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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 39, 2009 - Issue 6
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Original Articles

Practical, Ecofriendly, and Chemoselective Method for the Synthesis of 2-Aryl-1-arylmethyl-1H-benzimidazoles Using Amberlite IR-120 as a Reusable Heterogeneous Catalyst in Aqueous Media

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Pages 980-991 | Received 26 May 2008, Published online: 25 Feb 2009

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Madhav J. Hebade, Sambhaji T. Dhumal, Sonali S. Kamble, Tejshri R. Deshmukh, Vijay M. Khedkar, Shrikant V. Hese, Rajesh N. Gacche & Bhaskar S. Dawane. (2023) DTP/SiO2 Assisted Synthesis of New Benzimidazole-Thiazole Conjugates Targeting Antitubercular and Antioxidant Activities. Polycyclic Aromatic Compounds 43:3, pages 2866-2887.
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Soumia Belkharchach, Hana Ighachane, Abdelali Rochdi, Mustapha Ait Ali & Hassan B. Lazrek. (2021) One-pot Synthesis of Benzimidazoles Using H2SO4@HTC as Catalyst. Organic Preparations and Procedures International 53:3, pages 268-277.
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Jia-Hui Hei, Yan-Xiang Zhi, Yuan Zhen, Jun Li & Feng-Xing Zhang. (2013) Syntheses, structures, and luminescence of Co(II), Zn(II), Cd(II) complexes with 1-(2-furylmethylene)-2-(2-furyl)benzimidazole. Journal of Coordination Chemistry 66:8, pages 1320-1329.
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Min Lei, Lei Ma & Lihong Hu. (2012) One-Pot Synthesis of 1H-Benzimidazole Derivatives Using Thiamine Hydrochloride as a Reusable Organocatalyst. Synthetic Communications 42:20, pages 2981-2993.
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Aarti Devi, Shallu, M.L. Sharma & Jasvinder Singh. (2012) Paal–Knorr Pyrrole Synthesis Using Recyclable Amberlite IR 120 Acidic Resin: A Green Approach. Synthetic Communications 42:10, pages 1480-1488.
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Azam Moazeni Bistgani, Abdulhamid Dehghani & Leila Moradi. (2023) Efficient synthesis of 1,2-disubstituted benzimidazoles catalyzed by phosphoric acid as a homogeneous catalyst under mild conditions and investigating their anti-diabetes properties through molecular docking studies and calculations. RSC Advances 13:51, pages 35781-35790.
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Susheel Gulati, Rajvir Singh & Suman Sangwan. (2023) A Review on Green Synthesis and Biological Activities of Medicinally Important Nitrogen and Oxygen Containing Heterocycles. Current Organic Chemistry 26:20, pages 1848-1894.
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Saikat Ranjan Paul, Poushali Saha, Fahad Imtiaz Rahman, Saran Dhar & S. M. Abdur Rahman. (2022) Preferential Synthesis and Pharmacological Evaluation of Mono‐ and Di‐substituted Benzimidazole Derivatives. ChemistrySelect 7:37.
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Priya D. Gavhane, Shuddhodan N. Kadam, Ajay N. Ambhore & Bhaskar S. Dawane. (2021) Silica-supported sodium carbonate: an efficient heterogeneous catalyst for the synthesis of new thiazolopyrimidine derivatives. Research on Chemical Intermediates 47:10, pages 3999-4011.
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L.-H. Zhou, Y.-J. Jin, L.-F. Ma, W.-H. Huang & Y. Wu. (2021) Highly Efficient and Catalyst-Free Synthesis of Benzimidazoles in Aqueous Media. Russian Journal of Organic Chemistry 57:5, pages 825-830.
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C. Kathing, N. G. Singh, J. World Star Rani, R. Nongrum & R. Nongkhlaw. (2020) Facile Synthesis of 1,2-Disubstituted Benzimidazoles Usingp-Toluenesulfonic Acid through Grinding Method. Russian Journal of Organic Chemistry 56:9, pages 1628-1634.
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Kumar Godugu, Venkata Divya Sri Yadala, Mohammad Khaja Mohinuddin Pinjari, Trivikram Reddy Gundala, Lakshmi Reddy Sanapareddy & Chinna Gangi Reddy Nallagondu. (2020) Natural dolomitic limestone-catalyzed synthesis of benzimidazoles, dihydropyrimidinones, and highly substituted pyridines under ultrasound irradiation. Beilstein Journal of Organic Chemistry 16, pages 1881-1900.
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Zafer Ocak. (2020) A Fluorimetric Method Based on an Imidazole Compound for Cu 2+ Determination in Tap Water . Journal of Chemistry 2020, pages 1-7.
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Navneet Kaur, Simranpreet Kaur, Gurpreet Kaur, Aman Bhalla, Sesha Srinivasan & Ganga Ram Chaudhary. (2019) Metallovesicles as smart nanoreactors for green catalytic synthesis of benzimidazole derivatives in water. Journal of Materials Chemistry A 7:29, pages 17306-17314.
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Soumia Belkharchach, Hanane Elayadi, Hana Ighachane, Said Sebti, Mustapha Ait Ali & Hassan B. Lazrek. (2018) p -Toluenesulfonic Acid Coated Natural Phosphate as an Efficient Catalyst for the Synthesis of 2-Substituted Benzimidazole . Journal of Chemical Research 42:12, pages 614-617.
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Linda Toukal, Saida Keraghel, Fatiha Benghanem & Ali Ourari. (2018) Electrochemical, Thermodynamic and Quantum Chemical Studies of Synthesized Benzimidazole Derivative as an Eco-Friendly Corrosion Inhibitor for XC52 Steel in Hydrochloric Acid. International Journal of Electrochemical Science 13:1, pages 951-974.
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Mithun Chakraborty, Barnali Deb, Bapi Dey, Syed Arshad Hussain, Dilip K. Maiti & Swapan Majumdar. (2017) Amberlite IR 120H + Catalyzed N‐C/C‐N Coupled Cylization Strategy to Give Imidazoles: Design and Fabrication of Organic Nanomaterial with AFM Imaging . ChemistrySelect 2:1, pages 241-245.
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Mehdi Forouzani & Hassan Ghasemnejad-Bosra. (2016) Amberlite IR-120 catalyzed, microwave-assisted rapid synthesis of 1-amidoalkyl-2-naphthols. Arabian Journal of Chemistry 9, pages S752-S755.
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Ardeshir Khazaei, Abbas Amini Manesh, Hossein Ahmadian & Hojat Veisi. (2015) Synthesis of 2‐aryl‐1‐arylmethyl‐1H‐1,3‐benzimidazoles catalysed by ferric ammonium sulfate (NH 4 Fe(SO 4 ) 2 ) under solvent‐free conditions . Applied Organometallic Chemistry 30:2, pages 109-111.
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Kiran B. Dhopte, Rahul S. Zambare, Anand V. Patwardhan & Parag R. Nemade. (2016) Role of graphene oxide as a heterogeneous acid catalyst and benign oxidant for synthesis of benzimidazoles and benzothiazoles. RSC Advances 6:10, pages 8164-8172.
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Shivraj Hariram Nile, Brajesh Kumar & Se Won Park. (2015) Chemo selective one-pot synthesis of 2-aryl-1-arylmethyl-1H-benzimidazoles using Amberlite IR-120. Arabian Journal of Chemistry 8:5, pages 685-691.
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Fatemeh Rajabi, Sudipta De & Rafael Luque. (2015) An Efficient and Green Synthesis of Benzimidazole Derivatives Using SBA-15 Supported Cobalt Nanocatalysts. Catalysis Letters 145:8, pages 1566-1570.
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BRAJESH KUMAR, KUMARI SMITA, BRAJENDRA KUMAR & LUIS CUMBAL. (2015) Ultrasound promoted and SiO2/CCl3COOH mediated synthesis of 2-aryl-1-arylmethyl-1H-benzimidazole derivatives in aqueous media: An eco-friendly approach. Journal of Chemical Sciences 126:6, pages 1831-1840.
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Samuthirarajan Senthilkumar & Mayilvasagam Kumarraja. (2014) A facile and highly chemoselective synthesis of 1,2-disubstituted benzimidazoles using hierarchical nanoporous material. Tetrahedron Letters 55:12, pages 1971-1974.
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Amit Pramanik, Rimi Roy, Sagar Khan, Avishek Ghatak & Sanjay Bhar. (2014) Eco-friendly synthesis of 2-aryl-1-arylmethyl-1H-benzimidazoles using alumina-sulfuric acid as a heterogeneous reusable catalyst. Tetrahedron Letters 55:10, pages 1771-1777.
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Ali Maleki, Nakisa Ghamari & Maryam Kamalzare. (2014) Chitosan-supported Fe3O4 nanoparticles: a magnetically recyclable heterogeneous nanocatalyst for the syntheses of multifunctional benzimidazoles and benzodiazepines. RSC Advances 4:19, pages 9416.
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Ramen Jamatia, Mithu Saha & Amarta Kumar Pal. (2014) An efficient facile and one-pot synthesis of benzodiazepines and chemoselective 1,2-disubstituted benzimidazoles using a magnetically retrievable Fe 3 O 4 nanocatalyst under solvent free conditions . RSC Adv. 4:25, pages 12826-12833.
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T. A. Stroganova, V. M. Red’kin, G. A. Kovalenko, V. K. Vasilin & G. D. Krapivin. (2013) Synthesis of 2-Methyl-1-[(5-methylfuran-2-yl)methyl]- and 2-Methyl-1-[(5-methylpyrrol-2-yl)methyl]-1H-benzimidazoles. Chemistry of Heterocyclic Compounds 49:9, pages 1264-1273.
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Shivraj H. Nile, Brajesh Kumar & Se W. Park. (2013) In Vitro Evaluation of Selected Benzimidazole Derivatives as an Antioxidant and Xanthine Oxidase Inhibitors . Chemical Biology & Drug Design 82:3, pages 290-295.
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Dinesh Kumar, Damodara N. Kommi, Rajesh Chebolu, Sanjeev K. Garg, Raj Kumar & Asit K. Chakraborti. (2013) Selectivity control during the solid supported protic acids catalysed synthesis of 1,2-disubstituted benzimidazoles and mechanistic insight to rationalize selectivity. RSC Adv. 3:1, pages 91-98.
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Rajesh Chebolu, Damodara N. Kommi, Dinesh Kumar, Narendra Bollineni & Asit K. Chakraborti. (2012) Hydrogen-Bond-Driven Electrophilic Activation for Selectivity Control: Scope and Limitations of Fluorous Alcohol-Promoted Selective Formation of 1,2-Disubstituted Benzimidazoles and Mechanistic Insight for Rationale of Selectivity. The Journal of Organic Chemistry 77:22, pages 10158-10167.
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Farahnaz K. Behbahani & Parisa Ziaei. (2012) One-pot synthesis of 2-substituted benzimidazoles catalyzed by anhydrous FePO4. Chemistry of Heterocyclic Compounds 48:7, pages 1011-1017.
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Mohamed Afzal Pasha & Aatika Nizam. (2012) Amberlite IR-120 catalyzed, microwave-assisted rapid synthesis of 2-aryl-benzimidazoles. Journal of Saudi Chemical Society 16:3, pages 237-240.
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Sougata Santra, Adinath Majee & Alakananda Hajra. (2012) Nano indium oxide: an efficient catalyst for the synthesis of 1,2-disubstituted benzimidazoles in aqueous media. Tetrahedron Letters 53:15, pages 1974-1977.
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Kaveh Khosravi & Samira Kazemi. (2012) Trans‐3,5‐dihydroperoxy‐3,5‐dimethyl‐1,2‐dioxalane/HBr System as New, Effective, Mild and Non‐toxic Reagent for Synthesis of 2‐Aryl‐1 H ‐benzothiazoles and 2‐Aryl‐1‐arylmethyl‐1 H ‐benzimidazoles . Journal of the Chinese Chemical Society 59:4, pages 557-560.
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F. K. Behbahani & Parisa Ziaei. (2012) A Green Route for the One‐Pot Synthesis of 1,2‐Disubstituted Benzimidazoles Using Iron(III) Phosphate under Solventless Conditions. Chinese Journal of Chemistry 30:1, pages 65-70.
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Hojat Veisi, Alireza Sedrpoushan, Mohammad Ali Zolfigol & Farajollah Mohanazadeh. (2011) Synthesis and application of silica phenyl sulfonic acid as a solid acid heterogeneous catalyst for one‐pot synthesis of 2‐aryl‐1‐arylmethyl‐1H‐1,3‐benzimidazoles and bis(indolyl)methanes in water. Journal of Heterocyclic Chemistry 48:6, pages 1448-1454.
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Hamid Reza Shaterian, Nafiseh Fahimi & Kobra Azizi. (2011) Selective Synthesis of 2‐Aryl‐1‐benzylated‐1 H ‐benzimidazoles . Chinese Journal of Chemistry 29:11, pages 2389-2393.
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Farahnaz K. Behbahani, Parisa Ziaei, Zahra Fakhroueian & Neda Doragi. (2011) An efficient synthesis of 2-arylbenzimidazoles from o-phenylenediamines and arylaldehydes catalyzed by Fe/CeO2–ZrO2 nano fine particles. Monatshefte für Chemie - Chemical Monthly 142:9, pages 901-906.
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L. Srinivasula Reddy, N. C. Gangi Reddy, T. Ram Reddy, Y. Lingappa & Reddy Bodireddy Mohan. (2011) Chemoselective Synthesis of 2-Aryl-1-arylmethyl-1H-benzo[d]imidazoles Using Indion 190 Resin as a Heterogeneous Recyclable Catalyst. Journal of the Korean Chemical Society 55:2, pages 304-307.
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Heiko Leutbecher, Mihaela-Anca Constantin, Sabine Mika, Jürgen Conrad & Uwe Beifuss. (2011) A new laccase-catalyzed domino process and its application to the efficient synthesis of 2-aryl-1H-benzimidazoles. Tetrahedron Letters 52:5, pages 605-608.
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Magdy Ahmed Ibrahim. (2011) Synthetic Utilities of o-Phenylenediamines: Synthetic Approaches for Benzimidazoles, Quinoxalines and Benzo[1,5]diazepines. HETEROCYCLES 83:12, pages 2689.
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Davood Azarifar, Mojgan Pirhayati, Behrooz Maleki, Mehrangiz Sanginabadi & Nejat YamiRaziehRazieh. (2010) Acetic acid-promoted condensation of o-phenylenediamine with aldehydes into 2-aryl-1-(arylmethyl)-1H-benzimidazoles under microwave irradiation. Journal of the Serbian Chemical Society 75:9, pages 1181-1189.
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Kiumars Bahrami, Mohammad M. Khodaei & Akbar Nejati. (2010) Synthesis of 1,2-disubstituted benzimidazoles, 2-substituted benzimidazoles and 2-substituted benzothiazoles in SDS micelles. Green Chemistry 12:7, pages 1237.
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Madhusudana Reddy MUTHUKUR BHOJEGOWD, Aatika NIZAM & Mohamed Afzal PASHA. (2010) Amberlite IR-120: A Reusable Catalyst for N-Formylation of Amines with Formic Acid Using Microwaves. Chinese Journal of Catalysis 31:5, pages 518-520.
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Saikat Das Sharma & Dilip Konwar. (2009) ChemInform Abstract: Practical, Ecofriendly, and Chemoselective Method for the Synthesis of 2‐Aryl‐1‐arylmethyl‐1H‐benzimidazoles Using Amberlite IR‐120 as a Reusable Heterogeneous Catalyst in Aqueous Media.. ChemInform 40:33.
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