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.Kuban State Technological University, Krasnodar 350072, Russia, and N. D. Zelinskii Institute of Organic Chemistry of the Russian Academy of Sciences, Moscow 117913; e-mail: stud@issep.rssi.ru. Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 3, pp. 337–341, March, 1999. |