Journal of Heterocyclic Chemistry p. 913 - 922 (2020)
Update date:2022-08-05
Topics:
Shestopalov, Anatoliy M.
Rodinovskaya, Lyudmila A.
Zubarev, Andrey A.
Nesterov, Vladimir N.
Ugrak, Bogdan I.
Dutova, Tatyana Ya.
A new and facile three-component method was developed for the synthesis of polymethylene-3-cyanopyridine-2(1Н)-thiones by the domino Knoevenagel → Michael → heterocyclization → dehydrogenation reaction from cycloalkanones, cyanothioacetamide, and polymethoxy-substituted benzaldehydes. The final dehydrogenation step was found to involve arylidenecyanothioacetamide. The resulting pyridinethiones and 4-chloroacetoacetic ester were introduced into the domino SN2 → Thorpe-Ziegler → Guareschi-Thorpe reaction to synthesize tetracyclic dipyridothiophenes. Starting from these compounds, 8,9-polymethylenepyranothienodipyridines were also synthesized by the domino Knoevenagel → Michael → hetero-Thorpe-Ziegler reaction. Furthermore, a method for the synthesis of thienodipyridine annulated to the steroid skeleton is proposed.
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