89451-46-7

Upstream product

• 7357-70-2 Cyanothioacetamide 
• 129115-44-2 1-[(Z)-1-Benzoyl-2-(4-fluoro-phenyl)-vinyl]-pyridinium; bromide 
• 125240-16-6 2,6-diamino-4-(4-fluorophenyl)-4H-thiopyran-3,5-dicarbonitrile 
• 98-86-2 acetophenone 
• 1608-51-1 4-fluorochalcone 
• 109-77-3 malononitrile 
• 137502-97-7 2-[1-(4-fluorophenyl)-3-oxo-3-phenylpropyl]malononitrile 
• 16883-69-5 N-phenacylpyridinium bromide 
• 132252-86-9 (Z)-2-Cyano-3-(4-fluoro-phenyl)-thioacrylamide 
• 326-06-7 1-Phenyl-4,4,4-trifluorobutane-1,3-dione 
• 68029-40-3 (E)-2-cyano-3-(4-fluorophenyl)prop-2-enethioamide 
• 459-57-4 4-fluorobenzaldehyde 
• 18413-03-1 N-(Phenacyl)pyridinium 
• 126985-28-2 C₂₃H₁₈FN₃OS 

Downstream Products

• 94640-05-8 [3-Cyano-4-(4-fluoro-phenyl)-6-phenyl-pyridin-2-ylsulfanyl]-acetic acid 
• 94360-79-9 ethyl 3-amino-4-(4-fluorophenyl)-6-phenylthieno[2,3-b]pyridine-2-carboxylate 
• 94639-91-5 4-(4-Fluoro-phenyl)-6-phenyl-thieno[2,3-b]pyridin-3-ylamine 
• 94655-71-7 3-Amino-4-(4-fluoro-phenyl)-6-phenyl-thieno[2,3-b]pyridine-2-carboxylic acid 
• 94639-61-9 9-(4-Fluoro-phenyl)-2-methyl-7-phenyl-pyrido[3',2':4,5]thieno[3,2-d][1,3]oxazin-4-one 
• 94639-70-0 3-acetylamino-2-carboxy-6-phenyl-4-(4-fluorophenyl)thieno<2,3-b>pyridine 
• 94655-72-8 1-[4-(4-Fluoro-phenyl)-6-phenyl-thieno[2,3-b]pyridin-3-yl]-3-phenyl-urea 
• 94655-73-9 1-(3-Chloro-phenyl)-3-[4-(4-fluoro-phenyl)-6-phenyl-thieno[2,3-b]pyridin-3-yl]-urea 
• 94655-74-0 1-(4-Chloro-phenyl)-3-[4-(4-fluoro-phenyl)-6-phenyl-thieno[2,3-b]pyridin-3-yl]-urea 

Relevant academic research and scientific papers

Unexpected formation of 4-aryl-3-cyano-6-phenylpyridine-2(1H)-thiones from the reaction of arylmethylenecyanothioacetamides with benzoyl-1,1,1- trifluoroacetone

4-Aryl-3-cyano-6-phenylpyridine-2(1H)-thiones, used in the synthesis of substituted 2-alkylthiopyridines, thieno[2,3-b]pyridines, and 1,4-di(pyridin-2-ylthio)butane, have been synthesized by the condensation of arylmethylenecyanothioacetamides with benzoyl-1,1,1-trifluoroacetone. The reaction path includes the formation of the Michael adduct which undergoes loss of the acyl group. The structure of 3-cyano-2-methylthio-4-(1-naphthyl)-6- phenylpyridine has been studied by X-ray crystallography. 2005 Springer Science+Business Media, Inc.

One-pot synthesis of 4,6-diaryl-3-cyanopyridine-2(1H)-thiones and their transformation to substituted thieno[2,3-b;4,5-b]dipyridines and pyrido[3′,2′:4,5]thieno[3,2-d]pyrimidines

4,6-Diaryl-3-cyanopyridine-2(1H)-thiones were synthesized in one step by the reaction of elemental sulfur, malononitrile, and 2-aryl-1-aroylethylenes in the presence of excess triethylamine. The products were used in one-pot syntheses of substituted thien

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

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

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.

CYCLIZATION OF NITRILES. XXXIV. TRANSFORMATION OF 4-ARYL-2,6-DIAMINO-3,5-DICYANO-4H-THIOPYRANS INTO SUBSTITUTED 4-ARYL-3-CYANO-2(1H)-PYRIDINETHIONES AND 2-AMINO-4-ARYL-7,7-DIMETHYL-5-OXO-3-CYANO-5,6,7,8-TETRAHYDRO-4H-BENZOPYRANS

The reaction of 2,6-diamino-3,5-dicyano-4H-thiopyrans with monocarbonyl and acyclic 1,3-dicarbonyl compounds leads to the elimination of malononitrile and the formation of substituted 4-aryl-3-cyano-2(1H)-pyridinethiones.The reaction with 1,3-cycloalkanediones leads to the elimination of cyanothioacetamide and the formation of 2-amino-4-aryl-3-cyano-4H-benzopyrans.

SYNTHESIS OF 3-CYANO-4,6-DIARYL-3,4-DIHYDROPYRIDINE-2-THIONES

3-Cyano-4,6-diaryl-3,4-dihydropyridine-2-thiones have been synthesized for the first time by the condensation of arylideneacetophenones or 1-piperidino-1-phenyl-2-benzoylethane with cyanothioacetamide and the 1,1-dicyano-2-aryl-3-benzoylpropane with hydrogen sulfide in the presence of bases.It has been established by PMR spectroscopy that 3-cyano-3,4-dihydropyridine-2-thiones exist in solutions in the form of mixture of cis and trans isomers.