ChemInform Abstract: Synthesis and Regioselective (3,3)Sigmatropic Rearrangement of Substituted 2‐Allylthio(seleno)‐1,4‐dihydropyridines.

Abstract

Synthesis and Regioselective (3,3)Sigmatropic Rearrangement of Substituted 2-Allylthio(seleno)-1,4-dihydropyridines. -The allylthiopyridines (III), which are prepared from the thiolates (I) , undergo sigmatropic rearrangement upon heating to produce the thiones (IV). The synthesis of the seleno analogues (VII) is achieved by condensation reaction of the keto ester (V) with the cyanoselenoacetamide (VI) followed by treatment with allyl bromide. The compounds (VI) are rearranged in refluxing benzene to give the selones (VIII). -(LITVINOV, V. P.; SHARANIN, YU. A.; GONCHARENKO, M. P.; DYACHENKO, V. D.; SHESTOPALOV, A. M.; Izv.