A reaction of methyllithium with 3 cyano 6 methylpyridine 2(1H) thione followed by alkylation of the resulting 3 acetylpyridinethione, or a direct reaction of methyllithium with 3 cyano 6 methyl 2 (methylthio)pyridine, afforded 3 acetyl 6 methyl 2 (methylthio)pyridine. The ketone obtained was examined in bromination reactions under various conditions. Bromi nation in methanol or chloroform, proceeding through the formation of sulfonium bromides, gave substituted 3 (bromoacetyl)pyridine. A reaction of 3 acetyl 6 methyl 2 (methyl thio)pyridine with N bromosuccinimide in CCl 4 afforded N (pyridinesulfenyl)succinimide. The bromo ketone was used for the synthesis of various heterocyclic compounds.Key words: 3 cyano 6 methyl 2 (methylthio)pyridine, methyllithium, 3 acetyl 6 methyl 2 (methylthio)pyridine, N (pyridinesulfenyl)succinimide, 3 bromoacetyl 6 methyl 2 (methylthio) pyridine, 4 (pyridin 3 yl)thiazole, thieno[2,3 b]pyridine, indolizine, imidazo[1,2 a]pyridine.

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Reactions of substituted 3 cyanopyridine 2(1H) thiones with methyllithium gave 3 acetylpyri dine 2(1H) thiones. The best results were achieved by adding a solid state thione to a solution of methyllithium in ether (thione : MeLi = 1 : 3). The compounds obtained and their 3 pentanoyl analogs were used to synthesize a number of fused heterocyclic systems. Key words: 3 cyanopyridine 2(1H) thiones, 3 acetylpyridine 2(1H) thiones, 3 pentanoylpyri dine 2(1H) thiones, methyllithium, thieno[2,3 b]pyridines, 3 cyanopyrido[2,3 b]thiopyrans, 4,8 dialkyl 2 cyanomethylidenepyrido[2,3 b][1,3]thiazines.

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