55629-54-4

Usage

InChI:InChI=1/C10H7N3O3/c11-6-8(10(12)14)5-7-1-3-9(4-2-7)13(15)16/h1-5H,(H2,12,14)/b8-5+

Upstream product

• 61222-95-5 2-Benzoyl-3-(4-nitrophenyl)-2-propenenitrile 
• 107-91-5 cyanoacetic acid amide 
• 555-16-8 4-nitrobenzaldehdye 
• 109-77-3 malononitrile 
• 881-67-4 4-nitrobenzaldehyde dimethyl acetal 
• 2403-62-5 p-nitrobenzaldehyde diethyl acetal 
• 2700-23-4 4-Nitrobenzylidenemalononitrile 
• 7409-30-5 p-nitrobenzylamine 

Downstream Products

• 77198-62-0 2-amino-4-(4-nitro-phenyl)-5,6,7,8-tetrahydro-naphthalene-1,3-dicarbonitrile 
• 141811-32-7 2-Amino-4-(4-nitro-phenyl)-5,6,7,8,9,10-hexahydro-benzocyclooctene-1,3-dicarbonitrile 
• 141811-22-5 5-Amino-7-(4-nitro-phenyl)-indan-4,6-dicarbonitrile 
• 141811-26-9 2-Amino-4-(4-nitro-phenyl)-6,7,8,9-tetrahydro-5H-benzocycloheptene-1,3-dicarbonitrile 
• 77214-28-9 C₁₇H₁₂Cl₂N₃O₃P 
• 1138244-73-1 5-amino-3-(p-nitrophenyl)-1-(4-phenylthiazol-2-yl)-1H-pyrazole-4-carboxamide 
• 120284-61-9 3-Cyano-6-[(E)-cyanoimino]-2-(4-nitro-phenyl)-4-phenyl-piperidine-3-carboxylic acid amide 
• 94640-15-0 (4R,5S)-5-Cyano-2-methyl-4-(4-nitro-phenyl)-6-oxo-1,4,5,6-tetrahydro-pyridine-3-carboxylic acid ethyl ester 
• 94640-15-0 (4R,5R)-5-Cyano-2-methyl-4-(4-nitro-phenyl)-6-oxo-1,4,5,6-tetrahydro-pyridine-3-carboxylic acid ethyl ester 

Relevant academic research and scientific papers

Chitosan as a biodegradable heterogeneous catalyst for Knoevenagel condensation between benzaldehydes and cyanoacetamide

A natural biopolymer chitosan is being employed as heterogeneous solid base catalyst for the Knoevenagel condensation reaction between benzaldehydes and cyanoacetamide under mild reaction conditions. This reaction offers the direct synthesis of condensati

Oxidative Olefination of Benzylamine with an Active Methylene Compound Mediated by Hypervalent Iodine (III)

Hypervalent iodine-mediated oxidative olefination of amines with an active methylene compound provides a rapid gateway towards the formation of electrophilic alkenes under mild reaction conditions in good to excellent yields. This is an efficient protocol for the preparation of substituted electrophilic alkenes.

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

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.

Straightforward syntheses of nitriles, acrylates, and acrylamides in aqueous propan-1,2-diol: A catalyst free and waste free methodology

A mild, elegant, catalyst free, and waste free methodology has been developed for the clear-cut synthesis of a diverse range of nitriles, acrylates, and acrylamides in good to excellent yields using aqueous propan-1,2-diol, a green reaction medium, at ambient temperature. Operational simplicity and recyclability of the reaction medium are added advantages of the methodology.

Cascade synthesis of 2-pyridones using acrylamides and ketones

Microwave assisted non-catalytic condensation of 2-cyanoacetamide with aromatic aldehydes, and enolate mediated Michael-type addition to acrylamide followed by oxidative cyclization, produce 2-pyridones in good to excellent yield. Unsymmetrical ketones produce two regioisomeric enolates, therefore thermodynamic and kinetic products of butan-2-one and pentan-2-one have been isolated and fully characterized. This journal is

Ammonium fluoride as an inexpensive catalyst for Knoevenagel condensation in solvent-free conditions under microwave irradiation

Ammonium fluoride (NH4F) has been found to be an inexpensive catalyst for Knoevenagel condensation between aromatic aldehydes 1 and active methylene compounds 2 to afford arylidene derivatives 3 in excellent yields.

Determination of thermodynamic affinities of various polar olefins as hydride, hydrogen atom, and electron acceptors in acetonitrile

A series of 69 polar olefins with various typical structures (X) were synthesized and the thermodynamic affinities (defined in terms of the molar enthalpy changes or the standard redox potentials in this work) of the polar olefins obtaining hydride anions, hydrogen atoms, and electrons, the thermodynamic affinities of the radical anions of the polar olefins (X ?-) obtaining protons and hydrogen atoms, and the thermodynamic affinities of the hydrogen adducts of the polar olefins (XH?) obtaining electrons in acetonitrile were determined using titration calorimetry and electrochemical methods. The pure Ci - 'C π-bond heterolytic and homolytic dissociation energies of the polar olefins (X) in acetonitrile and the pure Ci - 'C π-bond homolytic dissociation energies of the radical anions of the polar olefins (X?-) in acetonitrile were estimated. The remote substituent effects on the six thermodynamic affinities of the polar olefins and their related reaction intermediates were examined using the Hammett linear free-energy relationships; the results show that the Hammett linear free-energy relationships all hold in the six chemical and electrochemical processes. The information disclosed in this work could not only supply a gap of the chemical thermodynamics of olefins as one class of very important organic unsaturated compounds but also strongly promote the fast development of the chemistry and applications of olefins.

A simple, efficient, and green protocol for Knoevenagel condensation in a cost-effective ionic liquid 2-hydroxyethlammonium formate without a catalyst

Knoevenagel condensation of aromatic aldehydes with active methylene compounds such as malononitrile, ethylcyanoacetate, and cyanoacetamide proceeded very smoothly in reusable and cheap ionic liquid 2-hydroxyethylammonium formate at room temperature in the absence of a catalyst. Compared to other reported ionic liquids, the ionic liquid 2-hydroxyethylammonium formate shows better potential in the applications on the industrial scale with its low cost and viscosity.