Microwave-Assisted Iridium-Catalyzed Synthesis of Nicotine and Anabasine Derivatives

Various functionalized nicotine and anabasine analogues are synthesized via a three-step sequence that exploits a microwave-assisted iridium-catalyzed N-heterocyclization of 1,4-and 1,5-diols for the construction of the pyrrolidine and piperidine ring systems. The microwave-assisted N-heterocyclization furnishes derivatives of nicotine and anabasine in good yields (50-75%) with overall yields ranging from 30-50%.