89656-44-0Relevant articles and documents
Electrophilic formamidines. Organometallic addition to 2-methoxy pyrrolidine or piperidine N-t-butyl formamidines. Formation of 2-substituted pyrrolidines and piperidines
Gottlieb,Meyers
, p. 4723 - 4726 (1990)
The title compounds were prepared by addition of Grignard reagents to methoxyformamidines 6 and 8 in ether at room temperature. Hydrolysis gives the free secondary amines, or in cases of volatile products, their thiourea derivatives.
Regioselective synthesis of azetidines or pyrrolidines by selenium-induced cyclization of secondary homoallylic amines
Franck, Xavier,Leleu, Stéphane,Outurquin, Francis
scheme or table, p. 4437 - 4440 (2010/09/20)
Azetidines or pyrrolidines can be regioselectively obtained by selenocyclization of homoallylic amines, according to the double bond substitution.
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 (2007/10/03)
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.