52906-63-5

Upstream product

• 2017-89-2 (E)-ethyl 2-cyano-3-(4-nitrophenyl)acrylate 
• 555-16-8 4-nitrobenzaldehdye 
• 105-56-6 ethyl 2-cyanoacetate 
• 2017-89-2 2-cyano-3-(4-nitrophenyl)-2-propenoic acid ethyl ester 

Downstream Products

• 2017-89-2 2-cyano-3-(4-nitrophenyl)-2-propenoic acid ethyl ester 
• 104239-16-9 2-(4-Nitro-benzyl)-acrylonitrile 

Relevant academic research and scientific papers

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.

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

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.

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.

One-pot approach for C-C bond formation through ruthenium-amido complex catalyzed tandem aldol reaction/hydrogenation

A one-pot novel and efficient approach was developed for the -alkylation of various nitriles with carbonyl compounds using ruthenium-amido complex catalyst 1. The C-C bond was formed through aldol reaction followed by hydrogenation with triethylamine-formic acid (TEAF) and 1. Moderate to high yields were obtained, and a variety of functional groups were tolerated, including nitro and chloro groups, and a furan ring. Georg Thieme Verlag Stuttgart New York.

Development of pharmaceutical drugs, drug intermediates and ingredients by using direct organo-click reactions

Here we report on our studies of the use of combinations of amino acids, amines, K2CO3 or Cs2CO3 and CuSO4/Cu for catalysing green cascade reactions. We aimed to prepare the highly reactive and substituted olefin species 7 and 8, under very mild and environmentally friendly conditions, thus giving the hydrogenated products 10 and 12 through the action of Hantzsch ester (4) by self-catalysis through decreasing the HOMO-LUMO energy gaps between olefins 7/8 and Hantzsch ester (4) through biomimetic reductions. Highly useful compounds 10 to 14 were assembled from simple substrates such as aldehydes 1, ketones 2, CH acids 3, Hantzsch ester (4) and alkyl halides 5 by diversity-oriented green synthesis involving cascade olefination/hydrogenation (O/H), olefination/hydrogenation/alkylation (O/H/A) and hydrogenation/olefination/hydrogenation (H/O/H) reaction sequences in one-pot fashion with stereospecific organo- and organo-/metal-carbonate catalysis. Highly functionalized diverse compounds such as 10 to 14 are biologically active products and have found wide applications as pharmaceutical drugs, drug intermediates and drug ingredients. For the first time in organocatalysis, we report the O/H/A/TE reaction to furnish high yields of transesterification products 11 by simply mixing the reactants under proline/K2CO3 catalysis conditions. Additionally, a novel organocatalytic H/O/H reaction sequence for the synthesis of alkyl-substituted aromatics has been developed. Furthermore, for the first time we have developed organocatalysed cascade olefination/hydrogenation/hydrolysis (O/H/H) reactions to furnish highly useful materials such as 2-oxochroman-3-carboxylic acid (14kc) and 2-amino-4H-chromene-3-carbonitrile (14kj) in good yields. Experimentally simple and environmentally friendly organocatalytic two-carbon homologation through cascade O/H/H reactions of aldehydes 1, Meldrum's acid (3c), Hantzsch ester (4) and acetic acid/triethylamine in ethanol has been demonstrated. Additionally, we have developed a green synthesis of the highly substituted 1,2,3-triazole 17 from simple substrates through a two-step combination of olefination/hydrogenation/alkylation and Huisgen cycloaddition reaction sequences under stereospecific organocopper catalysis conditions. In this paper we have found strong support for our hypothesis that, "decreasing the HOMO-LUMO energy gap between olefins 7/8 and Hantzsch ester (4) will drive the biomimetic hydrogenation reaction by self-catalysis". This self-catalysis was further confirmed with many varieties of examples. Wiley-VCH Verlag GmbH & Co. KGaA, 2008.

Monosubstituted malononitriles: Efficient one-pot reductive alkylations of malononitrile with aromatic aldehydes

A powerful new one-pot method has been developed for the reductive alkylation of malononitrile with aromatic aldehydes. This new procedure has vastly improved the yield and efficiency of the process, and increased the scope of the aromatic aldehydes. Inco

Transfer hydrogenation of activated C=C bonds catalyzed by ruthenium amido complexes: Reaction scope, limitation, and enantioselectivity

(Chemical Equation Presented) It was found that the chemoselectivity could be completely switched from C=O to C=C bonds in the transfer hydrogenation of activated α,β-unsaturated ketones catalyzed by diamine-ruthenium complex. Moreover, this addition via metal hydride had been applied to the reduction of various activated olefins. The electron-withdrawing ability of functional groups substituted on C=C bonds at the α- or β-position had strong influence on the reactivity. In addition, a wide variety of chiral diamine-Ru(II)-(arene) systems was investigated to explore the asymmetric transfer hydrogenation of prochiral α,α-dicyanoolefins. Two parameters had been systematically studied, (i) the structure of the N-sulfonylated chiral diamine ligands, in which several chiral diamines substituted on the benzene ring of DPEN were first reported, and (ii) the structure of the metal precursors, and high enantioselectivitiy (up to 89% ee) at the β-carbon was obtained.