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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 13, 1983 - Issue 14
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Original Articles

Effect of Metal Ions in Organic Synthesis. part XVI. Knoevenagel Condensations of Aldehydes and Tosylhydrazones with 2,4-Pentanedione by Copper (II) Chloride-Catalyzed Reaction

Orazio Attanasi Cattedra di Chimica Organica della Facoltà di Scienze, Università di Urbino, Piazza Rinascimento 6, 61029, Urbino, Italia
,
Paolino Filippone Cattedra di Chimica Organica della Facoltà di Scienze, Università di Urbino, Piazza Rinascimento 6, 61029, Urbino, Italia
&
Amedeo Mei Cattedra di Chimica Organica della Facoltà di Scienze, Università di Urbino, Piazza Rinascimento 6, 61029, Urbino, Italia
Pages 1203-1208 | Published online: 05 Dec 2006

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Sanhu Zhao, Yindi Fan, Zhijun Wang, Yongsheng Qiao & Xiaoli Jia. (2024) Knoevenagel reaction promoted by functional ionic liquids with primary and tertiary amines. Green Chemistry Letters and Reviews 17:1.
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Mortaza Mirzai & Hassan Valizadeh. (2012) Microwave-Promoted Synthesis of 3,4-Dihydropyrimidin-2(1H)-(thio)ones Using IL-ONO as Recyclable Base Catalyst Under Solvent-Free Conditions. Synthetic Communications 42:9, pages 1268-1277.
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Manoharan Karuppiah Pillai, Sooboo Singh & SreekanthB. Jonnalagadda. (2010) Solvent-Free Knoevenagel Condensation over Cobalt Hydroxyapatite. Synthetic Communications 40:24, pages 3710-3715.
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Massimo Curini, Francesco Epifano, Maria Carla Marcotullio, Ornelio Rosati & Andrè Tsadjout. (2002) POTASSIUM EXCHANGED LAYERED ZIRCONIUM PHOSPHATE AS BASE CATALYST IN KNOEVENAGEL CONDENSATION. Synthetic Communications 32:3, pages 355-362.
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Q.L. Wang, YuDao Ma & BoJun Zuo. (1997) Knoevenagel Condensation Catalyzed by USY Zeolite. Synthetic Communications 27:23, pages 4107-4110.
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Haokai Yan, Zhenhui Kou, Shengxu Li & Tao Zhang. (2023) Synthesis of sp 2 Carbon‐Conjugated Covalent Organic Framework Thin‐Films via Copper‐Surface‐Mediated Knoevenagel Polycondensation . Small 19:35.
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Nadia Aider, Baya Djebarri, Fouzia Touahra, Hatem Layeb & Djamila Halliche. (2023) Studies of the Solvent-Free Knoevenagel Condensation over Commercial NiO compared with NiO Drived from Hydrotalcites. Bulletin of Chemical Reaction Engineering & Catalysis 18:2, pages 186-199.
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Mei-Lin Tang, Jin-Feng Ning, Yu-Hui Li, Heyanhao Zhang, Mi Liu, Ye-Jun Dong & Jun Chang. (2023) Sulfoxide-mediated approach to flavones through one-pot Knoevenagel condensation/oxa-Michael addition/sulfoxide elimination process of β-(o-hydroxyaryl)-ketosulfone with arylaldehydes. Tetrahedron Letters 116, pages 154336.
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Bharat D. Dond, Rajesh P. Kale & Shivaji N. Thore. (2023) Anhydrous copper sulfate-assisted Knoevenagel condensation under neutral conditions. Chemical Papers.
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Pawan Kudale, Kanchan Gavali, Dipak Pinjari & Ganesh Chaturbhuj. (2023) A new parallel, rapid, and green Knoevenagel condensation catalyzed by in-situ generated carbonic acid (CO2 (g) in water): Application to intermediate of AMG 837. Results in Chemistry 5, pages 100833.
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Prerna Ganwir, Priyanka Bandivadekar & Ganesh Chaturbhuj. (2022) Sulfated polyborate as Bronsted acid catalyst for Knoevenagel condensation. Results in Chemistry 4, pages 100632.
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Meng-Yang Chang, Yu-Lin Tsai & Yu-Lun Chang. (2019) Gram-Scale Synthesis of 3-Sulfonyl Flavanones. The Journal of Organic Chemistry 85:2, pages 1033-1043.
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Ornelio Rosati, Daniela Lanari, Raffaella Scavo, Diana Persia, Fabio Marmottini, Morena Nocchetti, Massimo Curini & Oriana Piermatti. (2018) Zirconium potassium phosphate methyl and/or phenyl phosphonates as heterogeneous catalysts for Knoevenagel condensation under solvent free conditions. Microporous and Mesoporous Materials 268, pages 251-259.
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Fabiana Pandolfi, Marta Feroci & Isabella Chiarotto. (2018) Role of Anion and Cation in the 1‐Methyl‐3‐butyl Imidazolium Ionic Liquids BMImX: The Knoevenagel Condensation. ChemistrySelect 3:17, pages 4745-4749.
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Richard C. LarockRichard C. Larock & Gilson Zeni. 2018. Comprehensive Organic Transformations. Comprehensive Organic Transformations 1 16 .
Aziz Fihri, Christophe Len, Rajender S. Varma & Abderrahim Solhy. (2017) Hydroxyapatite: A review of syntheses, structure and applications in heterogeneous catalysis. Coordination Chemistry Reviews 347, pages 48-76.
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Deepika Choudhary, Chanchal Agrawal, Vineeta Khatri, Ranjit Thakuria & Ashok K. Basak. (2017) Transition metal and base free coupling of N-tosylhydrazones with 1,3-dicarbonyl compound. Tetrahedron Letters 58:12, pages 1132-1136.
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Andrea Nitti, Francesca Villafiorita-Monteleone, Aurora Pacini, Chiara Botta, Tersilla Virgili, Alessandra Forni, Elena Cariati, Massimo Boiocchi & Dario Pasini. (2017) Structure–activity relationship for the solid state emission of a new family of “push–pull” π-extended chromophores. Faraday Discussions 196, pages 143-161.
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Balaga Viswanadham, Jhansi Pedada, Holger B. Friedrich & Sooboo Singh. (2016) The Role of Copper Exchanged Phosphomolybdic Acid Catalyst for Knoevenagel Condensation. Catalysis Letters 146:8, pages 1470-1477.
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Balaga Viswanadham, Pedada Jhansi, Komandur V. R. Chary, Holger B. Friedrich & Sooboo Singh. (2015) Efficient Solvent Free Knoevenagel Condensation Over Vanadium Containing Heteropolyacid Catalysts. Catalysis Letters 146:2, pages 364-372.
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M. M. Mróz, S. Benedini, A. Forni, C. Botta, D. Pasini, E. Cariati & T. Virgili. (2016) Long-living optical gain induced by solvent viscosity in a push–pull molecule. Physical Chemistry Chemical Physics 18:27, pages 18289-18296.
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Sandeep Mohanty, Amrendra Kumar Roy, G. Sandeep Reddy, K.P. Vinay Kumar, B. RamaDevi, G. Bhargavi & Arun Chandra Karmakar. (2015) Knoevenagel condensation of aromatic bisulfite adducts with 2,4-thiazolidinedione in the presence of Lewis acid catalysts. Tetrahedron Letters 56:20, pages 2564-2567.
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Deepa K. Dumbre, Tibra Mozammel, PR. Selvakannan, Sharifah Bee Abdul Hamid, Vasant R. Choudhary & Suresh K. Bhargava. (2015) Thermally decomposed mesoporous Nickel Iron hydrotalcite: An active solid-base catalyst for solvent-free Knoevenagel condensation. Journal of Colloid and Interface Science 441, pages 52-58.
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L. Muralidhar & C.R. Girija. (2014) Simple and practical procedure for Knoevenagel condensation under solvent-free conditions. Journal of Saudi Chemical Society 18:5, pages 541-544.
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SURESH PATIL, SWATI D JADHAV & M B DESHMUKH. (2013) Calcined eggshell (CES): An efficient natural catalyst for Knoevenagel condensation under aqueous condition. Journal of Chemical Sciences 125:4, pages 851-857.
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Kaveh Parvanak Boroujeni & Mina Jafarinasab. (2012) Polystyrene-Supported Pyridinium Chloroaluminate Ionic Liquid as a New Heterogeneous Lewis Acid Catalyst for Knoevenagel Condensation. Journal of Chemical Research 36:7, pages 429-431.
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M. K. Pillai, S. Singh & S. B. Jonnalagadda. (2011) Solvent-free Knoevenagel condensation over iridium and platinum hydroxyapatites. Kinetics and Catalysis 52:4, pages 536-539.
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Blazej Duda, Sergey N. Tverdomed & Gerd-Volker Röschenthaler. (2010) Synthesis of 2-Perfluoroalkyl 4 H - and 2 H -Chromenylphosphonates Mediated by Amines and Phosphines . The Journal of Organic Chemistry 76:1, pages 71-79.
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Yan Zhang, Cuizhi Sun, Jun Liang & Zhicai Shang. (2010) Catalysis by L ‐Lysine: A Green Method for the Condensation of Aromatic Aldehydes with Acidic Methylene Compounds in Water at Room Temperature . Chinese Journal of Chemistry 28:11, pages 2255-2259.
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S. G. Zlotin, G. V. Kryshtal’, G. M. Zhdankina, A. V. Ignatenko, Ya. V. Burgart, V. I. Saloutin & O. N. Chupakhin. (2010) Synthesis of 2,6-bis(fluoroalkyl)-2,6-dihydroxytetrahydro-2H-pyran-3,5-dicarboxylates from aldehydes and fluorinated β-oxo esters in the presence of ionic liquid-K2CO3 as catalytic system. Russian Journal of Organic Chemistry 46:4, pages 468-473.
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Mercedes Boronat, Maria J. Climent, Avelino Corma, Sara Iborra, Raquel Montón & Maria J. Sabater. (2010) Bifunctional Acid–Base Ionic Liquid Organocatalysts with a Controlled Distance Between Acid and Base Sites. Chemistry – A European Journal 16:4, pages 1221-1231.
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An-Guo Ying, Li-Min Wang, Le-Le Wang, Xin-Zhi Chen & Wei-Dong Ye. (2010) Green and Efficient Knoevenagel Condensation Catalysed by a DBU Based ionic Liquid in Water. Journal of Chemical Research 34:1, pages 30-33.
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Mona Hosseini‐Sarvari, Hashem Sharghi & Samane Etemad. (2008) Nanocrystalline ZnO for Knoevenagel Condensation and Reduction of the Carbon,Carbon Double Bond in Conjugated Alkenes . Helvetica Chimica Acta 91:4, pages 715-724.
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M. Feroci, M. Orsini, G. Sotgiu & A. Inesi. (2008) The Knoevenagel reaction in electrochemically activated solvents. Electrochimica Acta 53:5, pages 2346-2354.
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Mona HOSSEINI‐SARVARI, Hashem SHARGHI & Samane ETEMAD. (2007) Solvent‐free Knoevenagel Condensations over TiO 2 . Chinese Journal of Chemistry 25:10, pages 1563-1567.
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Benjaram M. Reddy, Meghshyam K. Patil, Komateedi N. Rao & Gunugunuri K. Reddy. (2006) An easy-to-use heterogeneous promoted zirconia catalyst for Knoevenagel condensation in liquid phase under solvent-free conditions. Journal of Molecular Catalysis A: Chemical 258:1-2, pages 302-307.
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Nicholas D. P. Cosford & Pei Li Pauline. 2001. Encyclopedia of Reagents for Organic Synthesis. Encyclopedia of Reagents for Organic Synthesis.
Santosh S. Shindalkar, Balaji R. Madje, Rajkumar V. Hangarge, Pratap T. Patil, Mohan K. Dongare & Murlidhar S. Shingare. (2005) Borate Zirconia Mediated Knoevenagel Condensation Reaction in Water. Journal of the Korean Chemical Society 49:4, pages 377-380.
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E. S. Putilova, N. A. Troitskii & S. G. Zlotin. (2005) Reaction of aromatic aldehydes with β-dicarbonyl compounds in a catalytic system: Piperidinium acetate-1-butyl-3-methylimidazolium tetrafluoroborate ionic liquid. Russian Chemical Bulletin 54:5, pages 1233-1238.
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Jing-Yuan Liu, Yoeng-Jiunn Jang, Wen-Wei Lin, Ju-Tsung Liu & Ching-Fa Yao. (2003) Triethylaluminum- or Triethylborane-Induced Free Radical Reaction of Alkyl Iodides and α,β-Unsaturated Compounds. The Journal of Organic Chemistry 68:10, pages 4030-4038.
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Umberto Costantino, Massimo Curini, Francesca Montanari, Morena Nocchetti & Ornelio Rosati. (2003) Hydrotalcite-like compounds as catalysts in liquid phase organic synthesis. Journal of Molecular Catalysis A: Chemical 195:1-2, pages 245-252.
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O. ATTANASI, P. FILIPPONE & A. MEI. (2016) ChemInform Abstract: EFFECT OF METAL IONS IN ORGANIC SYNTHESIS. PART XVI. KNOEVENAGEL CONDENSATIONS OF ALDEHYDES AND TOSYLHYDRAZONES WITH 2,4‐PENTANEDIONE BY COPPER(II) CHLORIDE‐CATALYZED REACTION. Chemischer Informationsdienst 15:36.
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