Schiff Bases as External and Internal Electrophiles in Reactions of Functionalized Organolithium Reagents. A New Route to Isoindoline Derivatives and 1,2,3,4-Tetrahydroisoquinolines

Article abstract of DOI:10.1021/jo00315a021

Reaction of Schiff bases with certain functionalized organolithium reagents is useful in the synthesis of 1,2-diarylisoindolines and 2,3-diarylphthalimidines.Schiff bases derived from 2-(2-bromophenyl)ethylamines on halogen-metal exchange with butyllithium undergo a Parham-type cyclization to yield 1-aryl-1,2,3,4-tetrahydroisoquinolines.