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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 34, 2004 - Issue 20
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Original Articles

Organic Reactions in Ionic Liquids: Gewald Synthesis of 2‐Aminothiophenes Catalyzed by Ethylenediammonium Diacetate

Yi Hu Ningbo Institute of Technology, Zhejiang University, Ningbo, 315104, P.R. China; Department of Chemistry, Zhejiang University (Xi Xi Campus), Hangzhou, 310028, P.R. China
,
Zhen‐Chu Chen Ningbo Institute of Technology, Zhejiang University, Ningbo, 315104, P.R. China; Department of Chemistry, Zhejiang University (Xi Xi Campus), Hangzhou, 310028, P.R. ChinaCorrespondence[email protected]
,
Zhang‐Gao Le Department of Chemistry, Zhejiang University (Xi Xi Campus), Hangzhou, 310028, P.R. China
&
Qin‐Guo Zheng Pharmaceutical Science Research Institute, Aston University, Aston Triangle, Birmingham, B4 7ET, UK
Pages 3801-3806 | Received 10 May 2004, Published online: 19 Apr 2010

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Navjeet Kaur. (2019) Ionic liquid assisted synthesis of S-heterocycles. Phosphorus, Sulfur, and Silicon and the Related Elements 194:3, pages 165-185.
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Venkata Rao Kaki, Raghuram Rao Akkinepalli, Pran Kishore Deb & Mallikarjuna Rao Pichika. (2015) Basic Ionic Liquid [bmIm]OH–Mediated Gewald Reaction as Green Protocol for the Synthesis of 2-Aminothiophenes. Synthetic Communications 45:1, pages 119-126.
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Ahmed El-Mekabaty. (2014) Chemistry of 2-Amino-3-carbethoxythiophene and Related Compounds. Synthetic Communications 44:1, pages 1-31.
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Esmail Rezaei-Seresht, Reza Tayebee & Mohammad Yasemi. (2013) KG-60-Piperazine as a New Heterogeneous Catalyst for Gewald Three-Component Reaction. Synthetic Communications 43:13, pages 1859-1864.
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Hassan Sheibani & Maryam Babaie. (2009) Three-Component Reaction to Form 1,4-Dihydropyrano[2,3-c]pyrazol-5-yl Cyanides. Synthetic Communications 40:2, pages 257-265.
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M. Syamala. (2009) Recent Progress in Three-Component Reactions. An Update. Organic Preparations and Procedures International 41:1, pages 1-68.
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Wolf-Diethard Pfeiffer, Horst Dollinger & Peter Langer. (2009) Synthesis of 5-Thioxo-hexahydrobenzo[b]thiopheno[2,3-d]-1,2,4-triazolo[1,5-c]pyrimidines and Related Compounds Based on Cyclocondensations of 2-Isothiocyanato-3-cyano-4,5,6,7-tetrahydrobenzo[b]thiophene. Phosphorus, Sulfur, and Silicon and the Related Elements 184:3, pages 626-637.
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Yi Hu, Ping Wei, He Huang, Shi‐Qing Han & Ping‐Kai Ouyang. (2006) Synthesis of 2‐Aminothiophenes on Ionic Liquid Phase Support using the Gewald Reaction. Synthetic Communications 36:11, pages 1543-1548.
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Articles from other publishers (32)

Aslıhan Ayvaz, Sinem Gorkem Demirbaş, Ahmet Demirbaş & Neslihan Demirbaş. (2023) One-Pot Multicomponent Reactions in Deep Eutectic Solvents. Current Organic Chemistry 27:7, pages 585-620.
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Mohamed E. Khalifa. (2020) Synthesis and molecular modeling of novel bio-functional moieties derived from 2-cyanoacetamide-3,4,5-substituted thiophene as human carcinoma growth inhibitors. Journal of Molecular Structure 1215, pages 128270.
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C. Sloby. 2019. Catalysis from A to Z. Catalysis from A to Z.
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Mohamed A. El‐Borai, Hala F. Rizk, Seham A. Ibrahim & Amira K. Fares. (2019) An Eco‐friendly Synthesis and Biological Screening of Fused Heterocyclic Compounds Containing a Thiophene Moiety via Gewald Reaction . Journal of Heterocyclic Chemistry 56:10, pages 2787-2795.
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Navjeet Kaur. (2019) Metal and Non-Metal Catalysts in the Synthesis of Five-Membered S-Heterocycles. Current Organic Synthesis 16:2, pages 258-275.
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Prabakaran Kumaresan, Zeller Matthias & Rajendra Prasad Karnam Jayarampillai. (2016) Efficient Synthesis of Functionalized Thienocarbazoles Catalyzed by l ‐proline . Journal of Heterocyclic Chemistry 54:3, pages 1891-1897.
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Ahmad Shaabani, Seyyed Emad Hooshmand & Hadi Afaridoun. (2016) A green chemical approach: a straightforward one-pot synthesis of 2-aminothiophene derivatives via Gewald reaction in deep eutectic solvents. Monatshefte für Chemie - Chemical Monthly 148:4, pages 711-716.
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Pengyu Li, Jianguo Du, Yujia Xie, Minli Tao & Wen-Qin Zhang. (2016) Highly Efficient Polyacrylonitrile Fiber Catalysts Functionalized by Aminopyridines for the Synthesis of 3-Substituted 2-Aminothiophenes in Water. ACS Sustainable Chemistry & Engineering 4:3, pages 1139-1147.
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Ram W. Sabnis. (2016) The Gewald reaction in dye chemistry. Coloration Technology 132:1, pages 49-82.
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Fang Xu, Yujin Li, Fengshuang Xu, Qing Ye, Liang Han, Jianrong Gao & Wubin Yu. (2014) Solvent-Free synthesis of 2-Aminothiophene-3-Carbonitrile Derivatives Using High-Speed Vibration Milling. Journal of Chemical Research 38:7, pages 450-452.
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William Shearouse, Maxwell Shumba & James Mack. (2014) A Solvent-Free, One-Step, One-Pot Gewald Reaction for Alkyl-aryl Ketones via Mechanochemistry. Applied Sciences 4:2, pages 171-179.
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G. Thirupathi, M. Venkatanarayana, P. K. Dubey & Y. Bharathi Kumari. (2013) Eco-friendly synthesis and antimicrobial activities of substituted-5-(1H-indol-3-yl)methylene)-2,2-dimethyl-1,3-dioxane-4,6-dione derivatives. Medicinal Chemistry Research 23:3, pages 1569-1580.
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Binhui Chen, Hangcheng Ni, Xiao Guo, Guolin Zhang & Yongping Yu. (2014) Facile preparation of 3,5-disubstituted-4-aminothiophene-2-carbaldehyde from a novel unexpected domino reaction of vinyl azides and 1,4-dithiane-2,5-diol. RSC Adv. 4:84, pages 44462-44465.
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G. Thirupathi, M. Venkatanarayana, P. K. Dubey & Y. Bharathi Kumari. (2012) L-Tyrosine as an Eco-Friendly and Efficient Catalyst for Knoevenagel Condensation of Arylaldehydes with Meldrum’s Acid in Solvent-Free Condition under Grindstone Method. Organic Chemistry International 2012, pages 1-4.
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Reza Tayebee, S. Javad Ahmadi, Esmaeil Rezaei Seresht, Farzad Javadi, Mohammad A. Yasemi, Morteza Hosseinpour & Behrouz Maleki. (2012) Commercial Zinc Oxide: A Facile, Efficient, and Eco-friendly Catalyst for the One-Pot Three-Component Synthesis of Multisubstituted 2-Aminothiophenes via the Gewald Reaction. Industrial & Engineering Chemistry Research 51:44, pages 14577-14582.
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Yuliang Zhang & Zhongqiang Zhou. (2012) A Solvent-Free Protocol for the Green Synthesis of 5-Arylidene-2,4-thiazolidinediones Using Ethylenediamine Diacetate as Catalyst. Organic Chemistry International 2012, pages 1-5.
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Martín J. Riveira & Mirta P. Mischne. (2012) One‐Pot Organocatalytic Tandem Aldol/Polycyclization Reactions between 1,3‐Dicarbonyl Compounds and α,β,γ,δ‐Unsaturated Aldehydes for the Straightforward Assembly of Cyclopenta[ b ]furan‐Type Derivatives: New Insight into the Knoevenagel Reaction . Chemistry – A European Journal 18:8, pages 2382-2388.
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Xian-Gui Huang, Jia Liu, Jiangmeng Ren, Tao Wang, Weidong Chen & Bu-Bing Zeng. (2011) A facile and practical one-pot synthesis of multisubstituted 2-aminothiophenes via imidazole-catalyzed Gewald reaction. Tetrahedron 67:34, pages 6202-6205.
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Farid Moeinpour, Raheleh Omidinia, Nadieh Dorostkar-Ahmadi & Bentalhoda Khoshdeli. (2011) Cesium Carbonate as a Heterogeneous Base Catalyst for Synthesis of 2-Aminothiophenes via Gewald Reaction. Bulletin of the Korean Chemical Society 32:6, pages 2091-2092.
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Zerong Wang. 2010. Comprehensive Organic Name Reactions and Reagents. Comprehensive Organic Name Reactions and Reagents 1213 1216 .
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Natasha R. Singh, Dyer Narinesingh & Gurdial Singh. (2010) Immobilization of β-galactosidase onto Sepharose and stabilization in room temperature ionic liquids. Journal of Molecular Liquids 152:1-3, pages 19-27.
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Marta Feroci, Isabella Chiarotto, Leucio Rossi & Achille Inesi. (2008) Activation of Elemental Sulfur by Electrogenerated Cyanomethyl Anion: Synthesis of Substituted 2‐Aminothiophenes by the Gewald Reaction. Advanced Synthesis & Catalysis 350:17, pages 2740-2746.
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Ramadan Ahmed Mekheimer, Mohamed Abdallah Ameen & Kamal Usef Sadek. (2008) Solar thermochemical reactions II1: Synthesis of 2-aminothiophenes via Gewald reaction induced by solar thermal energy. Chinese Chemical Letters 19:7, pages 788-790.
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Vasile I. Pârvulescu & Christopher Hardacre. (2007) Catalysis in Ionic Liquids. Chemical Reviews 107:6, pages 2615-2665.
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Yi Hu, Ping Wei, He Huang, Shi-Qing Han & Ping-Kai Ouyang. (2006) Microwave-assisted Gewald Synthesis of 2-Aminothiophenes Using Functional Ionic Liquid as Soluble Support. HETEROCYCLES 68:2, pages 375.
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Gianluca Bianchini, Marcello Crucianelli, Francesco De Angelis, Veronica Neri & Raffaele Saladino. (2005) Highly efficient C–H insertion reactions of hydrogen peroxide catalyzed by homogeneous and heterogeneous methyltrioxorhenium systems in ionic liquids. Tetrahedron Letters 46:14, pages 2427-2432.
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Yi Hu, Zhen‐Chu Chen, Zhang‐Gao Le & Qin‐Guo Zheng. (2005) Organic Reactions in Ionic Liquids: Gewald Synthesis of 2‐Aminothiophenes Catalyzed by Ethylenediammonium Diacetate.. ChemInform 36:12.
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