705282-43-5Relevant academic research and scientific papers
Studies toward labeling cytisine with [11C]phosgene: Rapid synthesis of a δ-lactam involving a new chemoselective lithiation-annulation method
Rouden, Jacques,Seitz, Thomas,Lemoucheux, Laurent,Lasne, Marie-Claire
, p. 3787 - 3793 (2004)
With the aim of the radiolabeling of cytisine, a potent agonist of nicotinic receptors, with [11C]-phosgene, the rapid synthesis of a lactam model of our target has been studied. The key step of the δ-lactam formation is a new chemoselective lithiation-annulation method, under high dilution, of a suitable piperidinylcarbamoyl chloride. This precursor was obtained from (2-hydroxyethyl)-piperidine in a linear synthetic sequence involving a Corey-Fuchs olefination of the corresponding aldehyde, followed by a selective reduction, using a diimide equivalent, of an iodoalkyne into a (Z)-iodopropene piperidine. This alkene served as main precursor to study the cyclization according to several procedures using phosgene as the required carbonylating reagent.
