Abstract
In order to introduce 2-pyridyl group into the 9 position of 1, 1-disubstituted quinolizidine, N-benzoyloxypyridinium chloride (1) was treated with 9-dehydro-1-oxoquinolizidine (3), dehydro-1-ethoxycarbonyl-1-hydroxyquinolizidine (13) and 9-dehydro-1, 1-ethylenedioxyquinolizidine (16) in dichloromethane, followed by reduction of the reactants with sodium borohydride in anhyd. ethanol. Although reactions with 3 and 13 gave no satisfactory result, that with 16 afforded the expected 1, 1-ethylenedioxy-9-(2-pyridyl)-quinolizidine (18) in 17% yield together with dehydro-1, 1-ethylenedioxy-x-(2-pyridyl)-quinolizidine (19). Other observations encountered in reactions of 1 with 3 or 13 as well as in transformation of 2 into 13 and 16 were also described in some detail.
