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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 35, 2005 - Issue 8
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Original Articles

Fe3+‐Montmorillonite as Effective, Recyclable Catalyst for Paal–Knorr Pyrrole Synthesis Under Mild Conditions

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Pages 1051-1057 | Received 20 Oct 2004, Published online: 16 Aug 2006

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Avula Balakrishna, António Aguiar, Pedro J. M. Sobral, Mohmmad Younus Wani, Joana Almeida e Silva & Abilio J. F. N. Sobral. (2019) Paal–Knorr synthesis of pyrroles: from conventional to green synthesis. Catalysis Reviews 61:1, pages 84-110.
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Dilek Akbaşlar, Onur Demirkol & Sultan Giray. (2014) Paal–Knorr Pyrrole Synthesis in Water. Synthetic Communications 44:9, pages 1323-1332.
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Katla Ramesh, Sabbavarapu Narayana Murthy & Yadavalli Venkata Durga Nageswar. (2012) Synthesis of N-Substituted Pyrroles Under Catalyst- and Solvent-Free Conditions. Synthetic Communications 42:16, pages 2471-2477.
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Sujaya Dasgupta & Béla Török. (2008) APPLICATION OF CLAY CATALYSTS IN ORGANIC SYNTHESIS. A REVIEW. Organic Preparations and Procedures International 40:1, pages 1-65.
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Erika Moreno-Suárez, Rafael Avila-Acosta, Karen Sánchez-Ramírez, Juan-Carlos Castillo & Mario A. Macías. (2023) Crystallographic, spectroscopic and thermal studies of 1-(4-bromophenyl)-5-(2,5-dimethyl-1 H -pyrrol-1-yl)-3-methyl-1 H -pyrazole . Acta Crystallographica Section C Structural Chemistry 79:11, pages 472-479.
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Tao Shi, Gaofeng Yin, Xiaodong Wang, Yongxia Xiong, Yan Peng, Shuang Li, Yaofu Zeng & Zhen Wang. (2023) Recent advances in the syntheses of pyrroles. Green Synthesis and Catalysis 4:1, pages 20-34.
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Y B. N. Tran & Phuong T. K. Nguyen. (2022) A New Zinc‐Based Metal‐Organic Framework for Catalytic Synthesis of N ‐Substituted Pyrroles . ChemistrySelect 7:16.
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Robert H.E. Schirmacher, Daniel Rösch & Franziska Thomas. (2021) Hexafluoroisopropanol as solvent and promotor in the Paal-Knorr synthesis of N-substituted diaryl pyrroles. Tetrahedron 83, pages 131985.
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Yunzhu Wang, Shinya Furukawa, Xinpu Fu & Ning Yan. (2019) Organonitrogen Chemicals from Oxygen-Containing Feedstock over Heterogeneous Catalysts. ACS Catalysis 10:1, pages 311-335.
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Liudvikas Akelis, Jolanta Rousseau, Robertas Juskenas, Jelena Dodonova, Cyril Rousseau, Stéphane Menuel, Dominique Prevost, Sigitas Tumkevičius, Eric Monflier & Frédéric Hapiot. (2016) Greener Paal-Knorr Pyrrole Synthesis by Mechanical Activation. European Journal of Organic Chemistry 2016:1, pages 31-35.
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Sheenu Abbat, Devendra Dhaked, Minhajul Arfeen & Prasad V. Bharatam. (2015) Mechanism of the Paal–Knorr reaction: the importance of water mediated hemialcohol pathway. RSC Advances 5:107, pages 88353-88366.
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Hyejin Cho, Richard Madden, Bilal Nisanci & Béla Török. (2015) The Paal–Knorr reaction revisited. A catalyst and solvent-free synthesis of underivatized and N-substituted pyrroles. Green Chemistry 17:2, pages 1088-1099.
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Belenahalli M. Vinoda & Jayappa Manjanna. (2014) Dissolution of iron in salicylic acid and cation exchange between Fe(II)-salicylate and Na-montmorillonite to form Fe(II)-montmorillonite. Applied Clay Science 97-98, pages 78-83.
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Stéphane Menuel, Jolanta Rousseau, Cyril Rousseau, Edita Vaičiūnaite, Jelena Dodonova, Sigitas Tumkevičius & Eric Monflier. (2014) Access to Pyrrole Derivatives in Water with the Assistance of Methylated Cyclodextrins. European Journal of Organic Chemistry 2014:20, pages 4356-4361.
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Chun J. Shi, Yan F. Tai & Hong T. Liu. (2013) Improved Regioselective Mononitration of o-Xylene over HBEA-500 Zeolite Catalyst. Bulletin of the Korean Chemical Society 34:11, pages 3485-3487.
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Najmadin Azizi, Anahita Davoudpour, Farshid Eskandari & Ehlham Batebi. (2012) Squaric acid catalyzed simple synthesis of N-substituted pyrroles in green reaction media. Monatshefte für Chemie - Chemical Monthly 144:3, pages 405-409.
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Jaideep B. Bharate, Rajni Sharma, Subrayashastry Aravinda, Vivek K. Gupta, Baldev Singh, Sandip B. Bharate & Ram A. Vishwakarma. (2013) Montmorillonite clay catalyzed synthesis of functionalized pyrroles through domino four-component coupling of amines, aldehydes, 1,3-dicarbonyl compounds and nitroalkanes. RSC Advances 3:44, pages 21736.
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R.W. Mccabe & J.M. Adams. 2013. Handbook of Clay Science. Handbook of Clay Science 491 538 .
Hossein Reza Darabi, Kioumars Aghapoor, Abbas Darestani Farahani & Farshid Mohsenzadeh. (2012) Vitamin B1 as a metal-free organocatalyst for greener Paal–Knorr pyrrole synthesis. Environmental Chemistry Letters 10:4, pages 369-375.
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Ali Rahmatpour. (2012) Polystyrene-supported GaCl3 as a highly efficient and recyclable heterogeneous Lewis acid catalyst for one-pot synthesis of N-substituted pyrroles. Journal of Organometallic Chemistry 712, pages 15-19.
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Kioumars Aghapoor, Leila Ebadi-Nia, Farshid Mohsenzadeh, Mina Mohebi Morad, Yadollah Balavar & Hossein Reza Darabi. (2012) Silica-supported bismuth(III) chloride as a new recyclable heterogeneous catalyst for the Paal–Knorr pyrrole synthesis. Journal of Organometallic Chemistry 708-709, pages 25-30.
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V.S.V. Satyanarayana & A. Sivakumar. (2011) Ultrasound-assisted synthesis of 2,5-dimethyl-N-substituted pyrroles catalyzed by uranyl nitrate hexahydrate. Ultrasonics Sonochemistry 18:5, pages 917-922.
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Ali Rahmatpour. (2011) Cellulose sulfuric acid as a biodegradable and recoverable solid acid catalyst for one pot synthesis of substituted pyrroles under solvent-free conditions at room temperature. Reactive and Functional Polymers 71:1, pages 80-83.
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Ali Rahmatpour & Jamal Aalaie. (2010) One‐pot synthesis of N‐substituted pyrroles catalyzed by polystyrene‐supported aluminum chloride as a reusable heterogeneous lewis acid catalyst. Heteroatom Chemistry 22:1, pages 85-90.
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Zerong Wang. 2010. Comprehensive Organic Name Reactions and Reagents. Comprehensive Organic Name Reactions and Reagents 2107 2110 .
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Ying Cheng, Jiang-Hua Peng & Jia-Qi Li. (2010) Orthogonal Synthesis of Densely Functionalized Pyrroles and Thiophenes from the Reactions of Imidazo[1,5- a ]pyridine Carbene-Derived Zwitterions with Electron-Deficient Alkynes . The Journal of Organic Chemistry 75:7, pages 2382-2388.
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Shizhen Yuan, Zhen Li & Ling Xu. (2010) A simple synthesis of pyrroles catalyzed by acidic resin under solvent‐free condition. Journal of Heterocyclic Chemistry 47:2, pages 446-448.
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G. Karthikeyan & A. Pandurangan. (2009) Heteropolyacid (H3PW12O40) supported MCM-41: An efficient solid acid catalyst for the green synthesis of xanthenedione derivatives. Journal of Molecular Catalysis A: Chemical 311:1-2, pages 36-45.
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Haitang Luo, Yuru Kang, Hongyun Nie & Liming Yang. (2013) Fe 3+ ‐Montmorillonite: An Efficient Solid Catalyst for One‐Pot Synthesis of Decahydroacridine Derivatives . Journal of the Chinese Chemical Society 55:6, pages 1280-1285.
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Zhan-Hui Zhang, Jian-Jiong Li & Tong-Shan Li. (2008) Ultrasound-assisted synthesis of pyrroles catalyzed by zirconium chloride under solvent-free conditions. Ultrasonics Sonochemistry 15:5, pages 673-676.
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Haitang Luo, Yuru Kang, Qi Li & Liming Yang. (2008) Sulfamic acid as efficient and reusable catalytic system for the synthesis of pyrrole, furan, and thiophene derivatives. Heteroatom Chemistry 19:2, pages 144-148.
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Jiuxi Chen, Huayue Wu, Zhiguo Zheng, Can Jin, Xingxian Zhang & Weike Su. (2006) An approach to the Paal–Knorr pyrroles synthesis catalyzed by Sc(OTf)3 under solvent-free conditions. Tetrahedron Letters 47:30, pages 5383-5387.
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Guoyong Song, Bo Wang, Guang Wang, Yuru Kang, Tao Yang & Liming Yang. (2005) Fe 3+ ‐Montmorillonite as Effective, Recyclable Catalyst for Paal—Knorr Pyrrole Synthesis under Mild Conditions. . ChemInform 36:36.
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