97006-41-2

Upstream product

• 28162-32-5 2-(2-thienyl)-1-cyanoacrylonitrile 
• 98-03-3 thiophene-2-carbaldehyde 
• 107-91-5 cyanoacetic acid amide 
• 903563-84-8 2-(hydroxy-thiophen-2-yl-methyl)-acrylonitrile 
• 1556922-47-4 C₈H₅NOS 
• 109-77-3 malononitrile 

Downstream Products

• 59851-02-4 3-cyano-6-phenyl-4-(thiophen-2'-yl)-2(1H)-pyridone 

Relevant academic research and scientific papers

Synthesis of 2-cyanoacrylamides through Pd-catalyzed monohydration of methylenemalononitriles

A straightforward and efficient method has been developed for the synthesis of 2-cyanoacrylamide from 2-methylenemalononitriles through monohydration. A series of methylenemalononitriles underwent the reaction under mild and simple reaction conditions wit

Triflic acid-catalyzed metal-free synthesis of (: E)-2-cyanoacrylamides and 3-substituted azetidine-2,4-diones

A TfOH-catalyzed highly efficient synthesis of biologically active (E)-2-cyanoacrylamides and 3-substituted azetidine-2,4-diones has been reported with 64-94% yields under metal-free conditions. The reaction proceeds through sequential Knoevenagel condens

An efficient catalyst-free one-pot synthesis of primary amides from the aldehydes of the Baylis-Hillman reaction

Herein, a facile and efficient method for the preparation of allyl amides from the aldehyde of Baylis-Hillman adducts has been developed using a hydroxylamine/methanol system under a catalyst-free condition. The effects of solvents and temperature on the reaction and substituents on the phenyl ring have been examined. This method is best demonstrated by its advantages such as operational simplicity, moderate to excellent yields, short reaction time, and simple reaction procedure. Most importantly, the reaction proceeds smoothly in the absence of a catalyst and an external oxidant.

Homogeneous and stereoselective copper(II)-catalyzed monohydration of methylenemalononitriles to 2-cyanoacrylamides

A facile and efficient route for the homogeneous and highly stereoselective monohydration of substituted methylenemalononitriles to (E)-2-cyanoacrylamides catalyzed by copper(II) acetate monohydrate in acetic acid containing 2% water is described, and a mechanism is proposed. The protocol has proved to be suitable for the monohydration of dicyanobenzenes and 2-substituted malononitriles.

Arylcyanoacrylamides as inhibitors of the Dengue and West Nile virus proteases

The 3-aryl-2-cyanoacrylamide scaffold was designed as core pharmacophore for inhibitors of the Dengue and West Nile virus serine proteases (NS2B-NS3). A total of 86 analogs was prepared to study the structure-activity relationships in detail. Thereby, it turned out that the electron density of the aryl moiety and the central double bond have a crucial influence on the activity of the compounds, whereas the influence of substituents of the amide residue is less relevant. The para-hydroxy substituted analog was found to be the most potent inhibitor in this series with a Ki-value of 35.7 μM at the Dengue and 44.6 μM at the West Nile virus protease. The aprotinin competition assay demonstrates a direct interaction of the inhibitor molecule with active centre of the Dengue virus protease. The target selectivity was studied in a counterscreen with thrombin and found to be 2.8:1 in favor of DEN protease and 2.3:1 in favor of WNV protease, respectively.

Reaction of 3-aryl-2-cyanothioacrylamides with dimethyl acetylenecarboxylate, methyl propiolate, and N-phenylmaleimide

The reaction of cyanothioacrylamides with dimethyl acetylenedicarboxylate, methyl propiolate, and N-phenylmaleimide was studied. The reaction follows a cycloaddition pathway to give thiopyrans, irrespective of the electronic or spatial effects of the substituents in the thioamide group and in position 3 of the 1-thiabuta-1,3-diene system. The reaction is regio-and stereoselective.

Synthetic approaches towards benzo[h]quinoline-3-carbonitriles

2-Alkoxybenzo[h]quinoline-3-carbonitriles 2 were readily synthesized via Dimroth rearrangement of 2-amino-4-aryl-5,6-dihydro-4H-naphtho[1,2-b]pyran-3- carbonitriles 5 induced by ethanolic and methanolic KOH. Compounds 2 were also obtained by the reaction of 2-arylmethylidene-3,4-dihydro-1(2H)- naphthalenones 1 with malononitrile or of ylidenemalononitriles 4 with 1,2,3,4-tetrahydro-1-naphthalenone in ethanolic and methanolic KOH. The molluscicidal activity of the products towards Biomphalaria alexandrina snails was screened.