Publication Cover
Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 35, 2005 - Issue 5
487
Views
62
CrossRef citations to date
0
Altmetric
Original Articles

Organic Reactions in Ionic Liquids: Ionic Liquids Ethylammonium Nitrate Promoted Knoevenagel Condensation of Aromatic Aldehydes with Active Methylene Compounds

, , &
Pages 739-744 | Received 19 Aug 2004, Published online: 20 Aug 2006

Keep up to date with the latest research on this topic with citation updates for this article.

Read on this site (8)

Sanhu Zhao, Dan Meng, Lingling Wei, Yongsheng Qiao & Fugui Xi. (2019) Novel DBU-based hydroxyl ionic liquid for efficient Knoevenagel reaction in water. Green Chemistry Letters and Reviews 12:3, pages 271-277.
Read now
G. Thirupathi, M. Venkatanarayana, P. K. Dubey & Y. Bharathi Kumari. (2013) Facile and Green Syntheses of 2-(N-Methylindole-3-carbonyl)-3-(N-methylpyrrol-2-yl)acrylonitriles and a Study of Their Antimicrobial Activities. Synthetic Communications 43:22, pages 2967-2979.
Read now
Ying Han, Er-Yan Xia, Qun Wu, Jing Sun & Chao-Guo Yan. (2013) Synthesis of Ammonium 3,5-Dicyano-4-aryl-2,6-pyridinedionates with One-Pot Reaction of Aromatic Aldehydes, Amines, and Cyanoacetamide. Synthetic Communications 43:10, pages 1413-1424.
Read now
JagirS. Sandhu. (2011) Recent advances in ionic liquids: green unconventional solvents of this century: part I. Green Chemistry Letters and Reviews 4:4, pages 289-310.
Read now
Qing Liu & Yinfeng Han. (2011) Knoevenagel Condensation Catalyzed by Sodium Silicate Under Solvent-Free Conditions. Phosphorus, Sulfur, and Silicon and the Related Elements 186:10, pages 2033-2037.
Read now
AbdolR. Hajipour & Fatemeh Rafiee. (2010) Acidic Bronsted Ionic Liquids. Organic Preparations and Procedures International 42:4, pages 285-362.
Read now
Daryoush Tahmassebi, LeviJ. A. Wilson & JerodM. Kieser. (2009) Knoevenagel Condensation of Aldehydes with Meldrum's Acid in Ionic Liquids. Synthetic Communications 39:14, pages 2605-2613.
Read now
Jicheng Zhang, Tao Jiang, Buxing Han, Anlian Zhu & Xiumin Ma. (2006) Knoevenagel Condensation Catalyzed by 1,1,3,3‐Tetramethylguanidium Lactate. Synthetic Communications 36:22, pages 3305-3317.
Read now

Articles from other publishers (54)

Manpreet Singh, Harjinder Singh, Omish Sethi, Ashwani Kumar Sood & Tejwant Singh Kang. (2022) Investigating the thermodynamic properties and interactional behaviour of a protic room temperature ionic liquid in binary mixtures with ethylene glycol derivatives at different temperatures. Journal of Molecular Liquids 367, pages 120410.
Crossref
Roli Mishra, Satyendra Mishra, Snehkrishn A Chaubey & Yash B Barot. 2021. Handbook of Greener Synthesis of Nanomaterials and Compounds. Handbook of Greener Synthesis of Nanomaterials and Compounds 359 404 .
Jie Jack LiJie Jack Li. 2021. Name Reactions. Name Reactions 294 297 .
Yuyan Deng, Jia Yao & Haoran Li. (2020) Effects of ionicity and chain structure on the physicochemical properties of protic ionic liquids. AIChE Journal 66:10.
Crossref
S. Bentahar, M. Ait Taleb, A. Sabour, A. Dbik, M. El Khomri, N. El Messaoudi & A. Lacherai. (2020) The Modified Clay as a New and Eco-Friendly Catalyst for the Knoevenagel Reaction. Russian Journal of Applied Chemistry 93:9, pages 1438-1444.
Crossref
Chun Li, Mengna Wang, Xunhua Lu, Ling Zhang, Jian Jiang & Lin Zhang. (2020) Reusable Brønsted Acidic Ionic Liquid Efficiently Catalyzed N -Formylation and N -Acylation of Amines . ACS Sustainable Chemistry & Engineering 8:11, pages 4353-4361.
Crossref
Sathish Dasari & Bhabani S. Mallik. (2018) Nondiffusive Rotational Jump Dynamics in Ethyl Ammonium Nitrate. The Journal of Physical Chemistry B 122:42, pages 9738-9746.
Crossref
Bin Xie, Yingjie Xu, Xiaochen Tang, Hegang Shu, Tingting Chen & Xiao Zhu. (2018) Comparison of the alkalinity of hydroxypyridine anion-based protic ionic liquids and their catalytic performance for Knoevenagel reaction: The effect of the type of cation and the position of nitrogen atom of anion. Journal of Molecular Liquids 268, pages 610-616.
Crossref
S.M. Hosseini, S. Aparicio, M.M. Alavianmehr & R. Khalifeh. (2018) On the volumetric properties of 2-hydroxy ethylammonium formate ionic liquid under high-pressures: Measurement and molecular dynamics. Journal of Molecular Liquids 266, pages 751-761.
Crossref
João A. Sarabando, Paulo J.M. Magano, Abel G.M. Ferreira, Jaime B. Santos, Pedro J. Carvalho, Silvana Mattedi & Isabel M.A. Fonseca. (2018) Influence of temperature and pressure on the density and speed of sound of 2-hydroxyethylammonium propionate ionic liquid. The Journal of Chemical Thermodynamics 122, pages 183-193.
Crossref
M. S. Gruzdev, M. A. Krestyaninov, E. N. Krylov, L. E. Shmukler & L. P. Safonova. (2018) Possibility of Protic Ionic Liquids Formation From Triethanolamine with Sulfonamides. The Journal of Physical Chemistry B 122:25, pages 6586-6594.
Crossref
S.M. Hosseini, M.M. Alavianmehr, A. Gutiérrez, R. Khalifeh, J. Moghadasi & S. Aparicio. (2018) On the properties and structure of 2-hydroxyethylammonium formate ionic liquid. Journal of Molecular Liquids 249, pages 233-244.
Crossref
Razieh Maleki, Eskandar Kolvari, Mehdi Salehi & Nadiya Koukabi. (2017) Fe 3 O 4 –cysteamine hydrochloride magnetic nanoparticles: New, efficient and recoverable nanocatalyst for Knoevenagel condensation reaction . Applied Organometallic Chemistry 31:11.
Crossref
Matías A. Crosio, Juana J. Silber, R. Darío Falcone & N. Mariano Correa. (2017) On the design of a versatile ionic liquid, AOBH-DEHP, which can be used as a new molecular probe to investigate supramolecular assemblies. Dyes and Pigments 138, pages 68-76.
Crossref
Masoumeh Abedini, Farhad Shirini, Javad Mohammad-Alinejad Omran, Mohadeseh Seddighi & Omid Goli-Jolodar. (2015) Succinimidinium N-sulfonic acid hydrogen sulfate as an efficient ionic liquid catalyst for the synthesis of 5-arylmethylene-pyrimidine-2,4,6-trione and pyrano[2,3-d]pyrimidinone derivatives. Research on Chemical Intermediates 42:5, pages 4443-4458.
Crossref
Matías A. Crosio, N. Mariano Correa, Juana J. Silber & R. Darío Falcone. (2016) A protic ionic liquid, when entrapped in cationic reverse micelles, can be used as a suitable solvent for a bimolecular nucleophilic substitution reaction. Org. Biomol. Chem. 14:11, pages 3170-3177.
Crossref
Lakshmi Narayanan Jayalakshmi, Ayyanar Karuppasamy, Kesavan Stalindurai, Ramar Sivaramakarthikeyan, Vellasamy Devadoss & Chennan Ramalingan. (2015) Straightforward syntheses of nitriles, acrylates, and acrylamides in aqueous propan-1,2-diol: a catalyst free and waste free methodology. Tetrahedron Letters 56:28, pages 4207-4210.
Crossref
Arijit Bhattacharjee, João A. P. Coutinho, Mara G. Freire & Pedro J. Carvalho. (2015) Thermophysical Properties of Two Ammonium-Based Protic Ionic Liquids. Journal of Solution Chemistry 44:3-4, pages 703-717.
Crossref
Anguo Ying, Limin Wang, Fangli Qiu, Huanan Hu & Jianguo Yang. (2015) Magnetic nanoparticle supported amine: An efficient and environmental benign catalyst for versatile Knoevenagel condensation under ultrasound irradiation. Comptes Rendus Chimie 18:2, pages 223-232.
Crossref
P. Praveen Kumar, Y. Dathu Reddy, Ch. Venkata Ramana Reddy, B. Rama Devi & P.K. Dubey. (2014) One pot, three-component synthesis of novel 3,4-dihydrophthalazin-2(1H)-yl-4-phenyl-4H-pyrans. Tetrahedron Letters 55:14, pages 2177-2182.
Crossref
Shuo Liu, Yuxiang Ni, Wenjing Wei, Fangli Qiu, Songlin Xu & Anguo Ying. (2014) Choline Chloride and Urea Based Eutectic Solvents: Effective Catalytic Systems for the Knoevenagel Condensation Reactions of Substituted Acetonitriles. Journal of Chemical Research 38:3, pages 186-188.
Crossref
Rammohan Pal & Taradas Sarkar. (2014) Visible Light Induced Knoevenagel Condensation Catalyzed by Starfruit Juice of <i>Averrhoa carambola</i>. International Journal of Organic Chemistry 04:02, pages 106-115.
Crossref
Nieves M.C. Talavera-Prieto, Abel G.M. Ferreira, Pedro N. Simões, Pedro J. Carvalho, Silvana Mattedi & João A.P. Coutinho. (2014) Thermophysical characterization of N-methyl-2-hydroxyethylammonium carboxilate ionic liquids. The Journal of Chemical Thermodynamics 68, pages 221-234.
Crossref
Jie Jack LiJie Jack Li. 2014. Name Reactions. Name Reactions 344 346 .
Ya‐Qin Yu & Zhong‐Liang Wang. (2012) A Simple, Efficient and Green Procedure for Knoevenagel Condensation in Water or under Solvent‐free Conditions. Journal of the Chinese Chemical Society 60:3, pages 288-292.
Crossref
Da-Zhen Xu, Sen Shi & Yongmei Wang. (2013) Polystyrene-immobilized DABCO as a highly efficient and recyclable organocatalyst for the Knoevenagel condensation reaction. RSC Advances 3:45, pages 23075.
Crossref
Sanhu Zhao, Xiaoju Wang & Liwei Zhang. (2013) Rapid and efficient Knoevenagel condensation catalyzed by a novel protic ionic liquid under ultrasonic irradiation. RSC Advances 3:29, pages 11691.
Crossref
Cinzia Chiappe & Sunita Rajamani. (2011) Structural Effects on the Physico‐Chemical and Catalytic Properties of Acidic Ionic Liquids: An Overview. European Journal of Organic Chemistry 2011:28, pages 5517-5539.
Crossref
Roozbeh Javad Kalbasi, Majid Kolahdoozan & Sedigheh Mozafari Vanani. (2011) Preparation, characterization and catalyst application of ternary interpenetrating networks of poly 4-methyl vinyl pyridinium hydroxide–SiO2–Al2O3. Journal of Solid State Chemistry 184:8, pages 2009-2016.
Crossref
Sumit Ghosh. (2011) Comparative studies on brij reverse micelles prepared in benzene/surfactant/ethylammonium nitrate systems: Effect of head group size and polarity of the hydrocarbon chain. Journal of Colloid and Interface Science 360:2, pages 672-680.
Crossref
Jason P. Hallett & Tom Welton. (2011) Room-Temperature Ionic Liquids: Solvents for Synthesis and Catalysis. 2. Chemical Reviews 111:5, pages 3508-3576.
Crossref
Qing Liu, Hongmei Ai & Zhen Li. (2011) Potassium sorbate as an efficient and green catalyst for Knoevenagel condensation. Ultrasonics Sonochemistry 18:2, pages 477-479.
Crossref
Roozbeh Javad Kalbasi, Majid Kolahdoozan & Mahsa Rezaei. (2011) Synthesis and characterization of PVAm/SBA-15 as a novel organic–inorganic hybrid basic catalyst. Materials Chemistry and Physics 125:3, pages 784-790.
Crossref
Roozbeh Javad Kalbasi, Majid Kolahdoozan, Ahmadreza Massah & Keinaz Shahabian. (2010) Synthesis, Characterization and Application of Poly(4-Methyl Vinylpyridinium Hydroxide)/SBA-15 Composite as a Highly Active Heterogeneous Basic Catalyst for the Knoevenagel Reaction. Bulletin of the Korean Chemical Society 31:9, pages 2618-2626.
Crossref
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.
Crossref
Da-Zhen Xu, Yingjun Liu, Sen Shi & Yongmei Wang. (2010) A simple, efficient and green procedure for Knoevenagel condensation catalyzed by [C4dabco][BF4] ionic liquid in water. Green Chemistry 12:3, pages 514.
Crossref
Marie-Christine Scherrmann. 2010. Carbohydrates in Sustainable Development II. Carbohydrates in Sustainable Development II 1 18 .
Swapnil R. Sarda, Jagpal D. Kale, Sunil K. Wasmatkar, Vijay S. Kadam, Pravin G. Ingole, Wamanrao N. Jadhav & Rajendra P. Pawar. (2009) An efficient protocol for the synthesis of 2-amino-4,6-diphenylpyridine-3-carbonitrile using ionic liquid ethylammonium nitrate. Molecular Diversity 13:4, pages 545-549.
Crossref
Claudia G. Adam, Graciela G. Fortunato & Pedro M. Mancini. (2009) Nucleophilic and acid catalyst behavior of a protic ionic liquid in a molecular reaction media. Part 1. Journal of Physical Organic Chemistry 22:5, pages 460-465.
Crossref
Manas Chakrabarty, Ratna Mukherjee, Shiho Arima & Yoshihiro Harigaya. (2009) Reaction of Isatins with Active Methylene Compounds on Neutral Alumina: Formation of Knoevenagel Condensates and Other Interesting Products. HETEROCYCLES 78:1, pages 139.
Crossref
Montserrat Trilla, Roser Pleixats, Michel Wong Chi Man & Catherine Bied. (2009) Organic–inorganic hybrid silica materials containing imidazolium and dihydroimidazolium salts as recyclable organocatalysts for Knoevenagel condensations. Green Chemistry 11:11, pages 1815.
Crossref
Jie Jack LiJie Jack Li. 2009. Name Reactions. Name Reactions 315 316 .
Yang Liu, Jun Liang, Xiu Hong Liu, Ji Cai Fan & Zhi Cai Shang. (2008) Polyethylene glycol (PEG) as a benign solvent for Knoevenagel condensation. Chinese Chemical Letters 19:9, pages 1043-1046.
Crossref
Chuan Zhao, Geoff Burrell, Angel A. J. Torriero, Frances Separovic, Noel F. Dunlop, Douglas R. MacFarlane & Alan M. Bond. (2008) Electrochemistry of Room Temperature Protic Ionic Liquids. The Journal of Physical Chemistry B 112:23, pages 6923-6936.
Crossref
Caibo Yue, Aiqin Mao, Yunyang Wei & Minjie Lü. (2008) Knoevenagel condensation reaction catalyzed by task-specific ionic liquid under solvent-free conditions. Catalysis Communications 9:7, pages 1571-1574.
Crossref
Debabrata Seth, Souravi Sarkar & Nilmoni Sarkar. (2008) Solvent and Rotational Relaxation of Coumarin 153 in a Protic Ionic Liquid Dimethylethanolammonium Formate. The Journal of Physical Chemistry B 112:9, pages 2629-2636.
Crossref
Hui Kang, Yi Hu, He Huang & Ping Wei. (2008) CONDENSATION OF 1,3-CYCLOHEXANEDIONE WITH AROMATIC ALDEHYDES CATALYZED BY ACIDIC IONIC LIQUIDS. Heterocyclic Communications 14:4.
Crossref
Tamar L. Greaves & Calum J. Drummond. (2007) Protic Ionic Liquids:  Properties and Applications. Chemical Reviews 108:1, pages 206-237.
Crossref
E. Kleinpeter & M. Sefkow. 2008. Comprehensive Heterocyclic Chemistry III. Comprehensive Heterocyclic Chemistry III 739 856 .
Kang Hyun Park, Il Gu Jung, Young Keun Chung & Jin Wook Han. (2007) Activation of CCl Bonds in Chloroalkanes by Nickel Oxide Nanoparticles: Formation of Tetrasubstituted Ammonium Salts from Tertiary Amines. Advanced Synthesis & Catalysis 349:3, pages 411-416.
Crossref
Tamar L. Greaves, Asoka Weerawardena, Celesta Fong, Irena Krodkiewska & Calum J. Drummond. (2006) Protic Ionic Liquids:  Solvents with Tunable Phase Behavior and Physicochemical Properties. The Journal of Physical Chemistry B 110:45, pages 22479-22487.
Crossref
David C. Forbes, Amanda M. Law & Doug W. Morrison. (2006) The Knoevenagel reaction: analysis and recycling of the ionic liquid medium. Tetrahedron Letters 47:11, pages 1699-1703.
Crossref
. 2006. Name Reactions. Name Reactions 329 330 .
Yi Hu, Jue Chen, Zhang‐Gao Le & Qin‐Guo Zheng. (2005) Organic Reactions in Ionic Liquids: Ionic Liquids Ethylammonium Nitrate Promoted Knoevenagel Condensation of Aromatic Aldehydes with Active Methylene Compounds.. ChemInform 36:48.
Crossref

Reprints and Corporate Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

To request a reprint or corporate permissions for this article, please click on the relevant link below:

Academic Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

Obtain permissions instantly via Rightslink by clicking on the button below:

If you are unable to obtain permissions via Rightslink, please complete and submit this Permissions form. For more information, please visit our Permissions help page.