Synthesis of 6-methyl-3-cyano-5-ethylpyridine-2(1H)thione and condensed heterocycles based on this compound

Abstract

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-aminopyridol[2′,3′:2,3]thieno[4,5-d]pyrimidines.

How to Cite
Rodinovskaya, L. A.; Shestopalov, A. M.; Belukhina, E. V.; Litvinov, V. P. Chem. Heterocycl. Compd. 1995, 31, 745. [Khim. Geterotsikl. Soedin. 1995, 851.]

For this article in the English edition, see DOI https://doi.org/10.1007/BF01169072