Enamine chemistry. Part XI. Reaction of αβ-unsaturated acids and acid chlorides with imines. Synthesis of 2-oxotetrahydropyridines and 2-oxo-octahydroquinolines

Abstract

2-Oxotetrahydropyridines and 2-oxo-octahydroquinolines have been isolated from the reaction of acryloyl chloride with imines, together with the enamide and, in some cases, the amide. Crotonoyl and cinnamoyl chlorides give mixtures consisting mainly of the enamides. 2-Oxotetrahydropyridines and 2-oxo-octahydroquinolines have also been isolated from the reaction of acrylic acid with imines. The mechanisms of these reactions are discussed.