89451-47-8

Upstream product

• 18413-03-1 N-(Phenacyl)pyridinium 
• 129115-49-7 2-hydroxy-2-phenyl-3-(1-pyridino)-4-(4-bromophenyl)-5-cyano-3,4-trans-1,2,3,4-tetrahydropyridine-6-thiolate 
• 68029-54-9 (E)-3-(4-bromophenyl)-2-cyanoprop-2-enethioamide 
• 7357-70-2 Cyanothioacetamide 
• 129115-45-3 1-[(Z)-1-Benzoyl-2-(4-bromo-phenyl)-vinyl]-pyridinium; bromide 
• 68029-54-9 3-(4-bromophenyl)-2-cyanoprop-2-enethioamide 
• 14990-66-0 1-(1-phenylvinyl)piperidine 
• 1122-91-4 4-bromo-benzaldehyde 
• 326-06-7 1-Phenyl-4,4,4-trifluorobutane-1,3-dione 
• 1774-66-9 3-(4-bromophenyl)-1-phenylprop-2-en-1-one 
• 129115-49-7 C₂₃H₁₈BrN₃OS 
• 22966-09-2 (2E)-3-(4-bromophenyl)-1-phenylprop-2-en-1-one 
• 95639-02-4 3-(4-Bromo-phenyl)-2,4,4-tricyano-but-3-enethioic acid amide 
• 98-86-2 acetophenone 

Downstream Products

• 94639-84-6 3-Amino-4-(4-bromo-phenyl)-6-phenyl-thieno[2,3-b]pyridine-2-carboxylic acid 
• 1127227-32-0 ethyl 3-amino-4-(4-bromophenyl)-6-phenylthieno[2,3-b]pyridine-2-carboxylate 
• 1127227-30-8 1-[3-amino-4-(4-bromophenyl)-6-phenylthieno[2,3-b]pyridin-2-yl]ethanone 
• 1127227-33-1 [3-amino-4-(4-bromophenyl)-6-phenylthieno[2,3-b]pyridin-2-yl](4-chlorophenyl)methanone 
• 1127227-31-9 3-amino-4-(4-bromophenyl)-6-phenylthieno[2,3-b]pyridine-2-carboxamide 
• 312755-04-7 C₂₇H₁₉BrN₂O₂S 
• 313531-27-0 C₂₅H₁₇BrN₂S 
• 1384529-41-2 C₂₀H₁₂BrN₃S 
• 313531-11-2 C₂₆H₁₇Br₂N₃OS 
• 94640-08-1 [4-(4-Bromo-phenyl)-3-cyano-6-phenyl-pyridin-2-ylsulfanyl]-acetic acid 

Relevant academic research and scientific papers

Reaction of 3-Amino-4,6-diarylthieno[2,3-b]pyridine-2-carboxamides with Ninhydrin

Abstract: The reaction of N-substituted amides of 3-amino-4,6-diarylthieno[2,3-b]pyridine-2-carboxylic acids with ninhydrin in the presence of catalytic amounts of sulfuric acid gave 1′-spiro[indene-2,2′-pyrido[3′,2′:4,5]thieno[3,2-d]pyrimidine]-1,3,4′(3′

New example of acyl cleavage of benzoyl-1,1,1-trifluoroacetone in a three-component synthesis of 4-aryl-2-thioxo-6-phenyl-1,2-dihydropyridine-3- carbonitriles

A three-component condensation of aromatic aldehydes, cyanothioacetamide, and benzoyl-1,1,1-trifluoroacetone, involving the acyl cleavage of the latter, results in 4-aryl-2-thioxo-6-phenyl-1,2-dihydro-pyridine-3-carbonitriles. Their alkylation was studied.

Synthesis, characterization, and reactions of pyridine-3-carbonitrile derivatives

2-Thioxopyridine-3-carbonitrile derivatives 6a-c reacted with several halogen containing reagents 7a-d to afford the corresponding thieno[2,3-b]pyridine derivatives 9a-l, respectively. Thieno[2,3-b]pyridines 9c, g,k used for the preparation of their corresponding carbohydrazide derivatives 10a-c which in turn, used as good synthons for the synthesis of N-phenylmethylenethieno[2,3-b]pyridine-2-carbohydrazides 13a-c, pyrido[3′,2′:4,5]thieno[3,2-d]pyrimidinones 15a-c, 16a-c and 17 and 1,3,4-oxadiazole-2-thiols 20a-c and 21a-c via their reactions with benzaldehyde or benzylidenemalononitrile, triethylorthoformate and carbon disulfide followed by hydrazine hydrate respectively. Considering the data of IR, 1H NMR, mass spectra, and elemental analyses elucidated the chemical structures of the newly synthesized heterocyclic compounds. Copyright Taylor & Francis Group, LLC.

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.

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 OF NITRILES. XVII. METHODS FOR THE PRODUCTION OF 4,6-DIARYL-3-CYANO-2(1H)-PYRIDINETHIONES AND THEIR MASS-SPECTROMETRIC INVESTIGATION

The boundaries of the methods for the synthesis of 2(1H)-pyridinethiones were extended.The reactions of 3-aroyl-2-aryl- and 3-aroyl-2-aryl-1-bromo-1,1-dicyanopropanes with sodium and morpholinium hydrosulfides and thiourea and of arylidenecyanothioacetamides and 3-aryl-2,4,4-tricyano-3-butenethioamides with acetophenone, and 1-(1-piperidino)-1-phenylethylene, and also the reactions of monothiodibenzoylmethane and 1,3-diphenyl-1-(1-piperidino)-1-propene-3-one with cyanothioacetamide, leading to 4,6-diaryl-3-cyano-2(1H)-pyridinethiones, were investigated.The use of substituted cyanothioacetamides seems most promising.Mass-spectrometric investigation of the obtained thiones showed that the main direction in the dissociation of their molecular ions is the elimination of the H, HS., and CS particles with the formation of the thiazepinium and pyridinium ions and the corresponding radical-cation of pyrrole.

CYCLIZATION OF NITRILES. IX. SYNTHESES BASED ON 2-ARYL-3-AROYL-1,1-DICYANOPROPANES

2-Aryl-3-aroyl-1,1-dicyanopropanes and 2-aryl-3-aroyl-1-bromo-1,1-dicyanopropanes were synthesized from chalcones and malononitrile and were converted into 4,6-diaryl-2-bromo-3-cyanopyridines and 3-cyano-2(1H)-pyridinethiones.The 2-aryl-3-aroyl-1-bromo-1,1-dicyanopropanes proved convenient intermediates for the production of the corresponding cyclopropanes and other compounds.By their reaction with urea a new method was developed for the production of substituted 3-cyano-2(1H)-pyridinethiones.The 2-bromo-3-cyanopyridines contain a mobile bromine atom readily exchanged for the various nucleophilic residues of alcohols and amines and for iodide, and cyano and thiocyanato groups.The 3-cyano-2(1H)-pyridinethiones were used in the synthesis of 3-aminothienopyridines through the isolated 2-Z-methylthio-3-cyanopyridines.

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.