Assembly of Furazan-Fused Quinolines via an Expeditious Metal-Free [2+2+1] Radical Tandem Cyclization Process

A [2+2+1]-NO-segment-incorporating heteroannulative cascade is described. This versatile method, particularly using modular cyanoarylated ketimine substrates, allows efficient access to structurally diversified quinolines embedded with an oxadiazole core. This metal-free protocol proceeds smoothly at 30 degrees C, offers easy manipulation of substituents on the quinoline moiety, and tolerates a spectrum of functional groups. Density functional theory calculation revealed that the cyano moiety is crucial to facilitate the early cyclization step in this heteroannulation process and is different from the previously established late cyclization mechanistic interpretation.

Automated summary

This study presents an efficient method for accessing structurally diversified quinolines through a metal-free cascade reaction at 30 degrees C, offering easy manipulation of substituents. Density functional theory calculations suggest that the cyano moiety plays a crucial role in facilitating the early cyclization step in this heteroannulation process.