REGIOSELECTIVE DEUTERIUM LABELING OF 1,4-DISUBSTITUTED-1,2,3,6-TETRAHYDROPYRIDINES

Reactions leading to the regioselective deuterium labeling of the 1,4- disubstituted-1,2,3,6-tetrahydropyridine system are presented. Three s ynthetic approaches were explored: Base catalyzed proton-deuteron exch ange, reductive deuteration, and ring synthesis using deuterated agent s. The methods were applied to various pyridinium salts, pyridones, an d piperidones. The syntheses of several new labeled compounds are desc ribed and a brief review of the relevant literature is included.