Pyridines and pyridine derivatives from vinyl allenes and imines

Abstract

The Lewis acid mediated reaction of acyclic vinyl allenes and imines, yielding tetrahydropyridines has been carried out. Only one cycloadduct was observed in each case, and thus, the reaction progressed in all cases with total regio-, face- and endo/exo selectivities. The cycloadducts were transformed into polysubstituted pyridines, including bipyridines, by catalytic transfer hydrogenation using cyclohexene as hydrogen donor in good yield. The reaction was extended to the aromatization of the bicyclic cycloadducts prepared in previous works from the reaction of semicyclic vinyl allenes and imines, yielding tetrahydropyridines.