Collect. Czech. Chem. Commun. 1982, 47, 3283-3287

Preparation of 1-phenyldihydropyridines polydeuterated in their heterocyclic ring

Josef Kuthan, Jiří Krechl and Martin Bělohradský

Department of Organic Chemistry, Prague Institute of Chemical Technology, 166 28 Prague 6


The pentadeuterated quaternary salt III reacts with aniline to give the pentadeuterated pentamethine salt IV which, on action of triethylamine, gives a mixture of 1-phenylpyridinium chlorides Va-c. The chlorides Va-c are reduced with dithionite or borohydride to mixtures of 1,4- (VIIa-c) or 1,2-dihydropyridines (VIIIa-c), respectively. A procedure has been found for obtaining the 3,4,5-trideuterated or 2,3,4,5,6-pentadeuterated products.