A novel four component one-pot access to pyrindines and tetrahydroquinolines

Dihydropyrindines and tetrahydroquinolines, i.e. cyclopentyl and cyclohexyl annealed pyridines, can be synthesized in good yields in a one-pot three-step four-component process by a coupling–isomerization–Stork–enamine alkylation–cyclocondensation sequence of an electron poor (hetero)aryl halide, a terminal propargyl alcohol, a cyclic N-morpholino alkene and ammonium chloride. The structures of the 1,5-diketone 4d and the tetrahydroquinoline 5c were additionally supported by X-ray structure analyses.