Synthesis of trans/cis-3,4-disubstituted 1,2,3,4-tetrahydroisoquinolines by nucleophilic acyl substitution of homophthalic anhydride with aldimines

摘要

The reaction of the functionalized N-protected imines 3 and 7 containing either the chloromethyl or ethyl ester moieties, respectively, attached to the imine carbon with homophthalic anhydride 2 afforded cis/tran-3-subsituted-1-oxo- 1,2,3,4-tetrahydroisoquinoline-4-caboxylic acids appropriate for further synthetic elaboration.