Carbinolamine Equivalents in the 8-Amino-tetrahydroisoquinoline Series

Article abstract of DOI:10.1002/ardp.19883210510

Hg(II)-EDTA dehydrogenations of the 8-aminosubstituted tetrahydroisoquinolines 1 and 2 do not yield the expected pure carbinolamines, but the dimers 7 and 8 in an intermolecular reaction.The acetylation of the dimers or of the corresponding iminium salts 5 and 6, respectively, generates the tricyclic primary products 9 and 13, which show ring cleavage when the reaction time is prolongated.