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Organic chemical reaction
the Knoevenagel condensation (pronounced [ˈknøːvənaːɡl̩]) reaction is a type of chemical reaction named after German chemist Emil Knoevenagel. It is
Knoevenagel_condensation
Carboxylic acid with chemical formula CH2(COOH)2
CH2(CO2H)2 + ArCHO → ArCH=CHCO2H + H2O + CO2 In this, the so-called Knoevenagel condensation, malonic acid condenses with the carbonyl group of an aldehyde
Malonic_acid
German chemist (1865–1921)
was the German chemist who established the Knoevenagel condensation reaction. The Knoevenagel condensation reaction of carbonyl compounds with active
Emil_Knoevenagel
Chemical reaction where molecules are combined and a small molecule is lost
Many variations of condensation reactions exist. Common examples include the aldol condensation and the Knoevenagel condensation, which both form water
Condensation_reaction
Type of chemical reaction
condensation: When the base is an amine and the active hydrogen compound is sufficiently activated the reaction is called a Knoevenagel condensation.
Aldol_condensation
Chemical compound
and is a variant of a Knoevenagel condensation reaction, which is one of a broader class of reactions called Henry condensations, or simply Henry reactions
Phenyl-2-nitropropene
Organic compound
ingredient in sunscreens and cosmetics. It is an ester formed by the Knoevenagel condensation of 2-ethylhexyl cyanoacetate with benzophenone. It is a viscous
Octocrylene
Class of chemical substance
functionalities. The amides are capable of base-catalyzing the Knoevenagel condensation of benzaldehyde with malononitrile. Reactions with larger nitriles
Metal–organic_framework
Chemical reaction
This condensation reaction is catalyzed by amines such as ammonia and pyridine. The first step in the ring synthesis is related to the Knoevenagel condensation
Feist–Benary_synthesis
Chemical compound
the nitrile and carbonyl, and so can be used in condensation reactions like the Knoevenagel condensation or the Michael addition. This reactivity is similar
Ethyl_cyanoacetate
Chemical reaction that removes a carboxyl group and releases carbon dioxide
important in the malonic and acetoacetic ester synthesis. The Knoevenagel condensation and they allow keto acids serve as a stabilizing protecting group
Decarboxylation
Chemical compound
sodium as base. Another way of preparing cinnamic acid is by the Knoevenagel condensation reaction. The reactants for this are benzaldehyde and malonic acid
Cinnamic_acid
Organic compounds derived from coumarin
Whereas, coumarin-pyridine hybrids have been prepared from the Knoevenagel condensation of pyridylacetontriles with substituted salicylaldehydes. Compounds
Coumarin_derivatives
Functional group of organic compounds
an aldol or Knoevenagel condensation, both in industry and in the laboratory. Some commercially significant enones produced by condensations of acetone
Α,β-Unsaturated carbonyl compound
Α,β-Unsaturated_carbonyl_compound
Chemical compound
misconception. a biodegradable de-icing agent. a catalyst in the Knoevenagel condensation and as a source of ammonia in the Borch reaction in organic synthesis
Ammonium_acetate
Heterocyclic aromatic organic compound
formaldehyde and acetaldehyde. First, acrolein is formed in a Knoevenagel condensation from the acetaldehyde and formaldehyde. The acrolein then condenses
Pyridine
Tiny device in which chemical reactions take place
operations and higher purity products. In microreactor studies a Knoevenagel condensation was performed with the channel coated with a zeolite catalyst layer
Microreactor
Method in organic chemistry
organocatalysts are based on nitrogen such as piperidine used in the Knoevenagel condensation. DMAP used in esterifications and DABCO used in the Baylis-Hillman
Organocatalysis
pyridine synthesis, Gattermann–Skita synthesis, Guareschi–Thorpe condensation, Knoevenagel–Fries modification Hantzsch–Collidin synthesis Harries ozonolysis
List_of_organic_reactions
Chemical compound
"Knoevenagel condensation of cyclic ketones with benzoylacetonitrile and N,N'-dimethylbarbituric acid. Application of sterically hindered condensation
1,3-Dimethylbarbituric_acid
Central nervous system stimulant
nitrogen-containing functional groups. In one such example, a Knoevenagel condensation of benzaldehyde with nitroethane yields phenyl-2-nitropropene.
Amphetamine
Chemical compound
heat is applied to generate Hagemann's ester. Soon after Hagemann, Emil Knoevenagel described a modified procedure to produce the same intermediate diethyl
Hagemann's_ester
Pharmaceutical compound
The 2,4-dimethoxy-5-ethoxybenzaldehyde by subjecting it to a Knoevenagel condensation with acetic acid, ammonium acetate and nitroethane, and reducing
MME_(drug)
Class of neurotransmitter modulators
acid can form a large variety of barbiturate drugs by using the Knoevenagel condensation reaction. The structure that the first benzodiazepine is based
GABAA receptor positive allosteric modulator
GABAA_receptor_positive_allosteric_modulator
Chemical irritant/tear gas
the reaction of 2-chlorobenzaldehyde and malononitrile via the Knoevenagel condensation: ClC6H4CHO + H2C(CN)2 → ClC6H4CHC(CN)2 + H2O The reaction is catalysed
CS_gas
Organic reaction
30 years after the reaction was discovered. The first step is a Knoevenagel condensation between the ketone (1) and the α-cyanoester (2) to produce the
Gewald_reaction
Reaction impacting chemical bonds
"Knoevenagel condensation of cyclic ketones with benzoylacetonitrile and N,N′-dimethylbarbituric acid. Application of sterically hindered condensation
Inverse electron-demand Diels–Alder reaction
Inverse_electron-demand_Diels–Alder_reaction
Chemical compound
reactions, Henry reactions, transesterification reactions, and Knoevenagel condensations. Deprotonation at the 7-position gives a particularly electron-rich
Triazabicyclodecene
Chemical reaction
group flanked by two carbonyls or nitriles (see for example the Knoevenagel condensation and the first steps of the malonic ester synthesis and acetoacetic
Aldol_reaction
Class of metal–organic frameworks
nanoparticles can also be used to enhance the performance in the Knoevenagel condensation reaction between benzaldehyde and malononitrile. ZIF’s have also
Zeolitic imidazolate framework
Zeolitic_imidazolate_framework
Hydrocarbon compound containing one or more C=C bonds
carbanion or its equivalent. Pre-eminent is the aldol condensation. Knoevenagel condensations are a related class of reactions that convert carbonyls into alkenes
Alkene
Chemical compound
a useful base in organic chemistry. CsF gives higher yields in Knoevenagel condensation reactions than KF or NaF. Caesium fluoride serves as a source of
Caesium_fluoride
Chemical reaction
catalyst and achieved a solvent-free room temperature reaction. The Knoevenagel–Fries modification allows for the synthesis of unsymmetrical pyridine
Hantzsch_pyridine_synthesis
IUPAC methodology for naming chemical reactions
the so-called name reactions, such as Knoevenagel condensation, Wittig reaction, Claisen–Schmidt condensation, Schotten–Baumann reaction, and Diels–Alder
IUPAC nomenclature for organic chemical transformations
IUPAC_nomenclature_for_organic_chemical_transformations
Any part of a molecule with the chemical formula –CH2–
which are often used in organic synthesis. Examples include the Knoevenagel condensation and the malonic ester synthesis. Examples of compounds that contain
Methylene_bridge
Chemical compound
(meperidine), the antagonistic effect is 1/50 of nalorphine. The Knoevenagel condensation between 3'-Methoxybutyrophenone [21550-06-1] and Ethyl cyanoacetate
Profadol
Ethyl ester of acetoacetic acid
comparable to diethyl malonate in the malonic ester synthesis or the Knoevenagel condensation. After its alkylation and saponification, thermal decarboxylation
Ethyl_acetoacetate
Chemical compound
iodide to 250 °C, to obtain 2-methylpyridine. He then performed a Knoevenagel condensation with acetaldehyde in anhydrous zinc chloride to yield 2-propenylpyridine
Coniine
Organic compound with formula CH2(CN)2
acidic, with a pKa of 11 in water. This allows it to be used in the Knoevenagel condensation, for example in the preparation of CS gas: Despite its relative
Malononitrile
achieved through borrowing hydrogen-type indirect Wittig, aldol, Knoevenagel condensations and also through various carbon nucleophiles. Related to the Guerbet
Hydrogen_auto-transfer
4-Carbon monounsaturated fatty acid
→ CH3CH=CHCO2H A number of other methods exist, including the Knoevenagel condensation of acetaldehyde with malonic acid in pyridine: The alkaline hydrolysis
Crotonic_acid
Type of chemical reaction
well as sedatives and anticonvulsants. Used in organic synthesis. Knoevenagel condensation Acetoacetic ester synthesis "Malonic Ester Synthesis". Organic
Malonic_ester_synthesis
Organic compound and isomer of vanillin
"Rapid, Efficient, and Green Synthesis of Coumarin Derivatives via Knoevenagel Condensation and Investigating Their Biological Effects". ChemistrySelect. 4
2-Hydroxy-5-methoxybenzaldehyde
2-Hydroxy-5-methoxybenzaldehyde
Chemical compound
cross-link. The formation of this bond involved an intermolecular Knoevenagel condensation followed by radical conjugate addition and nitro reduction. This
Moroidin
Class of enzymes
examples of these reactions are the (C═C) bond isomerization, Knoevenagel condensation, Morita–Baylis–Hillman reaction, and radical reactions. Biocatalysis
Ene-reductase
Nonsteroidal anti-inflammatory drug
acid to indene 6. Alternatively, this step can be performed in a Knoevenagel condensation with cyanoacetic acid, which is then further decarboxylated. The
Sulindac
Chemical compound
in only 1 step}. Knoevenagel condensation with 3-Methoxypropionitrile [110-67-8] (8) afforded [56518-39-9] (9). Finally, condensation with Guanidine [113-00-8]
Brodimoprim
Chemical compound
4-dimethoxy-5-nitrobenzaldehyde was condensed with nitromethane in a Knoevenagel reaction to give the corresponding nitrostyrene, which is reduced electrochemically
5-Nitrovanillin
acidic α-proton by pyridine (now serving a double role) akin to the Knoevenagel condensation. This intermediate displaces an acetate ligand to a diorganolead
Organolead_chemistry
Overview of and topical guide to organic chemistry
condensation Japp-Maitland condensation Knoevenagel condensation Pechmann condensation Rap-Stoermer condensation Stetter reaction Stobbe condensation
Outline_of_organic_chemistry
Chemical compound
in an acetonitrile-water solvent mixture. The first step is a Knoevenagel condensation between the barbituric acid and the aldehyde; the second step is
Indium(III)_chloride
Chemical compound
[citation needed] PPV derivatives can be also produced via the Knoevenagel condensation between a benzylic nitrile and an aromatic dialdehyde. Since this
Poly(p-phenylene_vinylene)
Chemical compound
olefin yielded 4,4-Dipropylcyclohexanone [123018-62-2] (7). The Knoevenagel condensation with ethyl 2-cyanoacetate [1187-46-8] (8) led to Cyano-(4
Atiprimod
A reaction which is closer to a true solventless reaction is a Knoevenagel condensation of ketones with (malononitrile) where a 1:1 mixture of the two
Dry_media_reaction
Group of enantiomers
Selenium-containing lumefantrine derivatives synthesised through Knoevenagel condensation (which itself is used to synthesise lumefantrine) exhibit potential
Lumefantrine
Chemical compound
Vilsmeier–Haack reaction on 2,4-dimethylpyrrole (1) gives the aldehyde (2). Knoevenagel condensation of this intermediate with oxindole (3) in the presence of base
Semaxanib
Chemical compound (C7H14O)
heptanoic acid in 95% yield. Heptanal reacts with benzaldehyde in a Knoevenagel reaction under basic catalysis with high yield and selectivity (> 90%)
Heptanal
Macrocylcic molecule
benzaldehyde bearing a meta-cyanomethyl substituent. A series of Knoevenagel condensation reactions catalyzed by various bases stitches them together to
Cyanostar
heterocyclic systems. Iminocoumarins can be formed by a variation of the Knoevenagel condensation by reaction of salicylaldehyde with substituted acetonitriles.
Iminocoumarin
Chemical compound
in the other. The substances are prepared via a Knoevenagel condensation of a thiohydantoin–phenylalanine imine with different aldehydes
Epimerox
Chemical compound
out that this compound was made by a reaction that is called a Knoevenagel condensation. (The related Perkin reaction only works with benzaldehydes and
Triphenylbromoethylene
Genus of fungi
acetyl-CoA and malonyl-CoA to produce a ketone chain that undergoes Knoevenagel aldol condensations. The second step is the formation of a fatty acid through the
Monascus
Reaction in organic chemistry
Limbach, Tetrahedron Letters 47 (2006) 3843–3847 List, B. (2010). "Emil Knoevenagel and the Roots of Aminocatalysis". Angewandte Chemie International Edition
Proline-catalyzed aldol reactions
Proline-catalyzed_aldol_reactions
symbol Elements song Elias James Corey Emerald Emil Hermann Fischer Emil Knoevenagel Emulsion Energy level Enthalpy Entropy Environmental chemistry Enzyme
Index_of_chemistry_articles
crystallographic electron microscopy Emil Knoevenagel (1865–1921) German organic chemist, known for the condensation reaction of carbonyl compounds with active
List_of_chemists
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KNOEVENAGEL CONDENSATION
KNOEVENAGEL CONDENSATION
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