STEREOCHEMICAL ASPECTS OF FORMATION OF SUBSTITUTED HYDROGENATED 3-(1-PYRIDINIO)-6-PYRIDINETHIOLATES AND SYNTHESIS OF 4,6-DIARYL-3-CYANO-2(1H)-PYRIDINETHIONES ON THEIR BASIS

Article abstract of DOI:10.1007/BF00472553

Regioselective and stereoselective methods were developed for the synthesis of 2-hydroxy-2,4-diaryl-3-(1-pyridinio)-5-cyano-3,4-trans-1,2,3,4-tetrahydropyridine-6-thiolates on the basis of the reactions of cyanoacetamide with E-1-styrylpyridinium salts or aromatic aldehydes and 1-phenacylpyridinium bromide.The products exist in the half-chair conformation with the trans-diaxial arrangement of hydrogen atoms 3 and 4.The Michael adducts in the form of the anti conformers with the synclinal arrangement of the reaction centers act as intermediates.The obtained thiolateswere converted with high yields into 4,6-diaryl-3-cyano-2(1H)-pyridinethiones.