59803-32-6

Usage

InChI:InChI=1/C12H10BrNO2/c1-2-16-12(15)10(8-14)7-9-5-3-4-6-11(9)13/h3-7H,2H2,1H3/b10-7+

Upstream product

• 105-56-6 ethyl 2-cyanoacetate 
• 6630-33-7 ortho-bromobenzaldehyde 
• 64-17-5 ethanol 
• 107-91-5 cyanoacetic acid amide 

Downstream Products

• 59803-41-7 3-(2-bromo-phenyl)-2-cyano-propionic acid ethyl ester 
• 1239019-86-3 (1R,2R)-diethyl 2-(2-bromophenyl)-1-cyanocyclopent-3-ene-1,3-dicarboxylate 
• 1372800-93-5 (1S,2R,3R)-triethyl 2'-bromo-2-cyano-1,2,3,6-tetrahydro-[1,1'-biphenyl]-2,3,4-tricarboxylate 
• 1649438-43-6 triethyl 6-amino-4-(2-bromophenyl)-1-(4-bromophenyl)-1,4-dihydropyridine-2,3,5-tricarboxylate 
• 36926-83-7 ethyl 2-aminoquinoline-3-carboxylate 
• 1575816-39-5 ethyl 3-amino-1-(2-bromophenyl)-1H-benzo[f]chromene-2-carboxylate 

Relevant academic research and scientific papers

l-Lysine Functionalized Polyacrylonitrile Fiber: A Green and Efficient Catalyst for Knoevenagel Condensation in Water

Abstract: The l-lysine functionalized polyacrylonitrile fiber (PANLF) was prepared by grafting the l-lysine into a commercially available polyacrylonitrile fiber and showed highly catalytic activity for Knoevenagel condensation reaction. With low temperature (45?°C) and short reaction time (1?h), the fiber catalyst was well applicable to Knoevenagel condensation of a wide range of aldehydes and the yields could reach up to 99%. Interestingly, only in water could the reaction take place smoothly (with a yield of 88%) and a polar micro-environment promoted reaction process had been proposed to explain this phenomenon. Besides, the fiber catalyst has advantages of easy preparation, high functional degree, strong mechanical strength and thermal stability, etc. And it can be reused at least 5 times without further treatment and performed well in scaled-up experiment (amplified 50 times) and flow chemistry experiment (no loss of catalytic activity after 48?h), which indicates its potential application in industry application. Graphical Abstract: [Figure not available: see fulltext.].

Synergistic NaBH4Reduction/Cyclization of 2-Aroylcyclopropane-1-carboxylates: Synthesis of 3-Oxabicyclo[3.1.0]hexane Derivatives

An NaBH4reduction/cyclization reaction of readily available 2-aroyl-1-cyano-3-arylcyclopropane-1-carboxylate compounds was investigated. The process results in the stereoselective synthesis of 3-oxabicyclo[3.1.0]hexane derivatives in high yield

Copper-catalyzed synthesis of quinoline derivatives via tandem Knoevenagel condensation, amination and cyclization

A novel regioselective synthesis of 2-aminoquinolines and 2-arylquinoline-3-carbonitriles is described via copper-mediated tandem reaction. Formation of substituted quinolines involves Knoevenagel condensation of ortho-bromobenzaldehyde with active methylene nitriles followed by copper-catalyzed reductive amination and intramolecular cyclization.

Direct Three-Component Synthesis of α-Cyano Acrylates Involving Cascade Knoevenagel Reaction and Esterification

A direct three-component approach has been developed for the synthesis of α-cyano acrylates starting from aldehydes, alcohols and α-cyano acetamide by employing cyanuric chloride as an organocatalyst. A class of structurally diverse α-cyano acrylates have been provided with good to excellent yields via the cascade transformation of Knoevenagel condensation and amide esterification.

Applications of caged-designed proton sponges in base-catalyzed transformations Dedicated to Professor Milan Kratochvíl for his 90th birthday anniversary.

Superbasic properties of caged proton sponges (PSs) - substituted diazatetracyclo[4.4.0.13,10.15,8]dodecanes (DTDs) - were utilized in Knoevenagel and Claisen-Schmidt condensations, the Pudovik reaction, and Michael addition. This investigation covers the influence of the solvent, reaction temperature, catalyst loadings as well as the electronic properties of substituents upon the reaction. Moreover, we provided an activity comparison between our new base and a well-known and commercially available proton sponge (DMAN). The basicity (in MeCN) of our chosen DTD (pKBH+=21.7±0.1) exceeded the prototypal PS - 1,8-bis(dimethylamino)naphthalene (DMAN, pKBH+=18.6), by three orders of magnitude. We proved that DTDs are reasonably active species in monitored reactions, which is a consequence of a hydrogen bridge angle (～130°) between the two nitrogen atoms and the captured proton. We present here syntheses of aminoindolizine, substituted 4H-chromene, and flavanones, and the unexpected formation of a bis-addition product formed after Michael addition, all under mild conditions.

Towards organo-click reactions: Development of pharmaceutical ingredients by using direct organocatalytic bio-mimetic reductions

Economic and environmentally friendly bio-mimetic one-pot three and four-component Knoevenagel-hydrogenation (K-H), five-component Knoevenagel-hydrogenation-alkylation (K-H-A) and six-component Knoevenagel-hydrogenation-alkylation-Huisgen cycloaddition (K-H-A-HC) reactions of aldehydes, CH-acids, o-phenylenediamine, alkyl halides and azides using proline, proline-metal carbonate and proline-metal carbonate-Cu I-catalysis, respectively have been developed. Many of K-H and K-H-A compounds have direct application in pharmaceutical chemistry. The Royal Society of Chemistry.

Synthesis and anti-inflammatory activity of new thiazolidine-2,4-diones, 4-thioxothiazolidinones and 2-thioxoimidazolidinones

New benzylidene imidazolidine and thiazolidine derivatives were prepared by nucleophilic addition on cyanoacrylates from substituted thioxoimidazolidinones, thiazolidinediones and thioxothiazolidinones. Anti-inflammatory activity of the synthesized thiazolidines was evaluated by the carrageenin-induced paw oedema test.