129115-51-1Relevant academic research and scientific papers
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
Shestopalov, A. M.,Sharanin, Yu. A.,Promonenkov, V. K.
, p. 317 - 322 (2007/10/02)
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.
CYCLIZATION REACTIONS OF NITRILES. XXXVIII. THE STEREOSELECTIVE SYNTHESIS AND TRANSFORMATIONS OF 2-HYDROXY-2,4-DIARYL-3-(1-PYRIDINO)-5-CYANO-3,4-TRANS-1,2,3,4-TETRAHYDROPYRIDINE-6-THIOLATES
Shestopalov, A. M.,Sharanin, Yu. A.,Rodinovskaya, L. A.,Litvinov, V. P.
, p. 1371 - 1375 (2007/10/02)
The reaction of arylmethylenecyanothioacetamides with N-phenacylpyridinium ylids or the three-component condensation of ylids, aromatic aldehydes, and cyanothioacetamide proceeds stereoselectively with the formation of 2-hydroxy-2,4-diaryl-3-(1-pyridino)-5-cyano-3,4-trans-1,2,3,4-tetrahydropyridine-6-thiolates, which are intermediates in the synthesis of 4,6-diaryl-3-cyanopyridine-2(1H)-thiones.The 6-thiolates obtained are found in half-chair conformation with trans-pseudoaxial arrangement of H3 and H4.
