330182-01-9

Upstream product

• 128342-41-6 4-(4-methoxyphenyl)-6-(thiophen-2-yl)-2-thioxo-1,2-dihydropyridine-3-carbonitrile 
• 79-07-2 Chloroacetamide 
• 313380-19-7 (3-cyano-4-(p-methoxyphenyl)-6-(2'-thienyl)-2-pyridinylthio)acetamide 
• 39145-31-8 2-cyano-3-(4-methoxyphenyl)thioacrylamide 
• 88-15-3 2-Acetylthiophene 
• 68029-57-2 2-cyano-3-(4-methoxyphenyl)thioacrylamide 
• 326-91-0 1,1,1-trifluoro-4-(2-thienyl)butane-2,4-dione 
• 137444-51-0 (2E)-3-(4-methoxyphenyl)-1-thiophen-2-yl-prop-2-en-1-one 

Relevant academic research and scientific papers

Studies on the synthesis of some new cyanopyridine-thione and thieno[2,3-b]pyridine derivatives

The work included in this article involves the synthesis of new cyanopyridinethiones as good synthons for new thieno[2,3-b]pyridines with anticipated biological activities. Thus, the reaction of -aryl - thiocarbamoylacrylonitrile (1a-c) with (2-thenoyl)-,-trifluoroacetone led to an unexpected formation of 4-aryl-3-cyano-6-(2-thienyl)pyridine-2(1H)-thiones (4a-c). In contrast, the reaction of 1a,b with ethyl acetoacetate produced 4-aryl-3-cyano-5-ethoxycarbonyl-6-methylpyridine-2(1H)-thiones (12a,b). The reaction of compound 4a with methyl iodide gave 2-methylthio derivative 6, which upon treatment with hydrazine hydrate furnished pyrazolopyridine 7. Treatment of 4a-c with chloroacetaimde, in the presence of sodium ethoxide, led to the formation of 3-amino-4-aryl-6-(2-thienyl)thieno[2,3-b]pyridine-2-carboxamides (8a-c). The reactions of 8a with some aromatic aldehydes and/or cycloalkanones were carried out and their products were identified. Compounds 12a,b were reacted with chloro-N-arylacetamides to give ethyl 4-aryl-2-(N-aryl) carbamoylmethylthio-3-cyano-6-methylpyridine-5-carboxylates (13a-j). Upon treatment of compounds 13a-j with sodium alkoxide in alcohol, they underwent an intramolecular Thorpe-Ziegler cyclization to furnish ethyl 3-amino-4-aryl-2-(N- aryl)carbamoyl-6-methylthieno[2,3-b]pyridine-5-carboxylates (14a-j). Compounds 14a-j, in turn, were reacted with triethyl orthoformate and/or carbon disulfide to give corresponding pyridothienopyrimidinone derivatives 15a-j and 18. Pyridothienotriazinone analogs 17a-j were synthesized via diazotisation of compounds 14a-j.

Some reactions of 2-functionalized 3-amino-4-aryl-6-(2′-thienyl)-thieno[2,3-B]-pyridines: Synthesis of new pyridothienopyrimidines, pyridothienotriazines and related fused tetracyclic systems

4-Aryl-3-cyano-6-(2′-thienyl)-pyridine-2(1H)-thiones (2a-c) were prepared and reacted with chloroacetonitrile or chloroacetamide to furnish 3-amino-4-aryl-6-(2′-thienyl)-thieno[2,3-b]pyridine-2-carbonitriles (4a-c) and 2-carboxamide analogs 6a-c respectiv