SYNTHESIS AND REACTIONS OF 3-CYANO-6-METHOXYMETHYL-4-METHYL-2(1H)-PYRIDINETHIONE

Abstract

Nucleophilic substitution of the chlorine atom in 2-chloro-3-cyano-6-methoxymethyl-4-methylpyridine by mercapto group produces the corresponding 2(1H)-pyridinethione, alkylation of which by halogenated compounds in the presence of KOH proceeds regioselectively to form S-alkyl derivatives. Thorpe–Ziegler cyclization of S-alkyl derivatives, which contain an active methylene group, yields new 3-aminothieno[2,3-b]-pyridines.

Authors: E. A. Kaigorodova, L. D. Konyushkin, S. N. Mikhailichenko, V. K. Vasilin, A. V. Sazonov, and V. G. Kul'nevich.

English Translation in Chemistry of Heterocyclic Compounds, 1999, 35 (3), pp 293-296

http://link.springer.com/article/10.1007/BF02259358