The coupling-isomerization approach to enimines and the first sequential three-component access to 2-ethoxy pyridines

The coupling-isomerization reaction (CIR) of electron-deficient halides 1 with N-[1-(hetero)arytprop-2-ynyl] tosyl amides 2 leads to the formation of N-tosyl enimines 3, in good to excellent yields. These electron deficient heterodienes are perfectly suited for Diels-Alder reactions with inverse electron demand. In the sense of a one-pot reaction a three-component CIR-cyclocondensation sequence of 1, 2a, and diethyl ketene acetal gives rise to the formation of 2-ethoxy 6-(p-anisyl)pyridines 4 in moderate to good yields.