An organosilicon route to the B-norbenzomorphan skeleton

Abstract

Organosilicon compounds are receiving increased attention on account of their interesting chemical properties, which have resulted in synthetic applications.’ Organosilicon chemistry has therefore become important in the methodology of organic synthesis. Despite evident POtential applications of benzofuaed sixand seven-membered heterocycles in medicinal chemistry,* only limited results are available on the silylation of heterocyclic compounds. Of particular interest in this regard is the case of quinoline derivatives that could lead to new organosilicon synthon development. The only literature in this area concerns the silylation of quinoline itself.a4 We previously showed4 that it is possible to increase yields of silylated products and modify the course of the reaction by varying the experimental conditions. We report now results on quinaldine using two silylation reagents: Me3SiCl/Li/THF and MesSiCl/ Mg/THF. The influence of the metal upon the regioand stereochemistry of silylation is probed; the chemical behavior of the N-silylated products is investigated and interpreted by quantum mechanics calculations.