19310-60-2

Usage

InChI:InChI=1/C10H7ClN2O/c11-9-3-1-7(2-4-9)5-8(6-12)10(13)14/h1-5H,(H2,13,14)

Upstream product

• 104-88-1 4-chlorobenzaldehyde 
• 109-77-3 malononitrile 
• 107-91-5 cyanoacetic acid amide 
• 1867-38-5 4-chlorobenzylidenemalonodinitrile 
• 3395-81-1 4-chlorobenzaldehyde dimethyl acetal 
• 1352994-23-0 5-amino-3-(4-chlorophenyl)-2,3-dihydroisoxazole-4-carbonitrile 

Downstream Products

• 141811-30-5 2-amino-4-(4-chlorophenyl)?5,6,7,8,9,10-hexahydrobenzocycloocta[a]1,3-dicarbonitrile 
• 77214-26-7 C₁₇H₁₂Cl₃N₂OP 
• 131387-86-5 4-(4-chlorophenyl)-2-oxo-3-(1-pyridino)-5-cyano-3,4-trans-1,2,3,4-tetrahydro-6-pyridinolate 
• 646063-47-0 1-(4-chloro-phenyl)-3-oxo-4,10-dihydro-3H-9-oxa-4-aza-phenanthrene-2-carbonitrile 
• 883199-05-1 ethyl 4-(4-chlorophenyl)-5-cyano-2-hydroxy-6-oxo-2-(trifluoromethyl)-piperidine-3-carboxylate 
• 126393-48-4 C₁₃H₁₆ClN₃S 
• 1198400-29-1 4-cyano-5-hydroxy-2-(p-chlorophenyl)-1-piperidino(thioxo)methyl-1H-pyrazole 
• 1239897-78-9 C₂₃H₂₂ClN₃O₅ 
• 1239897-82-5 C₂₂H₁₉Cl₂N₃O₅ 
• 1239897-79-0 dimethyl 6-amino-5-carbamoyl-4-(4-chlorophenyl)-1-(4-methoxyphenyl)-1,4-dihydropyridine-2,3-dicarboxylate 
• 1239897-81-4 C₂₂H₁₉Cl₂N₃O₅ 
• 1239897-80-3 C₂₃H₂₂ClN₃O₅ 

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

Montmorillonite-KSF mediated one step synthesis of pyranochromene derivatives

One-pot three-component reaction of substituted aromatic aldehydes, 2-cyanoacetamide and 4-hydroxycoumarin in the presence of Montmorillonite-KSF (MKSF) in ethanol results in the formation of pyrano[3,2-c]chromene-3-carboxylates (5a-m) has been described. The reaction was tested in different alcohols, afforded pyrano [3,2-c] chromene-3-carboxylates (5a-m) of the corresponding alcohols in good yield. The mechanism reveals that the alcohol (as solvent) plays a major role in the inter conversion of amide to the corresponding esters with Montmorillonite KSF (M-KSF) as a catalyst. Excellent yields, inexpensive and readily available substrates, environmentally benign reaction condition, shorter reaction time, and easy workup are the major advantageous features of this protocol.

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.

Tuning the Electronic Properties of 2-Cyano-3-phenylacrylamide Derivatives

We are the first to report the synthesis of a new class of 2-cyanoarylacrylamide (2-CAA) derivatives and observe that the synthesized 2-CAA shows fluorescence properties due to the formation of a dimeric interaction of hydrogen bonds between carbonyl oxygens and amide hydrogens (C=O?H-N-C=O?H-N?); i.e., dimers are linked through dimeric N-H?O hydrogen bonds. The single-crystal X-ray structure shows molecules to be hydrogen-bonded dimers, which further form a parallel stacking arrangement, mediated by significant π-π interactions. The 1H NMR and fluorescence spectral studies indicate the coexistence of amide and iminol tautomers in solution, which can be influenced by the nature of the solvent. Further, the excitation-wavelength-dependent fluorescence spectrum and the biexponential fluorescence decay profiles suggest the presence of more than one emitting species; i.e., amide and iminol tautomers coexists in solution. We have also shown that the equilibrium between the two tautomers can be tuned by the judicious choice of electron-donating or -withdrawing substituents.

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

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.

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.

Regiospecific Mno2 catalyzed hydration of phenylmethylene malononitriles to cyanophenylacrylamides by oximes

A novel and convenient method for the regiospecific hydration of phenylmethylene malononitriles to cyanoacrylamides was developed; Scope of the method and reaction conditions were optimized extensively, the method was found to be extremely successful in h