132252-87-0

Upstream product

• 132252-86-9 (Z)-2-Cyano-3-(4-fluoro-phenyl)-thioacrylamide 
• 32727-94-9 1-(2-methoxy-2-oxoethyl)pyridin-1-ium bromide 
• 107268-09-7 1-(methoxycarbonylmethyl)pyridinium iodide 
• 72752-01-3 2-Amino-4-(4-fluoro-phenyl)-1,5-dithia-spiro[5.5]undec-2-ene-3-carbonitrile 
• 94639-08-4 6-Amino-4-(4-fluoro-phenyl)-2,2-dimethyl-4H-[1,3]dithiine-5-carbonitrile 
• 7357-70-2 Cyanothioacetamide 
• 459-57-4 4-fluorobenzaldehyde 
• 97579-25-4 2-cyano-3-(4-fluorophenyl)prop-2-enethioamide 

Relevant academic research and scientific papers

CYCLIZATION OF NITRILES. XLIX. DEGENERATED STEREOSELECTIVE CROSS-RECYCLIZATION OF ENAMINONITRILES OF THE 1,3-DITHIACYCLOHEXENE AND 4H-THIOPYRAN SERIES WITH PYRIDINIUM YLIDES INTO SUBSTITUTED 3-(PYRIDINIO)-5-CYANO-3,4-TRANS-1,2,3,4-TETRAHYDRO-6-PYRIDINE-THIOLATES

The reactions of enaminonitriles of 1,3-dithiacyclohexenes and 4H-thiopyrans with pyridinium ylides proceed highly regio- and stereoselectively according to the cross-recyclization mode with the formation of substituted 3-(1-pyridino)-5-cyano-3,4-trans-1,2,3,4-tetrahydro-6-pyridinethiolates.These reactions have a common intermediate, arylmethylenecyanothioacetamide, which was used in the synthesis of substituted 6-pyridinethiolates.Because of the common nature of the structure of the initial enaminonitriles of 1,3-dithiacyclohexenes and 4H-thiopyrans, the intermediate compounds and the reaction end products, the above recyclization reactions were designated as degenerated reactions.

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

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.

Stereoselective synthesis of trans-4,5-substituted 1,4,5,6-tetrahydropyridine-2-(olates)thiolates

trans-4,5-Substituted 1,4,5,6-tetrahydropyridine-2-(olates)thiolates are prepared either from pyridinium salts and cyanoacetic acid derivatives or from pyridinium salts, aromatic aldehydes and ethyl cyanoacetate or cyanoacetamide in the presence of a base