- ReBr(CO)5-catalyzed knoevenagel condensation
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The Knoevenagel condensation procedure has been efficiently promoted by using a catalytic amount of ReBr(CO)5 to afford the corresponding dehydration coupling products in high yields.
- Zuo, Wei-Xiong,Hua, Ruimao,Qiu, Xianqing
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Read Online
- Novel bis-(3-cyano-2-pyridones) derivatives: synthesis and fluorescent properties
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Abstract: Novel substituted bis-(3-cyano-2-pyridone) derivatives were prepared via a powerful method using enaminonitriles push–pull dienes as key building blocks. The synthesis was performed in three steps from easily accessible starting materials in goo
- Mehiaoui, Nawel,Kibou, Zahira,Gallavardin, Thibault,Leleu, Stéphane,Franck, Xavier,Mendes, Ricardo F.,Paz, Filipe A. Almeida,Silva, Artur M. S.,Choukchou-Braham, Noureddine
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p. 1331 - 1348
(2021/01/20)
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- Ammonium chloride: An efficient and environmentally benign catalyst for knoevenagel condensation of carbonyl and active methylene compounds
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In the present study, a rapid, simple and an efficient procedure for the Knoevenagel condensation of various carbonyl and active methylene compounds in ethanol at a moderate temperature in the presence of a catalytic amount of an efficient, environmentall
- Tasqeeruddin,Asiri, Yahya I.,Mujahid Alam
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p. 3024 - 3028
(2021/01/06)
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- Base-mediated benzannulation of α-cyanocrotonates with ynones: Facile synthesis of benzonitriles and fluorenes
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Here, we have demonstrated a strategic rapid approach for the synthesis of benzonitriles and cyanofluorenes via the [3 + 3] benzannulation of readily available alkynones and α-cyanocrotonates, a protocol par excellence for aryl nitriles. This decarboxylat
- Maddi, Sridhar Reddy,Nagireddy, Attunuri,Singam, Maneesh Kumar Reddy
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supporting information
p. 2370 - 2374
(2020/05/22)
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- "on Water" Direct Catalytic Vinylogous Aldol Reaction of Silyl Glyoxylates
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The unique reactivity of water in the direct catalytic vinylogous aldol reaction of silyl glyoxylates is reported. With the hydrogen-bonding networks from water, the unfavorable homogeneous reactions in organic solvents were severely suppressed, and the "
- Pan, Hong,Han, Man-Yi,Li, Pinhua,Wang, Lei
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p. 14281 - 14290
(2019/11/03)
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- Design, Synthesis, and Biological Evaluation of 6-Substituted Thieno[3,2- d]pyrimidine Analogues as Dual Epidermal Growth Factor Receptor Kinase and Microtubule Inhibitors
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The clinical evidence for the success of tyrosine kinase inhibitors in combination with microtubule-targeting agents prompted us to design and develop single agents that possess both epidermal growth factor receptor (EGFR) kinase and tubulin polymerization inhibitory properties. A series of 6-aryl/heteroaryl-4-(3′,4′,5′-trimethoxyanilino)thieno[3,2-d]pyrimidine derivatives were discovered as novel dual tubulin polymerization and EGFR kinase inhibitors. The 4-(3′,4′,5′-trimethoxyanilino)-6-(p-tolyl)thieno[3,2-d]pyrimidine derivative 6g was the most potent compound of the series as an antiproliferative agent, with half-maximal inhibitory concentration (IC50) values in the single- or double-digit nanomolar range. Compound 6g bound to tubulin in the colchicine site and inhibited tubulin assembly with an IC50 value of 0.71 μM, and 6g inhibited EGFR activity with an IC50 value of 30 nM. Our data suggested that the excellent in vitro and in vivo profile of 6g may be derived from its dual inhibition of tubulin polymerization and EGFR kinase.
- Romagnoli, Romeo,Prencipe, Filippo,Oliva, Paola,Baraldi, Stefania,Baraldi, Pier Giovanni,Schiaffino Ortega, Santiago,Chayah, Mariem,Kimatrai Salvador, Maria,Lopez-Cara, Luisa Carlota,Brancale, Andrea,Ferla, Salvatore,Hamel, Ernest,Ronca, Roberto,Bortolozzi, Roberta,Mariotto, Elena,Mattiuzzo, Elena,Viola, Giampietro
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supporting information
p. 1274 - 1290
(2019/01/30)
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- Polypharmacological profile of 1,2-dihydro-2-oxo-pyridine-3-carboxamides in the endocannabinoid system
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The endocannabinoid system (ECS) represents one of the major neuromodulatory systems involved in different physiological and pathological processes. Multi-target compounds exert their activities by acting via multiple mechanisms of action and represent a promising pharmacological modulation of the ECS. In this work we report 4-substituted and 4,5-disubstituted 1,2-dihydro-2-oxo-pyridine-3-carboxamide derivatives with a broad spectrum of affinity and functional activity towards both cannabinoid receptors and additional effects on the main components of the ECS. In particular compound B3 showed high affinity for CB1R (Ki = 23.1 nM, partial agonist) and CB2R (Ki = 6.9 nM, inverse agonist) and also significant inhibitory activity (IC50 = 70 nM) on FAAH with moderate inhibition of ABHD12 (IC50 = 2.5 μΜ). Compounds B4, B5 and B6 that act as full agonists at CB1R and as partial agonists (B5 and B6) or antagonist (B4) at CB2R, exhibited an additional multi-target property by inhibiting anandamide uptake with sub-micromolar IC50 values (0.28–0.62 μΜ). The best derivatives showed cytotoxic activity on U937 lymphoblastoid cells. Finally, molecular docking analysis carried out on the three-dimensional structures of CB1R and CB2R and of FAAH allowed to rationalize the structure-activity relationships of this series of compounds.
- Chicca, Andrea,Arena, Chiara,Bertini, Simone,Gado, Francesca,Ciaglia, Elena,Abate, Mario,Digiacomo, Maria,Lapillo, Margherita,Poli, Giulio,Bifulco, Maurizio,Macchia, Marco,Tuccinardi, Tiziano,Gertsch, Jürg,Manera, Clementina
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supporting information
p. 155 - 171
(2018/05/28)
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- Direct synthesis and application of bridged diamino-functionalized periodic mesoporous organosilicas with high nitrogen contents
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Bridged diamino-functionalized periodic mesoporous organosilicas [BD-PMO(Et), Et = ethyl] materials were synthesized directly by co-condensation of 2-bis (triethoxysilyl)ethane (BTEE) and 1,4-bis[3-(tirmethoxysilyl)-propyl]ethylenediamino (BTMSEN) under acidic conditions with pluronic triblock copolymer P123 as a template. The nitrogen content in BD-PMO(Et) could be adjusted up to 40% without disturbing the ordered mesoporous structure. These materials were proved to be effective heterogeneous catalysts for the liquid-phase reactions such as Knoevenagel and Henry condensations as well as in the intermolecular cross-double-Michael addition reaction between α-methyl-β-nitrostyrene and α, β-unsaturated ketone. They exhibited comparable catalytic activities with homogeneous catalyst piperazine and can be reused for several times without any negative environmental impact.
- Zhu, Feng-Xia,Zhao, Pu-Su,Sun, Xiao-Jun,An, Li-Tao,Deng, Yong,Wu, Jia-Min
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- Synthesis and Reactivity Profile of Ylidenemalononitrile Enamines and Their Ester Analogs Towards Electrophiles and Nucleophiles
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Herein, we describe the synthesis and reactivity of enamines derived from ylidenemalononitriles and ylidenecyanoacetates. The enamine scope was expanded by (1) increasing yields of aldehyde-derived ylidenemalononitriles, (2) incorporating silyl functional
- Longstreet, Ashley R.,Rivalti, Daniel,McQuade, D. Tyler
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p. 8583 - 8596
(2015/09/15)
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- Part 1: Synthesis and visible absorption spectra of some new monoazo dyes derived from ethyl 2-amino-4-(4′-substitutedphenyl)thiophenes
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Series of monoazo dyes from some ethyl 2-amino-4-(4′- substitutedphenyl) thiophenes were prepared and characterized. The structure of the substances was confirmed by FT-IR, 1H NMR and mass spectroscopic techniques. The relationship among the structure of the dyes, their absorption characteristics and the solvatochromic and halochromic behaviors of the dyes were investigated. Introduction of electron-accepting substituent into the diazo moiety results in large bathochromic shifts in all solvents used. The dyes exhibited positive solvatochromism and their solvatochromic properties were discussed in relation to tautomerism.
- Babür, Banu,Ertan, Nermin
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p. 319 - 328
(2014/06/09)
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- Aminated poly(vinyl chloride): An efficient green catalyst for Knoevenagel condensation reactions
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Commercially available poly(vinyl chloride) have been modified with ethylene diamine to give a highly efficient reusable organocatalyst for Knoevenagel condensation in water as well as under solvent-less conditions. The reaction proceeds with high yield a
- Rajesh Krishnan,Sree Niveditha,Sreekumar
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p. 428 - 431
(2013/05/08)
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- Polystyrene-supported pyridinium chloroaluminate ionic liquid as a new heterogeneous Lewis acid catalyst for Knoevenagel condensation
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Non-hygroscopic polystyrene-supported chloroaluminate ionic liquid was prepared from the reaction of Merrifield resin with pyridine followed by reaction with aluminium chloride. This Lewis acidic ionic liquid is an environmentally friendly heterogeneous c
- Boroujeni, Kaveh Parvanak,Jafarinasab, Mina
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experimental part
p. 429 - 431
(2012/09/22)
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- Novel basic ionic liquid based on alkylammonium as efficient catalyst for Knoevenagel reaction
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The typical Knoevenagel condensation was carried out smoothly in the presence of a basic ionic liquid of N,N,N′,N′-tetramethyl-N′- hexyl-ethylenediammonium tetrafluoroborate ([TMHEDA]BF4), and 99% of yield was obtained using ethyl cyanoacetate and benzaldehyde as substrates at 60 °C for 1 h. Four reuses of the ionic liquid without dramatic decrease in catalytic activity for Knoevenagel condensation demonstrated the good stability and operability of the ionic liquid. Moreover, the typical nucleophilic addition reactions were also accomplished by the same ionic liquid to check its feasibility. The dual function of the basic ionic liquid both as solvent and catalyst, combined with simple product separation and recycling, is expected to contribute to the development of a green and environmentally friendly strategy. Copyright Taylor & Francis Group, LLC.
- Zhou, Shuai,Liu, Lu,Wang, Bo,Ma, Mingguo,Xu, Feng,Sun, Runcang
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experimental part
p. 1384 - 1391
(2012/04/10)
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- First example of organocatalysis by polystyrene-supported PAMAM dendrimers: Highly efficient and reusable catalyst for knoevenagel condensations
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This paper describes the first use of polystyrene-supported poly(amidoamine) (PAMAM) dendrimers as heterogeneous basic organocatalysts for carbon-carbon bond formation. Polystyrene-supported PAMAM dendrimers of first, second and third generations have been used as reusable base catalysts in Knoevenagel condensations of carbonyl compounds with active methylene compounds. The reactions proceed in short periods of time and with 100% selectivity. This novel catalyst eliminates the use of aromatic and halogenated solvents, as well as complex purification processes. The catalysts can be recycled ten times. Wiley-VCH Verlag GmbH & Co. KGaA, 2008.
- Krishnan, G. Rajesh,Sreekumar, Krishnapillai
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supporting information; experimental part
p. 4763 - 4768
(2009/05/07)
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- COMPOUNDS
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The invention provides compounds of the formula: (I) wherein R1 is aryl, heteroaryl, cycloalkyl or alkyl; R2 is H, alkyl, nitro, CO2R7, CONR5R6 or halo; R3 and R4 are H, NR5R6, NC(O)R7, halo, trifluromethyl, alkyl, CONR5R6, CO2R7, ni
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Page/Page column 24
(2008/06/13)
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- SUBSTITUED 3,4-DIHYDROTHIENO [2,3-D] PYRMIDINES AS TISSUE TRANSGLUTAMINASE INHIBITORS
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The present invention provides novel compounds and methods useful for treating transglutaminase associated disorders such as celiac spru, Alzheimer's disease and Huntington's disease. Certain compounds of the invention are tissue transglutaminase inhibito
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Page/Page column 49-50
(2010/11/08)
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- SUBSTITUTED AMINOPYRIMIDINES AS NEUROKININ ANTAGONISTS
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The invention discloses tachykinin receptor antagonists. The tachykinin family of receptors comprising the neurokinins substance P (SP), neurokinin A, and neurokinin B and related neuropeptides that are widely distributed in the peripheral and central ner
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- THIENOPYRIMIDINE DERIVATIVES AS POTASSIUM CHANNEL INHIBITORS
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The present invention provides thienopyrimidine compounds which are potasium channels inhibitors. Pharmaceutical compositions comprising the compounds and their use in the treatment of arrhythmia are also provided.
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- Organic Reactions in Ionic Liquids: Knoevenagel Condensation Catalyzed by Ethylenediammonium Diacetate
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The moisture and air stable ionic liquids 1-butyl-3-methylimidazonium tetrafluoroborate [bmim]BF4 and 1-butyl-3-methylimidazonium hexafluorophosphate [bmim]PF6 were used as 'green' recycle alternatives to volatile organic solvents (VOCs) for ethylenediammonium diacetate (EDDA) catalyzed Knoevenagel condensation between aldehydes or ketones with active methylene compounds. Both aldehydes and ketones gave satisfactory results. The ionic liquids containing catalyst EDDA were recycled several times with no decrease in yields and reaction rates. In the case of 2-hydroxybenzaldehyde, the reactions led to the formation of 3-substituted coumarins under standard reaction conditions.
- Su, Ce,Chen, Zhen-Chu,Zheng, Qin-Guo
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p. 555 - 559
(2007/10/03)
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- Famoxadone: The discovery and optimisation of a new agricultural fungicide
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Famoxadone (3-anilino-5-methyl-5-(4-phenoxyphenyl)-1,3-oxazolidine-2,4-dione), is a new agricultural fungicide recently commercialized by DuPont under the trade name Famoxate. Famoxadone is a member of a new class of oxazolidinone fungicides th
- Sternberg, Jeffrey A.,Geffken, Detlef,Adams Jr., John B.,Poestages, Reiner,Sternberg, Charlene G.,Campbell, Carlton L.,Moberg, William K.
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p. 143 - 152
(2007/10/03)
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- An easy-to-use heterogeneous catalyst for the knoevenagel condensation
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Physical mixtures of alkali and earth alkali metal carbonates and commercially available zeolites were investigated as solid catalysts for the Knoevenagel condensation. Best results for the model reaction between benzaldehyde and ethyl cyanoacetate were o
- Siebenhaar,Casagrande,Studer,Blaser
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p. 566 - 569
(2007/10/03)
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- Rate enhancement of organic reactions by microwaves at atmospheric pressure
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Several different reactions have been studied to determine whether they occur more rapidly than conventionally heated reactions at atmospheric pressure. Small rate enhancements have been observed for some reactions carried out under microwave reflux in a modified domestic microwave oven. The Knoevenagel reaction of acetophenone with ethyl cyanoacetate was shown to have a rate enhancement of 2.5 times. However this reaction showed no rate increase over conventional heating, at the same temperature, in a variable-frequency microwave oven. It is therefore probable that the small rate enhancements observed in these experiments, using microwave heating, were due to hot spots or superheating of the solvent rather than to nonthermal effects.
- Gedye,Wei
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p. 525 - 532
(2007/10/03)
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- Thermal and photoinduced reduction of ethyl (Z)-α-cyano-β-bromomethylcinnamate by 1-benzyl-1,4-dihydronicotinamide
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Thermal and photoinduced reduction of ethyl (Z)-α-cyano-β-bromomethylcinnamate (1) by coenzyme NAD(P)H model 1-benzyl-1,4-dihydronicotinamide (BNAH, 2) gives ethyl (E)-1-cyano-2-phenylcyclopropane-1-carboxylate (3) in the former case, and the (E)-4 and (Z)-5 isomers of ethyl α-cyano-β-methylcinnamate with the (E)-isomer as the major product in the latter case. The results are rationalized in terms of direct hydride transfer and electron transfer-debromination-hydrogen abstraction mechanism, respectively.
- Zhu, Xiao-Qing,Liu, You-Cheng,Li, Jin,Wang, Hong-Yi
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p. 2191 - 2193
(2007/10/03)
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- Aminopropylated MCMs as base catalysts: A comparison with aminopropylated silica
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Aminopropyl-functionalised MCMs, prepared via a one-pot method, are found to be effective base catalysts for the Knoevenagel reaction, with significant improvements in terms of turnover number and solvent dependence to the ostensibly similar aminopropylsilica.
- Macquarrie, Duncan J.,Jackson, Dominic B.
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p. 1781 - 1782
(2007/10/03)
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- Amino Groups Immobilized on Silica Gel: an Efficient and Reusable Heterogeneous Catalyst for the Knoevenagel Condensation
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Silica gel functionalized with amino groups is a useful insoluble catalyst for the Khoevenagel condensation: the reaction can be carried out under continuous-flow conditions and good yields are obtained when aromatic aldehydes, cyclohexanone, and acetophenone react with ethyl acetoacetate, ethyl cyanoacetate, and malononitrile.Lower yields are obtained in the case of ethyl benzoylacetate and acetylacetone; this fact and the easy dehydration of the aldol intermediate strongly suggest the participation of the residual free silanol groups of the matrix in the catalysis mechanism.
- Angeletti, Enrico,Canepa, Carlo,Martinetti, Giovanni,Venturello, Paolo
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p. 105 - 107
(2007/10/02)
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- CINETIQUE ET MECANISME DE LA REACTION DE KNOEVENAGEL DANS LE BENZENE-2 REACTION DU MALONITRILE ET DE LA (+) METHYL-3 CYCLOHEXANONE EN PRESENCE D'UNE AMINE PRIMARIE PURE ET DE SON MELANGE AVEC L'ACIDE ACETIQUE
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The kinetics of the reaction of (+)-3-methyl cyclohexanone with malonitrile were studied in benzene at 25 deg C, in the presence of hexylamine-acetic acid mixtures.Hexylamine gives an imine with cyclohexanone in an acid-catalyzed step.This imine then reacts quickly with malononitrile.A rate law of zero order in malononitrile is observed.Separate kinetic results obtained for the formation of the imine and for the imine-malonitrile reaction support this mechanism.Without acetic acid, a complex rate law is observed; hexylamine acts mainly as a basic catalyst.Primary amine-carboxylic acid was used as a catalyst in Knoevenagel reaction, often giving an increase in yield and a diminution in the reaction time compared with the more commonly used catalysts: piperidine, β-alanine, AcOH-AcONH4.
- Guyot, J.,Kergomard, A.
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p. 1167 - 1179
(2007/10/02)
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- SYNTHESE RADICALAIRE D'ANALGESIQUES POTENTIELS: ARYL-4 PIPERIDINES SUBSTITUEES EN 2 ET BENZOMORPHANES
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The synthesis of a series of 3-aryl 5-hexenyl amines and the cyclisations of the corresponding N-chloroamines are described.When the ring closure results from the amino radical addition to the ethylenic double bond, 2-chloromethyl 4-phenyl piperidines are obtained.These compounds lead by intramolecular Friedel-Crafts reaction to varied substituted 6,7-benzomorphanes.When the phenyl ring is substituted with a methoxyl group, the cyclisation proceeds via homolytic aromatic substitution and 4-allyl tetrahydroquinolines are formed.
- Stella, L.,Raynier, B.,Surzur, J. M.
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p. 2843 - 2854
(2007/10/02)
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