STEREOSELECTIVE TRANSFORMATION OF 1,3-DITHIA-4-CYCLOHEXENE ENAMINONITRILES INTO SUBSTITUTED 3,4-trans-1,2,3,4-TETRAHYDROPYRIDINE-6-THIOLATES WITH PYRIDINIUM YLIDES

Article abstract of DOI:10.1007/BF00472288

4-Amino-6-aryl-2,2-dialkyl-5-cyano-1,3-dithia-4-cyclohexenes react with pyridinium ylides in thermodynamically controlled conditions with the formation of 4-aryl-2-oxo-(thioxo)-3-(1-pyridino)-5-cyano-3,4-trans-1,2,3,4-tetrahydropyridine-6-thiolates.Arylidenecyanothioacetamides act as intermediates of this recyclization, and the corresponding pyridine-6-thiolates were obtained from them by an independent method.The synthesized hydrogenated pyridine-6-thiolates are in the half-chair conformation with a trans-diaxal position of the 3-H and 4-H hydrogen atoms.