SYNTHESIS OF 6-METHYL-3-CYANO-5-ETHYLPYRIDINE-2(1H)-THIONE AND CONDENSED HETEROCYCLES BASED ON THIS COMPOUND

Article abstract of DOI:10.1007/BF01169072

It has been established that the direction of formylation of methyl propyl ketone depends on the reaction conditions.By condensation of the synthesized salts of 3-hydroxymethylene-2-pentanone with cyanothioacetamide, we have synthesized 6-methyl-3-cyano-5-ethylpyridine-2(1H)-thione and 6-propyl-3-cyanopyridine-2(1H)-thione, respectively, which are alkylated regioselectively by halides ClCH2Z (Z=Alk, COOAlk, COPh, CONH2, CN) at the sulfur atom.These thiones and the derived 2-SCH2Z-3-cyanopyridines have been used in the regioselective synthesis of substituted annelated heterocycles: 3-aminothieno<2,3-b>pyridines and 4-aminopyrido<2',3':2,3>thieno<4,5-d>pyrimidines.