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Mannich BasesIminesAcetalsCinchona AlkaloidsStereoisomerismKetonesAminesCatalysisMolecular StructureRecyclingIsatinPiperidonesLewis AcidsChemistry Techniques, SyntheticCyclizationArthrodermataceaeAminationBoronStyreneStyrenesBoron Compounds
AminesAldehydesNitro-Mannich reactionProline-catalyzedSynthesisAldehydeIminesCarbonylKetonesCompoundsMethylFormaldehydeCondensationCatalyticEnantioselective ReactionAmineDerivativesMulticomponentEnzymatic reactionsChemical ReactionAminoTransformationsSubstrateSolventYieldBiginelliOxidationCatalyzesAcetaldehydeOrganicCascadeBaseImineChemistryMildSuitableHighProductProcessActive
Amines8
  • Reactions between aldimines and α-methylene carbonyls are also considered Mannich reactions because these imines form between amines and aldehydes. (wikipedia.org)
  • 140 In the Mannich reaction, primary or secondary amines or ammonia react with formaldehyde to form a Schiff base. (wikipedia.org)
  • The Mannich reaction is used in many areas of organic chemistry, Examples include: alkyl amines peptides, nucleotides, antibiotics, and alkaloids (e.g. tropinone: 142 ) agrochemicals, such as plant growth regulators polymers catalysts Formaldehyde tissue crosslinking Pharmaceutical drugs (e.g. rolitetracycline (the Mannich product of tetracycline and pyrrolidine), fluoxetine (antidepressant), tramadol and tolmetin (anti-inflammatory drug). (wikipedia.org)
  • Asymmetric reactions catalyzed by amines involving enamine intermediates were developed after the discovery of the intermolecular proline-catalyzed aldol reaction in 2000. (thieme.com)
  • An efficient, metal and base-free, chemoselective reaction of boronic acids with cyanamidyl/arylcyanamidyl radicals provides primary aryl-, heteroaryl-, and alkyl amines at ambient temperature within 1 h. (organic-chemistry.org)
  • Imines and secondary amines were synthesized selectively by a Pd-catalyzed one-pot reaction of benzyl alcohols with primary amines. (organic-chemistry.org)
  • The reactions did not require any additives and were effective for a wide range of alcohols and amines. (organic-chemistry.org)
  • The crude VIg was subjected to substitution reactions with diethylamine, pyrrolidine, piperidine, morpholine and 1-methylpiperazine in benzene at 60 °C. The obtained aminocarbamates VIa-VIe were hydrolyzed with concentrated ethanolic potassium hydroxide and gave the amines VIIa-VIIe . (cas.cz)
Aldehydes3
  • A double-crossed reaction: The use of proline as an organocatalyst enables a one-pot, direct, cross-Mannich reaction to be performed between two different aldehydes and 4-methoxyaniline in a highly syn-diastereo- and enantioselective manner (see scheme). (elsevierpure.com)
  • and β-amino aldehydes by proline-catalyzed Mannich reaction. (sigmaaldrich.com)
  • The review is summarized and systematized the published data on the multicomponent reactions of ethyl trifluoroacetoacetate, carbonyl compounds (aldehydes and ketones), and nucleophilic reagents. (researchgate.net)
Nitro-Mannich reaction3
  • soap and detergents, especially with application to automotive fuel polyetheramines from substituted branched chain alkyl ethers[citation needed] α,β-unsaturated ketones by the thermal degradation of Mannich reaction products (e.g. methyl vinyl ketone from 1-diethylamino-butan-3-one) Betti reaction Kabachnik-Fields reaction Pictet-Spengler reaction Stork enamine alkylation Nitro-Mannich reaction Smith, Michael B. (wikipedia.org)
  • The structural diversity of the products, ranging from simple heterocycles or azabicycles to complex alkaloids, iminosugars, amino acids or diamino acids and phosphonates, shows the versatility of the nitro-Mannich reaction and its potential for future developments. (uitm.edu.my)
  • Synthesis of the reported structure of piperazirum using a nitro-Mannich reaction as the key stereochemical determining step by: James C. Anderson, et al. (uitm.edu.my)
Proline-catalyzed2
  • His view changed in 2006, when his group discovered that the substrate N -tert-butoxycarbonyl ( N -Boc)-imine gave very high amounts of essentially a single enantiomer in proline-catalyzed Mannich reactions. (nature.com)
  • Xiao, W.-J. The Proline-Catalyzed Mannich Reaction and the Advent of Enamine Catalysis. (mpg.de)
Synthesis8
  • Advanced Organic Chemistry: Part B: Reactions and Synthesis (5th ed. (wikipedia.org)
  • The nitro-Mannich (aza-Henry) reaction, in which a nitroalkane and an imine react to form a β-nitroamine, is a versatile tool for target-oriented synthesis. (uitm.edu.my)
  • Although the first stereoselective reaction was developed only 20 years ago, and enantioselective and diastereoselective versions for the synthesis of non-racemic compounds soon after, there are nowadays a variety of reliable methods which can be used for the synthesis of APIs and other biologically active substances. (uitm.edu.my)
  • Stereoselective, nitro-Mannich/lactamisation cascades for the direct synthesis of heavily decorated 5-nitropiperidin-2-ones and related heterocycles by: Pavol Jakubec, et al. (uitm.edu.my)
  • But simple organic molecules such as amino acids recently burst on the scene as a third class of inexpensive catalysts for reactions with enantiomer selectivity, which are required for drug synthesis. (nature.com)
  • In 2000, List used the amino acid proline to catalyse a Mannich reaction - which combines a carbonyl, an aldehyde, and an amine compound to produce β-amino carbonyl compounds, and is used widely in the synthesis of biologically active molecules, including medicinal drugs. (nature.com)
  • Other things I tried out so far were the synthesis of the 3-methyl substituted 8-bromo-4-hydroxyquinoline through the Conrad-Limpach reaction. (sciencemadness.org)
  • This is the synthesis of the 3-substituted nitrile by the Gould-Jacobs reaction from the aniline and a ethyl (ethoxymethylene)cyanoacetate (both of which are reasonably priced too! (sciencemadness.org)
Aldehyde3
  • This one-pot oxidation-cyclocondensation reaction is performed without isolation of any intermediate (aldehyde) and thus reducing time, saving energy and raw materials. (heterocycles.jp)
  • The Duff reaction was tried out, but although it did give the desired aldehyde it did so in only 15% yield. (sciencemadness.org)
  • When the reaction is in amin excess, aldehyde proton formed and its neighbor active hydogen gives reactions. (itu.edu.tr)
Imines2
  • The first time List's group tried combining acetaldehyde with N -Boc-imines in a proline-catalysed Mannich reaction they obtained only about 1% of product. (nature.com)
  • The vinylogous Mannich reaction performed with preformed imines proceeded similarly with a preferred erythro selectivity while the condensation of 3-methyl-2-trialkylsilyloxyfurans was threo selective. (heterocycles.jp)
Carbonyl3
  • In organic chemistry, the Mannich reaction is a three-component organic reaction that involves the amino alkylation of an acidic proton next to a carbonyl (C=O) functional group by formaldehyde (H−CHO) and a primary or secondary amine (−NH2) or ammonia (NH3). (wikipedia.org)
  • The final product is a β-amino-carbonyl compound also known as a Mannich base. (wikipedia.org)
  • The Mannich reaction starts with the nucleophilic addition of an amine to a carbonyl group followed by dehydration to the Schiff base. (wikipedia.org)
Ketones1
  • On methyl ketones, the enolization and the Mannich addition can occur twice, followed by an β-elimination to yield β-amino enone derivatives. (wikipedia.org)
Compounds3
  • The Bischler-Napieralski reaction of N-(5-benzyloxy-3, 4-dimethoxyphenethyl)-3-(3-ethoxycarbonyl-4-methoxyphenyl) propionamide (XX) also gave a mixture of 3, 4-dihydroisoquinolines which was derived to the 1, 2, 3, 4-tetrahydroisoquinolines and separated into 8-hydroxy (XXIV) and 6-hydroxy (XXV) compounds. (go.jp)
  • New compounds were synthesised through modifying the N-hydrogen of indophenazine moiety with different substitution and formaldehyde by Mannich reaction. (ijpsonline.com)
  • Mannich reactions of the hydrochlorides of these compounds with paraformaldehyde and propiophenone (and 4-hydroxypropiophenone, respectively) resulted in the title compounds IIIa-IIIe, IVa,b and IVd,e . (cas.cz)
Methyl2
  • Methyl 1-substituted 5-oxo-3-pyrazolin-3-yl acetates (IV) were synthesized by the reaction of methyl 3-oxoglutarate (I) with 1-substituted hydrazine (III). (go.jp)
  • In this study, the aim is having been carried out mannich reactions with using methyl cellulose, carboxy methyl methyl cellulose and methyl hydroxy propyl cellulose which occur with using different mol ratio of dimethylamine and formaldehyde in presence of various solvents and to examination of products with various spectroscopic and quantitative methods also looking for industrial aplications like metal chellating properties. (itu.edu.tr)
Formaldehyde1
  • The mechanism of the Mannich reaction starts with the formation of an iminium ion from the amine and formaldehyde. (wikipedia.org)
Condensation2
  • The Mannich reaction is a condensation reaction. (wikipedia.org)
  • The Biginelli condensation is a versatile reaction for the generation of substituted dihydropyrimidinones [6] . (inteligand.com)
Catalytic3
  • List, B. Catalytic Three-Component Ugi Reaction. (mpg.de)
  • List, B. Catalytic Asymmetric Three-Component Acyl-Strecker Reaction. (mpg.de)
  • List, B. Catalytic One-Pot, Three-Component Acyl-Strecker Reaction. (mpg.de)
Enantioselective Reaction1
  • The ( R )- and ( S )-enantiomers of 3-benzyl-4-chromanone (homoisoflavanone) were synthesized starting with the optically active 2-benzyl-1,3-propanediol monoacetates, which were obtained via the lipase-catalyzed enantioselective reaction. (heterocycles.jp)
Amine2
  • A Chan-Lam coupling reaction of benzylic and allylic boronic esters with primary and secondary anilines provides valuable alkyl amine products. (organic-chemistry.org)
  • Reactions have been carried out using dimethylamine as amine, and using water, water+dimethylformamide, water+xylene mixture as solvent. (itu.edu.tr)
Derivatives2
  • the reaction provides gramine derivatives. (wikipedia.org)
  • Metal chellating has increased with increasing of aminomethlation or Mannich capacity, thermal stability has changed in all modificated cellulose derivatives. (itu.edu.tr)
Multicomponent1
  • Multicomponent reactions (MCRs), like the Biginelli, Mannich, Passerini, and Ugi reactions, are single-pot reactions of three or more reactants which form products containing portions of all the components. (inteligand.com)
Enzymatic reactions1
  • Thrombin catalyzes enzymatic reactions that result in the formation of fibrin, the important binding part for blood clotting. (inteligand.com)
Chemical Reaction1
  • In this example, we take a recent publication on this topic and translate the chemical reaction into a protocol for ilib diverse. (inteligand.com)
Amino1
  • Compound V , obtained by a reaction of 2-chloro-4'-fluoroacetophenone with 1-(ethoxycarbonyl)piperazine, was reduced with sodium borohydride to the amino alcohol VIf . (cas.cz)
Transformations1
  • Organocatalytic reactions are highly suitable components of cascade transformations as exemplified by the seminal work of Enders [13] . (beilstein-journals.org)
Substrate2
  • This reaction offers a broad substrate scope and good functional-group tolerance. (organic-chemistry.org)
  • article mentioned alternative solvents for the C-L reaction, but at least the 2,6-di-tert-butylphenol they dubbed as "the best solvent" wasn't working for our substrate as even a 12h reflux didn't yield any precipitate after cooling down. (sciencemadness.org)
Solvent3
  • Water and water+xylene as solvent are the best choices for the high Mannich capacity. (itu.edu.tr)
  • Molecular dynamics thermodynamic integration (MDTI) method and quantum chemical calculations at the density functional theory B3LYP 6-31+(d,p) level, which included the Tomasi model of the solvent reaction field, were applied to study the tautomeric equilibrium of Mannich base in methanol solution. (cdc.gov)
  • However, the results from quantum mechanical calculations were not as good as the results of MDTI simulations owing to inappropriate treatment of intermolecular hydrogen bonds between the solute molecule and the first shell of solvent molecules in the Tomasi model of the solvent reaction field. (cdc.gov)
Yield2
  • The present approach shows the significant outcomes such as yield up to 94%, catalyst‐free reaction, easy workup procedure and shorter period of reaction time. (researchgate.net)
  • Mannich capacity and the yield are different, besides the aminomethylation, methylol derivative has occured. (itu.edu.tr)
Biginelli1
  • The recent advances in the study of the Hantzsch and Biginelli reactions involving polyfluoroalkyl-3-oxo esters are analyzed. (researchgate.net)
Oxidation1
  • In this animated activity, learners examine the terms 'half-reaction,' 'oxidizing agent,' and 'reducing agent' and follow five interactive examples to balance equations for oxidation-reduction reactions. (bio-alive.com)
Catalyzes1
Acetaldehyde5
  • Alkynylation reaction of acetaldehyde by asymmetric catalysis has been reported. (sigmaaldrich.com)
  • Organic chemists had all but given up on acetaldehyde when it came to certain types of reactions because this deceptively simple molecule has a tendency to go through many side reactions. (nature.com)
  • Because these reactions were so extremely efficient, we decided to give acetaldehyde another try," says List. (nature.com)
  • List says pharmaceutical companies have already expressed an interest in this work and a number of researchers, including himself, are trying to use acetaldehyde in other types of chemical reactions. (nature.com)
  • The biggest challenge was not really a technical or chemical one but rather having to give up the notion that it was impossible to use acetaldehyde in these types of reactions," he says. (nature.com)
Organic1
Cascade1
  • The reaction has also been applied in cascade processes. (uitm.edu.my)
Base1
  • Learners view several movie clips that demonstrate the use of an indicator to follow the neutralization reaction that occurs when an acid and a base are mixed. (bio-alive.com)
Imine1
  • I'll try out a way to make the imine similar to the Gould-Jacobs reaction (aniline and ester heater together neat or maybe with a hint if acid catalyst) and then heat it in Ph2O as at least I know it's relatively insoluble in that. (sciencemadness.org)
Chemistry1
  • Coordinadora del grup d'investigació "Biomimetic Supramolecular Chemistry and Materials", desenvolupa la seua activitat investigadora en el àmbit dels materials orgànics supramoleculars amb especial interés en els materials biomimetics i en la seua aplicació en biomedicina i en catàlisi. (uji.es)
Mild1
Suitable1
  • The strategic use of a soft Lewis basic thiophosphinoyl group for ketimines is the key to promoting the reaction, and aliphatic ketimines serve as suitable substrates with as little as 3 mol % catalyst loading. (elsevierpure.com)
High1
  • The new proline-catalysed Mannich reaction yielded high amounts of only one enantiomer. (nature.com)
Product1
  • The mixture of XI and XII was submitted to the Mannich reaction and the product was methylated with diazomethane to 1, 2, 3, 10, 11-pentamethoxyprotoberberine (XIV). (go.jp)
Process1
  • Benjamin List's group at the Max Planck Institute for Coal Research in Mülheim an der Ruhr, Germany, have managed to tame the highly reactive molecule and use it in the Mannich reaction (a process for forming carbon-carbon bonds), opening the door to a broad range of applications in drug design. (nature.com)
Active1
  • They had optimized the reaction and were able to synthesize a newly approved anti-AIDS drug and several other biologically active substances. (nature.com)