62940-90-3

Upstream product

• 94360-09-5 3-benzoyl-1-bromo-2-phenyl-1,1-dicyanopropane 
• 2700-22-3 Benzylidenemalononitrile 
• 98-86-2 acetophenone 
• 614-47-1 1,3-diphenyl-propen-3-one 
• 109-77-3 malononitrile 
• 100-52-7 benzaldehyde 
• 95-53-4 o-toluidine 
• 94-41-7 benzalacetophenone 
• 614-20-0 3-oxo-3-phenylpropionic acid 
• 124-41-4 sodium methylate 

Downstream Products

• 58327-74-5 4,6-diphenyl-2-thioxo-1,2-dihydropyridine-3-carbonitrile 
• 94360-21-1 2-Chloro-2-(3-oxo-1,3-diphenyl-propyl)-malononitrile 
• 4604-05-1 2-chloro-4,6-diphenyl-pyridine-3-carbonitrile 
• 60847-68-9 4,6-diphenyl-2-methoxypyridine-3-carbonitrile 
• 5344-60-5 methyl 4-oxo-2,4-diphenylbutanoate 
• 6268-00-4 4-oxo-2,4-diphenylbutanenitrile 
• 1208944-44-8 2-(3-nitrophenyl)-4-oxo-4-phenylbutanenitrile 
• 614-47-1 1,3-diphenyl-propen-3-one 

Relevant academic research and scientific papers

Kinetic study of Michael addition catalyzed by N-methylimidazole in ionic liquids: Residual N-methylimidazole in ionic liquids as a strong base

Michael addition of malonodinitrile to chalcone was studied in classical organic solvent as well as in some common ionic liquids (ILs). Kinetic studies proved that the reaction proceeded faster in the studied ILs than in molecular solvents. N-methylimidaz

A dynamic kinetic asymmetric transfer hydrogenation-cyclization tandem reaction: An easy access to chiral 3,4-dihydro-2: H -pyran-carbonitriles

A chiral (mesitylene)RuCl(monosulfonated diamine) catalysed dynamic kinetic resolution (DKR)-asymmetric transfer hydrogenation (ATH) process is developed for highly enantio- (up to 99% ee) and diastereo- (up to 98:2 dr) selective reduction of challenging racemic α-aryl-γ-keto malononitriles. A spontaneous cyclization reaction of the hydrogenation products delivers a cascade process for efficient synthesis of useful enantioenriched 3,4-dihydro-2H-pyran-carbonitriles.

Cu(II)-Promoted Cascade Synthesis of Fused Imidazo-Pyridine-Carbonitriles

A Cu(II)-promoted synthesis of an aza-fused N-heterocycle having a benz-imidazopyridine scaffold is developed via an addition-cyclization reaction followed by an Ullmann-type C-N coupling between o-iodoanilines and γ-ketodinitriles. This protocol features a broad substrate scope, giving products in 32-84% yields. The compounds show excellent photoluminescence properties having two absorption maxima in the region between 270-280 and 338-350 nm and emission maxima in the range of 502-533 nm. The HOMO-LUMO energy gap of 3.49-3.57 eV was determined using Gaussian 09 at the B3LYP/6-31G (d, p) basis set level. We also demonstrated a few postsynthetic modifications.

Molecular Engineering of β-Substituted Oxoporphyrinogens for Hydrogen-Bond Donor Catalysis

A new class of bifunctional hydrogen-bond donor organocatalyst using oxoporphyrinogens having increased intramolecular hydrogen-bond donor distances is reported. Oxoporphyrinogens are highly non-planar rigid macrocycles containing a multiple hydrogen bond-forming binding site. In this work, we describe the first example of non-planar OxPs as hydrogen-bond donor catalysts prepared using a molecular engineering approach of the binding site for dual activation of substrates. The introduction of β-substituents is key to the catalytic activity and the catalysts are able to catalyze 1,4-conjugate additions and sulfa-Michael additions, as well as, Henry and aza-Henry reactions at low catalyst loadings (≤ 1 mol-%) under mild conditions. Preliminary mechanistic studies have been carried out and a possible reaction mechanism has been proposed based on the bi-functional activation of both substrates through hydrogen-bonding interactions.

Visible-light-accelerated pd-catalyzed cascade addition/ cyclization of arylboronic acids to γ- And β-ketodinitriles for the construction of 3-cyanopyridines and 3-cyanopyrrole analogues

The one-pot synthetic strategies for 2,4,6-triarylnicotinonitriles and 2,5-diaryl-1H-pyrrole-3-carbonitriles have been accomplished via a Pd-catalyzed coupling of arylboronic acid with 2-(3-oxo-1,3-diarylpropyl)malononitrile and 2-(2-oxo-2- arylethyl)malo

One-Pot Sequential Synthesis of Fused Isoquinolines via Intramolecular Cyclization/Annulation and their Photophysical Investigation

One of the cyano group of γ-keto malononitrile gets hydrolyzed selectively to an amide in the presence of copper(II) acetate monohydrate. The in situ generated amide undergo an intramolecular dehydrative cyclization to a 1,2-dihydropyridone intermediate.

Chloramphenicol base chemistry. Part 11: chloramphenicol base-derived thiourea-catalyzed enantioselective Michael addition of malononitrile to α,β-unsaturated ketones

The first chloramphenicol base-derived thiourea-catalyzed enantioselective Michael addition of malononitrile to α,β-unsaturated ketones is reported. The Michael adducts were obtained in good to excellent yields (up to 98% yield) and enantioselectivities (up to 94% ee). This reaction has a broad substrate scope to various α,β-unsaturated ketones. With this in mind, this methodology was successfully applied to the synthesis of a chiral piperidone, an advanced building block for dihydropyridinone P2X7 receptor antagonists.

Thieme Chemistry Journals Awardees - Where Are They Now? A Stereoselective Tripeptide Catalyst for Conjugate Addition Reactions of Acetophenones to Dicyanoolefins

Peptides of the type H-Pro-Pro-Xaa-NH 2 were evaluated as catalysts for conjugate addition reactions of acetophenones to cyanoolefins. Tripeptide H- d -Pro-Pro-Glu-NH 2 with a carboxylic acid moiety in the side chain of Xaa was ident

On-water magnetic NiFe2O4 nanoparticle-catalyzed Michael additions of active methylene compounds, aromatic/aliphatic amines, alcohols and thiols to conjugated alkenes

Here, we have demonstrated the Michael addition of active methylene compounds, aromatic/aliphatic amines, thiols and alcohols to conjugated alkenes using magnetic nano-NiFe2O4 as reusable catalyst in water. Nano-NiFe2O4 efficiently catalyzed the formation of C-C and C-X (X = N, S, O etc.) bond through 1,4-addition reactions.

Functionalised diimidazolium salts: The anion effect on the catalytic ability

The catalytic ability of some functionalised diimidazolium ionic liquids was tested using the Michael addition of malononitrile to t-chalcone as probe reaction. Diimidazolium salts characterized by the presence of 1-(1-imidazolylmethyl)-3,5-di-[1-(3-octylimidazolylmethyl)]benzene cation and differing in the anion structure were used. Both mono- and dianions were employed and among these some chiral anions generally used as organocatalysts were taken into account. Data collected were analysed both as function of ionic liquids structure and basicity, evaluated using the Hammett basicity function. Although the use of chiral anions did not allow performing a stereochemical control of the reaction, data collected demonstrate the high catalytic ability of the functionalised salts. Indeed, high conversions and yields were obtained under mild conditions and in significantly shorter reaction times with respect to the ones so far reported for this reaction.