21739-28-6

Upstream product

• 1149-23-1 diethyl 2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate 
• 2286-29-5 ethyl 2-cyano-3-(4-methoxyphenyl)prop-2-enoate 
• 2017-87-0 ethyl (2E)-2-cyano-3-(4-methoxyphenyl)acrylate 
• 123-11-5 4-methoxy-benzaldehyde 
• 105-56-6 ethyl 2-cyanoacetate 
• 50897-91-1 ethyl 2-cyano-3-(4-methoxyphenyl)-acrylate 
• 95-54-5 1,2-diamino-benzene 
• 6674-22-2 1,8-diazabicyclo[5.4.0]undec-7-ene 
• 3001-72-7 DBN 
• 105-13-5 4-Methoxybenzyl alcohol 

Downstream Products

• 1333147-93-5 ethyl 2-(tert-butylperoxy)-2-cyano-3-(4-methoxyphenyl)propanoate 
• 2286-29-5 ethyl 2-cyano-3-(4-methoxyphenyl)prop-2-enoate 
• 1669-49-4 3-(4-methoxyphenyl)-1-phenylpropan-1-one 

Relevant academic research and scientific papers

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.

Room Temperature, Reductive Alkylation of Activated Methylene Compounds: Carbon-Carbon Bond Formation Driven by the Rhodium-Catalyzed Water-Gas Shift Reaction

The rhodium-catalyzed water-gas shift reaction has been demonstrated to drive the reductive alkylation of several classes of activated methylene compounds at room temperature. Under catalysis by rhodium trichloride (2-3 mol %), carbon monoxide (10 bar), water (2-50 equiv), and triethylamine (2.5-7 equiv), the scope has been successfully expanded to cover a wide range of alkylating agents, including aliphatic and aromatic aldehydes, as well as cyclic ketones, in moderate to high yields. This method is comparable to, and for certain aspects, surpasses the established reductive alkylation protocols.

A substituted cyano acetate preparation method (by machine translation)

The invention discloses a substituted cyano acetate preparation method, characterized in that comprises the following steps: (I) takes the aldehyde class compound, cyano acetic acid esters (II) and (III) dihydro pyridine ester, uses water as solvent, mixe

Solvent-free preparation method for substituted cyanoacetate compound

The invention discloses a solvent-free preparation method for a substituted cyanoacetate compound. The method is characterized by comprising the following steps: subjecting an aldehyde compound (I) represented by a formula shown in the description, cyanoacetate (II) represented by a formula shown in the description and a dihydropyridine ester (III) represented by a formula shown in the description to a hybrid reaction under solvent-free conditions, and carrying out separation and purification after the reaction is completed, thereby obtaining the substituted cyanoacetate (IV) represented by a formula shown in the description. According to the method, aldehydes, cyanoacetate and dihydropyridine esters serve as raw materials for the first time, and the substituted cyanoacetate can be efficiently synthesized through a one-pot method reaction without solvents and catalysts, so that the preparation method is simple, efficient and environmentally friendly.

Base-Promoted Cascade Approach for the Preparation of Reduced Knoevenagel Adducts Using Hantzsch Esters as Reducing Agent in Water

A cascade Knoevenagel condensation-reduction approach, which was carried out in water, has been reported. Using Hantzsch esters as reducing agent, under the promotion of base, a variety of reduced Knoevenagel adducts could be easily prepared by direct alkylation of malononitrile, ethyl 2-cyanoacetate, and 2-(4-nitrophenyl)acetonitrile, respectively. Meanwhile, a gram-scale synthesis of the protocol was also realized with excellent isolated yield.

Reaction of 3-arylidenepropenoic acid derivatives with triethylamine and other amines; Unexpected reductions and vinylogations

Exposure of ethyl 2-cyano-3-(2-methoxy-5-nitrophenyl)acrylate 1f to triethylamine in hot ethanol resulted in the formation of the dihydro derivative 2f and vinylogue 3f in high yields. Single crystal X-ray data are provided for 3f. Similar reactions were observed for various analogues. The reaction was studied changing aryl substituent, amines and solvents. Pyridyl, thienyl analogues were also examined. The study was extended to cyclic molecules incorporating such systems like thiazolidinedione 8, 3-cyanocoumarin 9 and 4-arylidene-isoquinoline-2,4-diones 11. The last group gave vinylogated products, 4-cinnamylidene-isoquinolinediones and 4-hydroxylated species. A few examples of arylidene derivatives from malononitrile, ethyl acetoacetate, acetyl acetone and ethyl methylsufonylacetate were investigated. Ethyl cinnamate and β-nitrostyrene were unaffected. The reaction is considered to be possibly radical mediated, since addition of free radical quencher suppressed the reaction. Contrary to the effects of thermal conditions, irradiation of 1f in ethanol at 254 and 365 nm gave complex mixtures. A few other interesting observations in this study are noted: vinylogation of 1f with acetaldehyde to 3f; formation of 3f from 1f by the treatment with triethylamine, palladium carbon and reduction of 1f to 2f by triethylammonium formate in DMF.

Novel triethylamine mediated thermal reactions of 3-aryl-2-cyanoprop-2-enoic acid derivatives - Demethylation, reduction and vinylogation

3-Aryl-2-propenoic acid derivatives undergo interesting reactions with hot triethylamine. Substrates like 6 having a methoxyl with a nitro in the ortho and cyanoacrylic derivatives in the para positions give O-demethylated products, for example, entacapone 7. On the other hand compounds like 16 having the NO2 in the para and cyanoacrylic in the ortho position undergo reduction and vinylogation. The latter phenomenon is observed in the absence of the NO2 group also.

Atom- and step-economical preparation of reduced knoevenagel adducts using CO as a deoxygenative agent

A highly efficient one-step Rh-catalyzed preparation of reduced Knoevenagel adducts of various aldehydes and ketones with active methylene compounds has been developed. The protocol does not require an external hydrogen source and employs carbon monoxide

One-pot multistep cascade reactions over multifunctional nanocomposites with pd nanoparticles supported on amine-modified mesoporous silica

Two kinds of multifunctional nanocomposites, SBA-15-NH2/Pd-p and SBA-15-NH2/Pd-f, with platelet-like and fiber-like morphologies, respectively, were fabricated by immobilizing Pd NPs onto amine-functionalized SBA-15. Some of the amino groups acted as anchoring sites for Pd NPs, whilst the remaining groups acted as Bronsted basic sites. As a result, the composites served as excellent multifunctional heterogeneous catalysts for one-pot multistep cascade reaction sequences. Moreover,when diffusion was the rate-determine step, SBA-15-NH2/Pd-p, with small mesopores, was superior to the fiber-like control sample, owing to its short diffusion length, a lower possibility of pore clogging, and better mass transportation for the reaction species during the catalysis.

3-Butyl-1-methylimidazolinium borohydride ([bmim][BH4])-a novel reducing agent for the selective reduction of carbon-carbon double bonds in activated conjugated alkenes

A novel ionic reducing reagent, 3-butyl-1-methylimidazolium borohydride ([bmim][BH4]), was synthesized and successfully used for the selective reduction of carbon-carbon double bonds in conjugated alkenes as well as the α,β-carbon-carbon double bonds in highly activated α,β,γ,δ-unsaturated alkenes. The reagent can be regenerated and reused several times without losing its activity.