Knoevenagel reaction promoted by functional ionic liquids with primary and tertiary amines

References

• Zhao, S.; Wang, X.; Zhang, L. Rapid and Efficient Knoevenagel Condensation Catalyzed by a Novel Protic Ionic Liquid Under Ultrasonic Irradiation. RSC Adv. 2013, 3, 11691–11696.
   Web of Science ®Google Scholar
• Beurden, K.; Koning, S.; Molendijk, D.; Schijndel, J. The Knoevenagel Reaction: A Review of the Unfinished Treasure Map to Forming Carbon-Carbon Bonds. Green Chem. Lett. Rev. 2020, 13, 349–364.
   Web of Science ®Google Scholar
• Rao, P.S.; Venkatratnam, R.V. Zinc Chloride as a New Catalyst for Knoevenagel Condensation. Tetrahedron Lett. 1991, 32, 5821–5822.
   Web of Science ®Google Scholar
• Attansi, O.; Fillippone, P.; Mei, A. 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. Synth. Commun. 1983, 13, 1203–1208.
   Web of Science ®Google Scholar
• Ogiwara, Y.; Takahashi, K.; Kitazawa, T.; Saka, N. Indium(III)-Catalyzed Knoevenagel Condensation of Aldehydes and Activated Methylenes Using Acetic Anhydride as a Promoter. J. Org. Chem. 2015, 80, 3101–3110.
   PubMed Web of Science ®Google Scholar
• Narsaiah, A.V.; Nagaiah, K. An Efficient Knoevenagel Condensation Catalyzed by LaCl3·7H2O in Heterogeneous Medium. Synth. Commun. 2003, 33, 3825–3832.
   Web of Science ®Google Scholar
• Cai, M.; Wang, X.; Fang, Y.; Chen, Y.; Dai, L. Robust Mg(Ca)Zr-Doped Acid-Base Bifunctional Mesoporous Silica and Their Applications in the Deacetalization-Knoevenagel Reaction. Inorg. Chem. 2021, 60, 8924–8935.
   PubMed Web of Science ®Google Scholar
• Liu, D.; Hou, S.; Shu, Y.; Zhao, J.; Wang, L.; Zhang, P. Mechanochemical NaCl-Mediated Synthesis of Porous CuxMo1–xOy Catalyst for Knoevenagel Condensation. Ind. Eng. Chem. Res. 2021, 60, 17778–17785.
   Web of Science ®Google Scholar
• Kalantari, F.; Rezayati, S.; Ramazani, A.; Aghahosseini, H.; Ślepokura, K.; Lis, T. Proline-Cu Complex Based 1,3,5-Triazine Coated on Fe3O4 Magnetic Nanoparticles: A Nanocatalyst for the Knoevenagel Condensation of Aldehyde with Malononitrile. ACS Applied Nano Materials 2022, 5, 1783–1797.
   Google Scholar
• Zhang, T.; Chen, H.; Liu, S.; Lv, H.; Zhang, X.; Li, Q. Highly Robust {Ln4}-Organic Frameworks (Ln = Ho, Yb) for Excellent Catalytic Performance on Cycloaddition Reaction of Epoxides with CO2 and Knoevenagel Condensation. ACS Catal. 2021, 11, 14916–14925.
   Web of Science ®Google Scholar
• Varnaseri, N.; Rouhani, F.; Ramazani, A.; Morsali, A. Size and Function Influence Study on Enhanced Catalytic Performance of a Cooperative MOF for Mild, Green and Fast C-C Bond Formation. Dalton Trans. 2020, 49, 3234–3242.
   PubMed Web of Science ®Google Scholar
• Kalantari, F.; Ramazani, A.; Heravi, R.P.M.; Aghahosseini, H.; Ślepokura, K. Magnetic Nanoparticles Functionalized with Copper Hydroxyproline Complexes as an Efficient, Recoverable, and Recyclable Nanocatalyst: Synthesis and Its Catalytic Application in a Tandem Knoevenagel–Michael Cyclocondensation Reaction. Inorg. Chem. 2021, 60, 15010–15023.
   PubMed Web of Science ®Google Scholar
• Sadgar, A.L.; Deore, T.S.; Jayaram, R.V. Pickering Interfacial Catalysis-Knoevenagel Condensation in Magnesium Oxide-Stabilized Pickering Emulsion. ACS Omega 2020, 5, 12224–12235.
   PubMed Web of Science ®Google Scholar
• Tavakolian, M.; Najafpour, M.M. Molybdenum Carbide as an Efficient and Durable Catalyst for Aqueous Knoevenagel Condensation. New J. Chem. 2019, 43, 16437–16440.
   Web of Science ®Google Scholar
• Murase, T.; Nishijima, Y.; Fujita, M. Cage-Catalyzed Knoevenagel Condensation Under Neutral Conditions in Water. J. Am. Chem. Soc. 2012, 134, 162–164.
   PubMed Web of Science ®Google Scholar
• Seckler, D.; Dea, C.M.; Rios, E.A.M.; de Godoi, M.; Rampon, D.S.; D’Oca, M.G.M.; D’Oca, C.D.R.M. Rice Straw Ash Extract/Glycerol: An Efficient Sustainable Approach for Knoevenagel Condensation. New J. Chem. 2022, 46, 4570–4578.
   Web of Science ®Google Scholar
• Hirayama, Y.; Kanomata, K.; Hatakeyama, M.; Kitaoka, T. Chitosan Nanofiber-Catalyzed Highly Selective Knoevenagel Condensation in Aqueous Methanol. RSC Adv. 2020, 10, 26771–26776.
   PubMed Web of Science ®Google Scholar
• Takakura, R.; Koyama, K.; Kuwata, M.; Yamada, T.; Sajiki, H.; Sawama, Y. Hydroquinone and Benzoquinone-Catalyzed Aqueous Knoevenagel Condensation. Org. Biomol. Chem. 2020, 18, 6594–6597.
   PubMed Web of Science ®Google Scholar
• Jung, K.; Kim, S.; Choi, S.; Kim, I.; Han, G. Development of a DABCO-Succinic Acid Based Catalytic System for the Aza-Michael Addition and Aza-Michael/Knoevenagel Tandem Reaction of Thiazolidine-2, 4-Dione to Electron Deficient Alkenes. J. Org. Chem. 2021, 86, 16785–16794.
   PubMed Web of Science ®Google Scholar
• Li, J.; He, D.; Lin, Z.; Cen, L.; Wu, W.; Jiang, H. NHC-Palladium-Catalyzed Ionic Liquid-Accelerated Regioselective Oxyarylation of Alkynes with Diaryl Ethers. Green Chem. 2022, 24, 1983–1988.
   Web of Science ®Google Scholar
• Li, Y.Q.; Xu, X.M.; Zhou, M.Y. n-Butyl Pyridinium Nitrate as a Reusable Ionic Liquid Medium for Knoevenagel Condensation. Chin. Chem. Lett. 2003, 14, 448–450.
   Web of Science ®Google Scholar
• Morison, D.W.; Forbes, D.C.; Davis, J.H. Base-Promoted Reactions in Ionic Liquid Solvents. The Knoevenagel and Robinson Annulation Reactions. Tetrahedron Lett. 2001, 42, 6053–6055.
   Web of Science ®Google Scholar
• Wang, Y.; Shang, Z.C.; Fan, T.X.; Chen, X. Synthetic and Theoretical Study on Proline-Catalyzed Knoevenagel Condensation in Ionic Liquid. J. Mol. Catal. A 2006, 253, 212–221.
   Web of Science ®Google Scholar
• Siddiqui, Z.N.; Khan, K. [Et3NH] [HSO4]-Catalyzed Efficient, Eco-Friendly, and Sustainable Synthesis of Quinoline Derivatives via Knoevenagel Condensation. ACS Sustainable Chem. Eng. 2014, 2, 1187–1194.
   Web of Science ®Google Scholar
• Li, J.; Sun, H.; Cai, X.-C.; Dai, L.-Y. Application of Basic Ionic Liquid [Bmim]OH to Knoevenagel and Perkin Reactions. Chin. J. Org. Chem. 2007, 27, 1296–1299.
   Web of Science ®Google Scholar
• Xu, D.-Z.; Liu, Y.; Shi, S.; Wang, Y. A Simple, Efficient and Green Procedure for Knoevenagel Condensation Catalyzed by [C4dabco][BF4] Ionic Liquid in Water. Green Chem. 2010, 12, 514–517.
   Web of Science ®Google Scholar
• Yang, C.; Su, W.-Q.; Xu, D.-Z. Ionic Liquid [Dabco-H][AcO] as a Highly Efficient and Recyclable Catalyst for the Synthesis of Various Bisenol Derivatives via Domino Knoevenagel-Michael Reaction in Aqueous Media. RSC Adv. 2016, 6, 99656–99663.
   Web of Science ®Google Scholar
• Ying, A.-G.; Liu, L.; Wu, G.-F.; Chen, X.-Z.; Ye, W.-D.; Chen, J.-H.; Zhang, K.-Y. Knoevenagel Condensation Catalyzed by DBU Brönsted Ionic Liquid Without Solvent. Chem. Res. Chin. Univ. 2009, 25, 876–881.
   Web of Science ®Google Scholar
• Ying, A.; Ni, Y.; Xu, S.; Liu, S.; Yang, J.; Li, R. Novel DABCO Based Ionic Liquids: Green and Efficient Catalysts with Dual Catalytic Roles for Aqueous Knoevenagel Condensation. Ind. Eng. Chem. Res. 2014, 53, 5678–5682.
   Web of Science ®Google Scholar
• Garrabou, X.; Wicky, B.I.M.; Hilvert, D. Fast Knoevenagel Condensations Catalyzed by an Artificial Schiff-Base-Forming Enzyme. J. Am. Chem. Soc. 2016, 138, 6972–6974.
   PubMed Web of Science ®Google Scholar
• Islam, M.J.; Kumer, A.; Sarker, M.N.; Paul, S. The Activity of Alkyl Groups in Morpholinium Cation on Chemical Reactivity, and Biological Properties of Morpholinium Tetrafluroborate Ionic Liquid Using the DFT Method. Chem. Methodol. 2020, 4, 130–142.
   Google Scholar
• Sajjadifar, S.; Amini, I.; Habibzadeh, S.; Mansouri, G.; Ebadi, E. Acidic Ionic Liquid Based Silica-Coated Fe3O4 Nanoparticles as a New Nanomagnetic Catalyst for Preparation of Aryl and Heteroaryl Thiocyanates. Chem. Methodol. 2020, 4, 624–635.
   Google Scholar
• Zhu, H.-P.; Yang, F.; Tang, J.; He, M.-Y. Brønsted Acidic Ionic Liquid 1-Methylimidazolium Tetrafluoroborate: A Green Catalyst and Recyclable Medium for Esterification. Green Chem. 2003, 5, 38–39.
   Web of Science ®Google Scholar
• Zhang, L.; Xian, M.; He, Y.; Li, L.; Yang, J.; Yu, S.; Xu, X. A Brønsted Acidic Ionic Liquid as an Efficient and Environmentally Benign Catalyst for Biodiesel Synthesis from Free Fatty Acids and Alcohols. Biores. Technol. 2009, 100 (19), 4368–4373.
   PubMed Web of Science ®Google Scholar
• Azizi, N.; Abdoli-Senejani, M.; Abbasi, F. An Efficient Brønsted–Lewis Acidic Ionic Liquid Catalyzed Tetrahydropyranylation of Alcohols. Tetrahedron Lett. 2016, 57, 5009–5011.
   Web of Science ®Google Scholar
• Azizi, N.; Shirdel, F. Task Specific Dicationic Acidic Ionic Liquids Catalyzed Efficient and Rapid Synthesis of Benzoxanthenones Derivatives. J. Mol. Liq. 2016, 222, 783–787.
   Web of Science ®Google Scholar
• Cole, A.C.; Jensen, J.L.; Ntai, I.; Tran, K.L.T.; Weaver, K.J.; Forbes, D.C.; Davis, J.H. Novel Brønsted Acidic Ionic Liquids and Their Use as Dual Solvent-Catalysts. J. Am. Chem. Soc. 2002, 124, 5962–5963.
   PubMed Web of Science ®Google Scholar
• Amarasekara, A.S. Acidic Ionic Liquids. Chem. Rev. 2016, 116, 6133–6183.
   PubMed Web of Science ®Google Scholar
• Abbott, A.P.; Capper, G.; Davies, D.L.; Munro, H.L.; Rasheed, R.K.; Tambyrajah, V. Preparation of Novel, Moisture-Stable, Lewis-Acidic Ionic Liquids Containing Quaternary Ammonium Salts with Functional Side Chains. Chem. Commun. 2001, 1, 2010–2011.
   Google Scholar
• Ding, J.; Wang, P.; He, Y.; Cheng, L.; Li, X.; Fang, C.; Li, H.; Wan, H.; Guan, G. Porous Sulfonyl Binuclear Carbonate Poly(Ionic Liquid)s for One-pot Fixation of Diluted CO2 Into Dimethyl Carbonate. Appl. Catal. B Environ. 2023, 324, 122278.
   Web of Science ®Google Scholar
• Ventura, S.P.M.; Silva, F.A.; Quental, M.V.; Mondal, D.; Freire, M.G.; Coutinho, J.A.P. Ionic-Liquid-Mediated Extraction and Separation Processes for Bioactive Compounds: Past,: Present, and Future Trends. Chem. Rev. 2017, 117, 6984–7052.
   PubMed Web of Science ®Google Scholar
• Aflatoonian, M.R.; Tajik, S.; Aflatoonian, B.; Shoaie, I.S.; Sheikhshoaie, M.; Beitollahi, H. Copper Oxide, Ionic Liquid and Mn(III) Salen Modified Carbon Paste Electrode as Selective Electrochemical Sensor for Determination of Droxidopa in the Presence of Carbidopa. Eurasian Chem. Commun. 2020, 2, 387–397.
   Google Scholar
• Saghiri, S.; Ebrahimi, M.; Bozorgmehr, M. Electrochemical Amplified Sensor with MgO Nanoparticle and Ionic Liquid: A Powerful Strategy for Methyldopa Analysis. Chem. Methodol. 2021, 5, 234–239.
   Google Scholar
• Trujillo-Rodríguez, M.J.; Nan, H.; Varona, M.; Emaus, M.N.; Souza, I.D.; Anderson, J.L. Advances of Ionic Liquids in Analytical Chemistry. Anal. Chem. 2019, 91, 505–531.
   PubMed Web of Science ®Google Scholar
• Egorova, K.S.; Gordeev, E.G.; Ananikov, V.P. Biological Activity of Ionic Liquids and Their Application in Pharmaceutics and Medicine. Chem. Rev. 2017, 117, 7132–7189.
   PubMed Web of Science ®Google Scholar
• Jia, X.; Wang, D.; Zhao, S. Preparation of Deep Eutectic Solvents and Its Application in Morita-Baylis-Hillman Reaction. Chem. Res. Appl. 2021, 33, 2330–2338.
   Google Scholar
• Yang, Y.; Yao, H.-F.; Xi, F.-G.; Gao, E.-Q. Amino-Functionalized Zr(IV) Metal-Organic Framework as Bifunctional Acid-Base Catalyst for Knoevenagel Condensation. J. Mol. Catal. A: Chem. 2014, 390, 198–205.
   Web of Science ®Google Scholar
• Zhang, X.; He, X.; Zhao, S. Preparation of a Novel Fe3O4@SiO2@Propyl@DBU Magnetic Core–Shell Nanocatalyst for Knoevenagel Reaction in Aqueous Medium. Green Chem. Lett. Rev. 2021, 14, 85–98.
   Web of Science ®Google Scholar
• Song, A.; Wang, X.; Lam, K.S. A Convenient Synthesis of Coumarin-3-Carboxylic Acids via Knoevenagel Condensation of Meldrum'S Acid with Ortho-Hydroxyaryl Aldehydes or Ketones. Tetrahedron Lett. 2003, 44, 1755–1758.
   Web of Science ®Google Scholar
• Popp, F.D. Notes-Synthesis of 3-Hydroxypyridines. I. Condensation of Aromatic Aldehydes with Ethyl Cyanoacetate. J. Org. Chem. 1960, 25, 646–647.
   Web of Science ®Google Scholar
• Li, G.; Xiao, J.; Zhang, W. Knoevenagel Condensation Catalyzed by a Tertiary-Amine Functionalized Polyacrylonitrile Fiber. Green Chem. 2011, 13, 1828–1836.
   Web of Science ®Google Scholar
• Yue, C.; Mao, A.; Wei, Y.; Lue, M. Knoevenagel Condensation Reaction Catalyzed by Task-Specific Ionic Liquid Under Solvent Free Conditions. Catal. Commun. 2008, 9, 1571–1574.
   Web of Science ®Google Scholar
• Ying, A.-G.; Wang, L.-M.; Wang, L.-L.; Chen, X.-Z.; Ye, W.-D. Green and Efficient Knoevenagel Condensation Catalyzed by a DBU Based Ionic Liquid in Water. J. Chem. Res. 2010, 1, 30–33.
   Google Scholar
• Zhang, J.; Jiang, T.; Han, B.; Zhu, A.; Ma, X. Knoevenagel Condensation Catalyzed by 1,1,3,3-Tetramethylguanidium Lactate. Synth. Commun. 2006, 36, 3305–3317.
   Web of Science ®Google Scholar
• Ren, Z.; Cao, W.; Tong, W. The Knoevenagel Condensation Reaction of Aromatic Aldehydes with Malononitrile by Grinding in the Absence of Solvents and Catalysts. Synth. Commun. 2002, 32, 3475–3479.
   Web of Science ®Google Scholar
• Zhao, S.; He, M.; Guo, Z.; Zhou, N.; Wang, D.; Li, J.; Zhang, L. [HyEtPy]Cl-H2O: An Efficient and Versatile Solvent System for the DABCO-Catalyzed Morita-Baylis-Hillman Reaction. RSC Adv. 2015, 5, 32839–32845.
   Google Scholar
• Zhao, S.; Xu, X.; Zheng, L.; Liu, H. An Efficient Ultrasonic-Assisted Synthesis of Imidazolium and Pyridinium Salts Based on the Zincke Reaction. Ultrason. Sonochem. 2010, 17, 685–689.
   PubMed Web of Science ®Google Scholar
• Parvin, M.N.; Jin, H.; Ansari, M.B.; Oh, S.-M.; Park, S.-E. Imidazolium Chloride Immobilized SBA-15 as a Heterogenized Organocatalyst for Solvent Free Knoevenagel Condensation Using Microwave. Appl. Catal. A 2012, 413–414, 205–212.
   Web of Science ®Google Scholar
• Postole, G.; Chowdhury, B.; Karmakar, B.; Pinki, K.; Banerji, J.; Auroux, A. Knoevenagel Condensation Reaction Over Acid–Base Bifunctional Nanocrystalline CexZr1−xO2 Solid Solutions. J. Catal. 2010, 269, 110–121.
   Web of Science ®Google Scholar
• Ansari, M.B.; Jin, H.; Parvin, M.N.; Park, S.-E. Mesoporous Carbon Nitride as a Metal-Free Base Catalyst in the Microwave Assisted Knoevenagel Condensation of Ethylcyanoacetate with Aromatic Aldehydes. Catal. Today 2012, 185, 211–216.
   Web of Science ®Google Scholar
• Liu, Y.; Liang, J.; Liu, X.H.; Fan, J.C.; Shang, Z.C. Polyethylene Glycol (PEG) as a Benign Solvent for Knoevenagel Condensation. Chin. Chem. Lett. 2008, 19, 1043–1046.
   Web of Science ®Google Scholar
• Boroujeni, K.P.; Jafarinasa, M. Polystyrene-Supported Chloroaluminate Ionic Liquid as a New Heterogeneous Lewis Acid Catalyst for Knoevenagel Condensation. Chin. Chem. Lett. 2012, 23, 1067–1070.
   Web of Science ®Google Scholar
• Kumar, A.; Dewan, M.; Saxena, A.; De, A.; Mozumdar, S. Knoevenagel Condensation Catalyzed by Chemo-Selective Ni-Nanoparticles in Neutral Medium. Catal. Commun. 2010, 11, 679–683.
   Web of Science ®Google Scholar
• Sugahara, K.; Kimura, T.; Kamata, K.; Yamaguchi, K.; Mizuno, N. A Highly Negatively Charged γ-Keggin Germanodecatungstate Efficient for Knoevenagel Condensation. Chem. Commun. 2012, 48, 8422–8424.
   PubMed Web of Science ®Google Scholar
• Elhamifar, D.; Kazempoor, S.; Karimi, B. Amine-Functionalized Ionic Liquid-Based Mesoporous Organosilica as a Highly Efficientnanocatalyst for the Knoevenagel Condensation. Catal. Sci. Technol. 2016, 6, 4318–4326.
   Web of Science ®Google Scholar
• Sayed, M.; Shi, Z.; Gholami, F.; Fatehi, P.; Soliman, A.I.A. Ag@TiO2 Nanocomposite as an Efficient Catalyst for Knoevenagel Condensation. ACS Omega 2022, 7, 32393–32400.
   PubMed Web of Science ®Google Scholar
• Jia, X.; Zhang, X.; Wang, Z.; Zhao, S. Tertiary Amine Ionic Liquid Incorporated Fe3O4 Nanoparticles as a Versatile Catalyst for the Knoevenagel Reaction. Synth. Commun. 2022, 52, 774–786.
   Web of Science ®Google Scholar
• Meng, D.; Qiao, Y.; Wang, X.; Wen, W.; Zhao, S. DABCO-Catalyzed Knoevenagel Condensation of Aldehydes with Ethyl Cyanoacetate Using Hydroxy Ionic Liquid as a Promoter. RSC Adv. 2018, 8, 30180–30185.
   PubMed Web of Science ®Google Scholar