Chemo- and Regioselective Imino Diels-Alder Reactions: Synthesis of Functionalized Novel Quinolin-3-one and Quinoline Derivatives

Regio-and catalyst selective imino Diels-Alder reactions of vinyl/isopropenyl pyrimidinones with N-arylimines in the presence of metal salts viz.magnesium(II) bromide, zinc(II) chloride, indium(III) chloride, yttrium triflate and scandium triflate, are described.An unprecedented oxidation of methylene to carbonyl has been shown to accompany the imino Diels-Alder reactions of isopropenyl pyrimidinones in the presence of yttrium and scandium triflates.Chemoselective effect of different Lewis acids used as catalysts in these reactions has been rationalized.