Three-Component Synthesis of 2-Substituted Quinolines and Benzo[f]quinolines Using Tertiary Amines as the Vinyl Source

Abstract

A metal-free method for the construction of 2-substituted quinolines and benzo[f ]quinolines from aromatic amines, aldehydes, and tertiary amines has been demonstrated. Cheap and readily available tertiary amines acted as the vinyl source. A new pyridine ring was selectively formed via [4 + 2] condensation that was promoted by ammonium salt under neutral conditions and an oxygen atmosphere. This strategy provided a new route for the preparation of various quinoline derivatives with different substituents at the pyridine ring, which provides the possibility of further modification.

Synthesis of functionalized quinolines from the cascade reactions of N-aryl amidines with two CF3-ynones via C–H/N–H/C–N/C–C bond cleavage

“…Functionalized quinolines are ubiquitous in natural products, pharmaceuticals, pesticides and fluorescent materials. 1 As another aspect, the introduction of a trifluoromethyl (CF 3 ) unit often exerts a substantial influence on the physicochemical properties, biological activity and metabolic stability of the parent compounds and thus substantially increases the likelihood of lead compound discovery. 2 In this context, CF 3 -substituted quinoline derivatives have demonstrated profound antimalarial, antiviral, antibacterial, anti-inflammatory, antifungal and antiseptic activities.…”