29197-16-8

Upstream product

• 15435-71-9 sodium acetylacetonate 
• 555-16-8 4-nitrobenzaldehdye 
• 123-54-6 acetylacetone 
• 110-89-4 piperidine 
• 56699-21-9 3-(4-nitrobenzyl)pentane-2,4-dione 
• 41002-50-0 4-acetoxy-3-penten-2-one 
• 70554-22-2 2-Benzoyloxy-penten-⁽²⁾-on-⁽⁴⁾ 
• 2929-91-1 4-nitrobenzylidene diacetate 

Downstream Products

• 116736-39-1 5-Acetyl-2-mercapto-6-methyl-4-(4-nitro-phenyl)-1,4-dihydro-pyridine-3-carbonitrile; compound with piperidine 
• 4974-45-2 cyano-acetic acid-(4-nitro-benzylidenehydrazide) 
• 127382-05-2 5-acetyl-1,2-dihydro-6-methyl-4-(4-nitrophenyl)-3H-pyrazolo<3,4-b>pyridin-3-one 
• 117490-99-0 5-Acetyl-6-methyl-2-methylsulfanyl-4-(4-nitro-phenyl)-1,4-dihydro-pyridine-3-carbonitrile 
• 117491-07-3 6-Oxy-2-methylthio-6-methyl-4-(p-nitrophenyl)-5-acetyl-3-cyano-1,4,5,6-tetrahydropyridine 
• 219553-55-6 5-acetyl-1,4-dihydro-2,6-dimethyl-4-(4-nitrophenyl)pyridine-3-carboxylic acid 
• 1049806-64-5 (2S,3S)-ethyl 4-acetyl-5-methyl-3-(4-nitrophenyl)-2,3-dihydrofuran-2-carboxylate 
• 354579-61-6 p-O₂NC₆H₄CHC(CMeNNHPh)2 
• 1350306-91-0 3-(benzylthio(4-nitrophenyl)methyl)pentane-2,4-dione 
• 1399383-42-6 ethyl 4-acetyl-1,3-dihydro-3-methyl-8-nitro-2-benzoxepine-1-carboxylate 

Relevant academic research and scientific papers

Regioselectivity-reversed asymmetric aldol reaction of 1,3-dicarbonyl compounds

Reverse regioselectivity: The first catalytic asymmetric C-1 functionalization of 1,3-dicarbonyl compounds by an aldol reaction is described, which regioselectively affords 6-hydroxyhexane-2,4-dione derivatives as the only product with high optical purity

Accelerating the optimization of enzyme-catalyzed synthesis conditionsviamachine learning and reactivity descriptors

Enzyme-catalyzed synthesis reactions are of crucial importance for a wide range of applications. An accurate and rapid selection of optimal synthesis conditions is crucial and challenging for both human knowledge and computer predictions. In this work, a

Enzyme Promiscuity as a Remedy for the Common Problems with Knoevenagel Condensation

A new protocol based on lipase-catalyzed tandem reaction toward α,β-enones/enoesters is presented. For the synthesis of the desired products the tandem process based on enzyme-catalyzed hydrolysis and Knoevenagel reaction starting from enol acetates and aldehyde is developed. The relevant impact of the reaction conditions including organic solvent, enzyme type, and temperature on the course of the reaction was revealed. It was shown that controllable release of the active methylene compound from the corresponding enol carboxylate ensured by enzymatic reaction diminishes significantly the formation of the unwanted co-products. Furthermore, this protocol was extended by including a second tandem chemoenzymatic transformation engaging various aldehyde precursors. After a careful optimization of the reaction conditions, the target products were obtained with yields up to 86 % and with excellent E/Z-selectivity.

Enantioselective Synthesis of 2,3-Dihydrofurans via Ammonium Ylides

A chiral, ammonium ylide based access to tetrasubstituted 2,3-dihydrofurans starting from readily available benzylidene dicarbonyls and bromo acetophenones has been developed. The products are obtained in moderate to good yields with excellent diasteroselectivity and good to excellent enantioselectivity (up to 99:1 e.r.). The employed chiral amine can be recovered in near quantitative yield. The transformation can be run as a three-component one-pot reaction, generating the ammonium salt and ylide in situ. The scope of this reaction includes 17 new dihydrofurans with aromatic or heteroaromatic substituents.

Antimicrobial, antioxidant and SOD activities of copper(II) complexes derived from 2-aminobenzothiazole derivatives

A series of Cu(II) complexes have been synthesized from bidentate Schiff base ligands (by condensation of Knoevenagel condensate of acetoacetanilide (obtained from substituted benzaldehydes and acetoacetanilide) and 2-aminobenzothiazole). They were charac

Knoevenagel condensation of aromatic aldehydes with active methylene compounds catalyzed by lipoprotein lipase

A screening of using different lipases to catalyze the Knoevenagel reaction was realized, and lipase lipoprotein (LPL) from Aspergillus niger showed the best catalytic performance. The reaction conditions including solvent, enzyme loading, and temperature were screened to improve the reaction efficiency. Various kinds of substrates were investigated, and almost all the target products were obtained in good to excellent yields (76-98%) with Z configuration exclusively. This procedure provides a novel, green and efficient method for the Knoevenagel condensation of aromatic aldehydes with active methylene compounds.

Enzyme catalytic promiscuity: The papain-catalyzed Knoevenagel reaction

Papain as a sustainable and inexpensive biocatalyst was used for the first time to catalyze the Knoevenagel reactions in DMSO/water. A wide range of aromatic, hetero-aromatic and α,β-unsaturated aldehydes could react with less active methylene compounds acetylacetone and ethyl acetoacetate. The products were obtained in moderate to excellent yields with Z/E selectivities of up to 100:0. This case of biocatalytic promiscuity not only widens the application of papain to new chemical transformations, but also could be developed into a potentially valuable method for organic synthesis.

A facile synthesis of trisubstituted alkenes from β-diketones and aldehydes with AlCl3 as catalyst

Preparation of trisubstituted alkenes from low-activity β-diketones and aldehydes with aluminum chloride as catalyst has been studied. The frequently used catalyst AlCl3 is used for the first time to promote this condensation. The procedure is a convenient, low toxicity, and highly efficient method for industrial synthesis of trisubstituted alkenes in high yield. Springer Science+Business Media B.V. 2011.

Efficient solvent-free knoevenagel condensation between -diketone and aldehyde catalyzed by silica sulfuric acid

Silica sulfuric acid has been utilized as an efficient heterogeneous recyclable catalyst for Knoevenagel condensation between poorly reactive β-diketones and aldehydes under solvent-free conditions. This protocol also works well with more reactive β-ketoesters. The condensation is efficient, clean, and mild. The scope and generality of the Knoevenagel condensation were investigated. The procedure led only to the Knoevenagel product, and no side product derived from a subsequent Michael βaddition of -diketone to alkene was detected at rt. Increasing temperature led to a subsequent Michael addition, and it was applied to the efficient synthesis of 9-aryl-1,8-dioxo- octahydroxanthene derivatives.

A systematic study on Knoevenagel reaction and Nazarov cyclization of less reactive carbonyl compounds using rare earth triflates and its applications

A systematic study of Knoevenagel reaction and Nazarov cyclization was made on variety of less reactive carbonyl compounds such as β-ketoesters, 1,3-diketones and cyclic active methylene compounds using Yb(OTf)3 as the catalyst. Recycling study confirms reusability of the catalyst without much loss of activity.