39145-34-1

Upstream product

• 98-01-1 furfural 
• 7357-70-2 Cyanothioacetamide 

Downstream Products

• 83989-90-6 4-(furan-2-yl)-2-sulfanylidene-1,2,5,6,7,8-hexahydroquinoline-3-carbonitrile 
• 3237-22-7 2-cyano-3-(2-furanyl)acrylonitrile 
• 889827-06-9 C₃₀H₂₈N₄O₅S 

Relevant academic research and scientific papers

Multicomponent synthesis of 2-(alkylsulfanyl)-4-[furan-2-yl-(or thiophen-2-yl)]-5,6,7,8-tetrahydroquinoline-3-carbonitriles

Abstract Substituted 2-(alkylsulfanyl)-4-[furan-2-yl(or thiophen-2-yl)]-5,6,7,8-tetrahydroquinoline-3-carbonitriles were synthesized by condensation of furfural or thiophene-2-carbaldehyde with 2-cyanoethanethioamide, 1-(cyclohex-1-en-1-yl)pyrrolidine, and alkyl halides. The structure of methyl 2-{[3-cyano-4-(thiophen-2-yl)-5,6,7,8-tetrahydroquinolin-2-yl]sulfanyl}acetate was determined by X-ray analysis.

New 4-(2-Furyl)-1,4-dihydronicotinonitriles and 1,4,5,6-Tetrahydronicotinonitriles: Synthesis, Structure, and Analgesic Activity

Abstract: A series of new hybrid molecules containing 2-furyl and partially saturated pyridine fragments was obtained based on the reaction of cyanothioacetamide with furfural and 1,3-dicarbonyl compounds. The resulting compounds were tested in vivo for analgesic activity (rats) in the orofacial trigeminal pain test. Some the tested compounds showed an antinociceptive effect, superior to that of the reference drug (metamizole sodium).

Multicomponent Synthesis and Molecular and Crystal Structure of New Derivatives of Partially Hydrogenated Quinolines

Abstract: The multicomponent condensation of aromatic aldehydes, cyanothioacetamide, 1-(cyclohex-1-en-1-yl)azepine, and α-halocarbonyl compounds was studied. As a result, new derivatives of partially hydrogenated quinolines were synthesized. The molecular and crystal structures of a number of the synthesized heterocycles were studied X-ray analysis.

New Multicomponent Synthesis of Functionalized Nitriles and Esters of 6-Alkylsulfanyl-1,4-dihydronicotinic Acids

Abstract: The multicomponent condensation of malononitrile, hydrogen sulfide, aryl orhetaryl aldehydes, 1,3-dicarbonyl compounds and alkylating reagents affordedfunctionalized nitriles and esters of 6-alkylsulfanyl-1,4-dihydronicotinicacids, their aromatic analogues and 1,4-dihydrothieno[2,3-b]pyridines.

Multicomponent synthesis and molecular structure of 3-amino-2-aroyl(alkoxycarbonyl, arylcarbamoyl)-4-aryl(hetaryl)-5-arylcarbamoyl-6-methylthieno[2,3-b]pyridines

[Figure not available: see fulltext.] A new, effective method has been developed for the synthesis of functionalized thieno[2,3-b]pyridines by multicomponent condensation reactions of aromatic and heteroaromatic aldehydes, cyanothioacetamide, acetoacetanilides, and alkylating agents containing activated methylene groups. The structures of 3-amino-2-benzoyl-4-(furan-2-yl)-6-methyl-N-phenylthieno[2,3-b]pyridine-5-carboxamide, 3-amino-N2-(4-bromophenyl)-N5-(4-chlorophenyl)-6-methyl-4-(3-methylthiophen-2-yl)thieno[2,3-b]pyridine-2,5-dicarboxamide, and 3-amino- 4-(2-chlorophenyl)-N-(4-chlorophenyl)-6-methyl-2-(4-methylbenzoyl)thieno[2,3-b]pyridine-5-carboxamide were studied by X-ray structural analysis.

Design and synthesis of pyrido[2,1- b ][1,3,5]thiadiazine library via uncatalyzed mannich-type reaction

This Research Article describes the synthesis of an over 700-member library of (8R/8S)-3-R-8-aryl-6-oxo-3,4,7,8-tetrahydro-2H,6H-pyrido[2,1-b][1,3,5]thiadiazin-9-carbonitriles by uncatalyzed Mannich-type reaction of N-methylmorpholinium (4R/4S)-4-aryl-3-cyano-6-oxo-1,4,5,6-tetrahydropyridin-2-thiolates with a set of primary amines and excessive HCHO. The scope and limitations of the reaction were studied. Starting thiolates were obtained in yields of 53-82% by multicomponent reaction of aromatic aldehydes, cyanothioacetamide, 2,2-dimethyl-1,3-dioxane-4,6-dione (Meldrum's acid), and N-methylmorpholine, followed by heterocyclization of the resulting Michael adducts.

Inhibitors of tick-borne flavivirus reproduction from structure-based virtual screening

Flaviviruses form a large family of enveloped viruses affecting millions of people over the world. To date, no specific therapy was suggested for the infected people, making the treatment exclusively symptomatic. Several attempts were performed earlier for the design of fusion inhibitors for mosquito-borne flaviviruses, whereas for the tick-borne flaviviruses such design had not been performed. We have constructed homology models of envelope glycoproteins of tick-transmitted flaviviruses with the detergent binding pocket in the open state. Molecular docking of substituted 1,4-dihydropyridines and pyrido[2,1-b][1,3,5]thiadiazines was made against these models, and 89 hits were selected for the in vitro experimental evaluation. Seventeen compounds showed significant inhibition against tick-borne encephalitis virus, Powassan virus, or Omsk hemorrhagic fever virus in the 50% plaque reduction test in PEK cells. These compounds identified through rational design are the first ones possessing reproduction inhibition activity against tick-borne flaviviruses.

Regioselective reduction of 2-cyanoprop-2-enethioamides with sodium borohydride

Treatment of 2-cyanoprop-2-enethioamides with NaBH4 in EtOH gave C-alkylated cyanothioacetamides in 62-69% yields.

Condensation of α-cyanothioacetamide with aldehydes catalyzed by Envirocat EPZG

Condensation of α-cyanothioacetamide with aldehydes has been carried out in excellent yield under mild conditions by using Envirocat EPZG as a heterogenous reusable catalyst.