138175-50-5

Upstream product

• 14371-10-9 (E)-3-phenylpropenal 
• 107-91-5 cyanoacetic acid amide 
• 109-77-3 malononitrile 
• 1113-55-9 2-bromo-2-cyanoacetamide 
• 104-55-2 3-phenyl-propenal 
• 5439-39-4 1,1-dicyano-4-phenylbuta-1,3-diene 

Relevant academic research and scientific papers

Potassium exchanged layered zirconium phosphate as base catalyst in Knoevenagel condensation

Potassium exchanged layered zirconium phosphate catalyzed Knoevenagel condensation of aldehydes and active methylene compounds gave the corresponding E configurated olefinic derivatives in solvent free conditions.

Cascade Synthesis of 2-Cyanoacrylamides through Deacetalization and/or Knoevenagel Condensation followed by Selective Monohydration of Acetals and Aldehydes over Solid Acid Ferrites

A new protocol of cascade synthesis for biologically active 2-cyanoacrylamides (1) was developed. The reaction proceeds over a novel magnetically retrievable solid-acid composite of iron oxide, poly(vinylpyrrolidone) and phosphotungstic acid (Fe3O4/PVP–PWA) in AcOH–H2O medium under reflux conditions. This transformation is facilitated through single-site Br?nsted acid catalyzed cascade reactions involving deacetalization and/or Knoevenagel condensation followed by selective monohydration of nitriles starting from acetals (5) and aldehydes (2) with malononitrile (3). A series of aldehydes, dimethyl and diethyl acetals, along with some heterocyclic aldehydes were successfully transformed to 2-cyanoacrylamides with >95 % yields. TEM images confirmed the coating of the PVP over nanosized Fe3O4. Stereoselective monohydration of 2-benzylidenemalononitriles (4) to E isomers was demonstrated by NOESY experiments. The catalyst could be efficiently recycled seven times on employment of both acetals and aldehydes as substrates, as a result of its magnetic nature.

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

Novel soluble myeloid cell leukemia sequence 1 (Mcl-1) inhibitor (E,E)-2-(benzylaminocarbonyl)-3-styrylacrylonitrile (4g) developed using a fragment-based approach

Based on a known nanomolar Bcl-2 homology domain 3 (BH3) mimetic 3-thiomorpholin-8-oxo-8H-acenaphtho[1,2-b] pyrrole-9-carbonitrile (S1, MW: 331), we applied a fragment-based approach to obtain BH3 mimetics with improved affinity and improved solubility in a water-ethanol (9:1) cosolvent. After the deconstruction of 1 (S1), we obtained fragment cyanoacetamide (4), which was determined to be a ligand efficiency (LE) hot part. After a rational optimization through fragment evolution beginning with fragment 4, a smaller Mcl-1 inhibitor (E,E)-2-(benzylaminocarbonyl)-3-styrylacrylonitrile (4g, MW: 288) with a 6-fold increase in affinity compared to 1 was obtained, as predicted by our optimization curve and identified by Mcl-1 protein nuclear magnetic resonance (NMR).

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.

A simple, efficient and green procedure for the Knoevenagel condensation of aldehydes with N-methylpiperazine at room temperature under solvent-free conditions

Knoevenagel condensation of aromatic, aliphatic, and heteroaromatic aldehydes with active methylene compounds such as ethylcyanoacetate, malononitrile, and cyanoacetamide proceed very smoothly at room temperature by simply mixing the ingredients together under solvent-free conditions in the presence of N-methylpiperazine in excellent yields of the E-configured products. Copyright Taylor & Francis Group, LLC.

Tellurium(IV) tetrachloride catalysed facile Knoevenagel reaction

Non-enolisable aldehydes (I) and active methylene compounds (II) react in the presence of tellurium(IV) tetrachloride (catalytic) to give the corresponding α,β-unsaturated carbonyl compounds (III) in excellent yields and high purity.

Zinc chloride as a new catalyst for Knoevenagel condensation

The Knoevenagel condensation of carbonyl substrates with acidic methylene reagents proceeds smoothly in presence of zinc chloride, without the need for solvent, to produce products of good purity in high yield.

A 'Biogenetic Like' Synthesis of Perloline, 6-(3,4-dimethoxyphenyl)-5-hydroxy-5,6-dihydrobenzonaphthyridin-4(3H)-one

9H-Indenopyridine-1(2H),9-dione, prepared by a new efficient route, reacts with 3,4-dimethoxyphenyllithium to form the keto alcohol (7), which rearranges with hydrazoic acid to form 5-(3,4-dimethoxyphenyl)benznaphthyridin-4(3H)-one.The N-oxide photolyses smoothly to yield dehydroperloline as the sole product.