Studies towards 3,4-Dimethoxy-1-methyl-1,2-dihydropyridine, So-called Arecolidine, or Its Tautomers

Abstract

Different synthetic paths towards the title compound (2) lead to intermediates (3, 11, 13, 14, 15, and 17). All of these, but especially 3 and 14 are very close to the target molecule or its tautomers. These, however, turn out to be too unstable for isolation. Thus, the structure of the compound described as arecolidine must be wrong