New Findings on the Vilsmeier-Haack Approach to Quinoline Derivatives

Article abstract of DOI:10.1016/S0040-4020(01)80253-2

The presence of electron-releasing substituents on the aromatic ring of anilides, although necessary for the Vilsmeier-Haack cyclization to quinolines to proceed efficiently, can cause failure of the expected cyclization, leading to (Z) N,N-dimethylformamidines through an alternative course.A similar behaviour is observed when ?-donor groups are introduced on the α position of the anilide, although in this case some cyclization to quinoline derivatives generally occurs.