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 synthetic approaches were explored: Base catalyzed proton-deuteron exchange, reductive deuteration, and ring synthesis using deuterated agents. The methods were applied to various pyridinium salts, pyridones, and piperidones. The syntheses of several new labeled compounds are described and a brief review of the relevant literature is included. © 1997 John Wiley & Sons, Ltd.