1867-37-4

Usage

Synthesis Reference(s)

Synthetic Communications, 13, p. 1033, 1983 DOI: 10.1080/00397918308082723

InChI:InChI=1/C10H8N2/c11-7-10(8-12)6-9-4-2-1-3-5-9/h1-5,10H,6H2

Upstream product

• 7216-46-8 2-cyano-3-phenylpropanamide 
• 922-64-5 1,1-dicyanoethylene 
• 71-43-2 benzene 
• 2700-22-3 Benzylidenemalononitrile 
• 613-31-0 9,10-dihydroanthracene 
• 1450-14-2 1,1,1,2,2,2-hexamethyldisilane 
• 1846-13-5 2-(Benzyl)malonoamide 
• 100-39-0 benzyl bromide 
• 109-77-3 malononitrile 
• 41470-37-5 Dicyanomethyl-anion 
• 100-44-7 benzyl chloride 
• 10026-13-8 phosphorus pentachloride 
• 1149-23-1 diethyl 2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate 
• 36937-44-7 5-benzylidene-2-morpholino-1,3-thiazol-4(5H)-one 

Downstream Products

• 24867-31-0 5-benzyl-pyrimidine-2,4,6-triamine 
• 1867-33-0 benzyl-bromo-malononitrile 
• 98993-92-1 2-benzyl-2-chloromalononitrile 
• 616-75-1 2-benzylmalonic acid 
• 645-59-0 dihydrocinnamonitrile 
• 21455-96-9 α-benzyl-α-methylmalononitrile 
• 66948-38-7 4-benzyl-1H-pyrazole 

Relevant academic research and scientific papers

Solid-Liquid Phase Transfer Catalysis I. Benzylation of Malononitrile

Benzylation of malononitrile has been carried out under solid-liquid phase-transfer catalysis conditions without solvent.The influence of different variables, such as type of base, addition of alumina, molar ratio of phase-transfer agent, temperature, tim

Copper-catalyzed enantioselective intramolecular aryl C-N coupling: Synthesis of enantioenriched 2-Oxo-1,2,3,4-tetrahydroquinoline-3-carboxamides via an asymmetric desymmetrization strategy

The differentiation of two nucleophilic amide groups in malonamides through a copper-catalyzed enantioselective intramolecular aryl C-N coupling reaction is demonstrated based on an asymmetric desymmetrization strategy. Such a method afforded enantioenriched 2-oxo-1,2,3,4-tetrahydroquinoline-3-carboxamides in high yields and moderate to good enantioselectivity.

New aspects of Knoevenagel condensation and Michael addition reactions on alkaline carbonates

The Knoevenagel condensation of malononitrile with benzaldehyde on K2CO3, Rb2CO3 and Cs2CO3 gave the condensation product benzylidenemalononitrile but the reaction proceeded to the hydrogen

Synthesis and biocatalytic ene-reduction of Knoevenagel condensation compounds by the marine-derived fungus Penicillium citrinum CBMAI 1186

The chemoselective bioreduction of α,β-unsaturated compounds is an important synthetic tool that can have applications in the synthesis of many fine chemicals and pharmaceutical molecules. The synthesis of aromatic malononitrile derivatives through Knoevenagel condensation by microwave radiation under green chemistry conditions using methanol like solvent, free base and free catalyst is here reported. In addiction the biocatalytic reduction of the C–C double bond of aromatic malononitrile derivatives by whole cells of the marine-derived fungal Penicillium citrinum CBMAI 1186 was also tested. The products catalyzed by the fungus ene-reductase were obtained in very good yields (up to >98%).

A novel bifunctional Pd-ZIF-8/rGO catalyst with spatially separated active sites for the tandem Knoevenagel condensation-reduction reaction

A novel bifunctional catalyst with spatially separated active sites was prepared by the immobilization of Pd nanoparticles (NPs) via covalent interaction and coordination of a zeolitic imidazolate framework (ZIF-8) on the surface of graphene oxide (GO), respectively, which was used as an efficient catalyst for the Knoevenagel condensation-reduction tandem reaction. The results of Fourier transform infrared spectroscopy (FT-IR), X-ray diffraction (XRD), Raman spectroscopy, UV-vis spectroscopy, X-ray photoelectron spectroscopy (XPS) and thermogravimetric analysis (TGA) demonstrated that Pd and ZIF-8 were successfully immobilized on the surface of GO, and the GO was reduced to reduced graphene oxide (rGO) using NaBH4 as the reductant in the preparation of Pd-ZIF-8/rGO. The textural properties and morphology of Pd-ZIF-8/rGO were characterized by N2 adsorption-desorption, scanning electron microscopy (SEM) and transmission electron microscopy (TEM). Pd-ZIF-8/rGO shows excellent catalytic performance in the tandem reaction with 100% benzaldehyde conversion and 98.3% selectivity to benzylmalononitrile. The excellent catalytic performance of Pd-ZIF-8/rGO in the tandem reaction is due to the high catalytic activities of spatially separated Pd NPs and ZIF-8 active sites and concentrated reactants on the surface of Pd-ZIF-8/rGO due to the π-π interaction between rGO and the reactants. The anchoring and stabilization effects of oxygenated groups of GO inhibit the aggregation and leakage of active sites, leading to good catalytic recyclability with almost unchanged catalytic activity for more than eight cycles in the tandem reaction.

Catalyst-Free [3 + 3] Annulation/Oxidation of Cyclic Amidines with Activated Olefins: When the Substrate Olefin Is Also an Oxidant

Herein we describe a catalyst-free regioselective [3 + 3] annulation/oxidation reaction of cyclic amidines such as DBU (1,8-diazabicyclo(5.4.0)undec-7-ene) and DBN (1,5-diazabicyclo(4.3.0)non-5-ene) with activated olefins, i.e., 2-arylidenemalononitriles and 2-cyano-3-aryl acrylates, to afford tricyclic 2-pyridones and pyridin-2(1H)-imines, respectively. The mechanism has been proposed based on DFT calculations. In the reaction, the cyclic amidines serve as C,N-bisnucleophiles for the cyclization, while the olefins play a dual role by acting as both reactants and oxidants.

Ionization of carbon acids in liquid ammonia

The acidities of various carbon acids in liquid ammonia (LNH3) at room temperature were determined by NMR and rates of D-exchange. There is a reasonable linear correlation of the pKas in LNH3 with those in water and DMSO of slope 0.7 and 0.8, respectively. Carbon acids with an aqueous pKa of less than 12 are fully ionized in liquid ammonia. Nucleophilic substitution of benzyl chloride by carbanions in liquid ammonia generates a Bronsted βnuc = 0.38.

Sodium borohydride as the only reagent for the efficient reductive alkylation of malononitrile with ketones and aldehydes

An efficient and convenient method for the synthesis of primary and secondary monosubstituted malononitriles has been developed. In this method, sodium borohydride in isopropanol has a catalytic effect on the initial condensation between malononitrile and

Stereoselective desymmetrizations of dinitriles to synthesize lactones

Nitriles are important organic functional groups, allowing for installation of nitrogen in organic synthesis. The Pinner reaction transforms nitriles into esters via the imidate group, but in general has previously necessitated harsh acid conditions. This

Selective Synthesis of β-Ketonitriles via Catalytic Carbopalladation of Dinitriles

A practical, convenient, and highly selective method of synthesizing β-ketonitriles from the Pd-catalyzed addition of organoboron reagents to dinitriles has been developed. This method provides excellent functional-group tolerance, a broad scope of substrates, and the convenience of using commercially available substrates. The method is expected to show further utility in future synthetic procedures.