and Dihydroquinazolinones

Organic Letters, Journal Year: 2024, Volume and Issue: unknown

Published: Oct. 2, 2024

New photochemical approaches to 2,3-fused quinazolinones and dihydroquinazolinones are disclosed. The intramolecular hydrocyclization proceeds in moderate excellent yields across diverse alkenes with high regioselectivity diastereocontrol. Mechanistic studies indicated that the radical cascade processes involve thiophenol acting as single-electron transfer hydrogen atom reagents. success of gram-scale synthesis proves strategy can be used for practical applications.

Language: Английский