A 2+3 Reductive Cyclodimerization of Quinoline by SmI2

Pyridine and its derivatives are rather difficult to reduce, and the products often undergo a very fast reoxidation to regain aromaticity. The reduction of quinoline by SmI2 results in an instantaneous [2 + 3] cyclization reaction, forming a bridged seven-membered ring within a polycyclic system.