Studies concerning partially reduced nitrogen heterocycles

Carbanion rearrangement studies on selected N-acyl-isoquinoline and -quinoline Reissert compounds have shown that alternative intramolecular rearrangements can compete successfully with the normal 1,2-acyl-migration. The observations have been rationalised mechanistically and their potential value in synthesis demonstrated. In particular the formation of a 1-benzoyl-8-hydroxyisoquinoline derivative has been effected from carbanion rearrangement of the corresponding 8-benzoyloxy Reissert compound. N-Crotonoylisoquinoline Reissert compound carbanion and analogous structures have been shown to undergo a complex reaction in which Michael type attack competes with the normal migration. [Continues.]