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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 39, 2008 - Issue 1
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Original Articles

Tandem Oxidation Process Using Ceric Ammonium Nitrate: Three-Component Synthesis of Trisubstituted Imidazoles Under Aerobic Oxidation Conditions

Ahmad Shaabani Department of Chemistry, Shahid Beheshti University, Tehran, IranCorrespondence[email protected]
,
Ali Maleki Department of Chemistry, Shahid Beheshti University, Tehran, Iran
&
Maryam Behnam Department of Chemistry, Shahid Beheshti University, Tehran, Iran
Pages 102-110 | Received 02 Jun 2008, Published online: 15 Feb 2011

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Kiran D. Dhawale, Ajit P. Ingale, Sandeep V. Shinde, Nitin M. Thorat & Limbraj R. Patil. (2021) ZnO-NPs catalyzed condensation of 2-aminothiophenol and aryl/alkyl nitriles: Efficient green synthesis of 2-substituted benzothiazoles. Synthetic Communications 51:10, pages 1588-1601.
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Neelam P. Prajapati, Rajesh H. Vekariya & Hitesh D. Patel. (2015) Ceric Ammonium Nitrate (CAN)–Catalyzed Multicomponent Reactions: An Efficient Catalyst for Green Organic Synthesis. Synthetic Communications 45:21, pages 2399-2425.
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T. Durai Ananda Kumar, N. Yamini, C.V. S. Subrahmanyam & K. Satyanarayana. (2014) Design and Optimization of Ecofriendly One-Pot Synthesis of 2,4,5-Triaryl-1H-imidazoles by Three-Component Condensation Using Response Surface Methodology. Synthetic Communications 44:15, pages 2256-2268.
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Javad Safari, Shiva Dehghan Khalili & Sayed Hossein Banitaba. (2011) Three-Component, One-Pot Synthesis of 2,4,5-Trisubstituted Imidazoles Catalyzed by TiCl4-SiO2 Under Conventional Heating Conditions or Microwave Irradiation. Synthetic Communications 41:16, pages 2359-2373.
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Minoo Dabiri, Peyman Salehi & Mahboobeh Bahramnejad. (2010) Ecofriendly and Efficient One-Pot Procedure for the Synthesis of Quinazoline Derivatives Catalyzed by an Acidic Ionic Liquid Under Aerobic Oxidation Conditions. Synthetic Communications 40:21, pages 3214-3225.
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Jian-Feng Zhou, Gui-Xia Gong, Xiao-Jun Sun & Yu-Lan Zhu. (2010) Facile Method for One-Step Synthesis of 2,4,5-Triarylimidazoles Under Catalyst-Free, Solvent-Free, and Microwave-Irradiation Conditions. Synthetic Communications 40:8, pages 1134-1141.
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Articles from other publishers (35)

Dnyaneshwar Purushottam Gholap, Ramdas Huse, Sudarshan Dipake & Machhindra K. Lande. (2023) Silica supported lanthanum trifluoroacetate and trichloroacetate as an efficient and reusable water compatible Lewis acid catalyst for synthesis of 2,4,5-triarylimidazoles via a solvent-free green approach . RSC Advances 13:3, pages 2090-2103.
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Vineet Jeena & Nonhlelo Majola. (2023) Acid, Metal and Peroxide-Free Synthesis of 2,4,5-Trisubstituted Imidazoles Commencing from Internal Alkenes Using an Iodine/DMSO System. HETEROCYCLES 106:1, pages 186.
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Hashem Sharghi, Seyyede Faeze Razavi & Mahdi Aberi. (2021) One-Pot Three-Component Synthesis of 2,4,5-Triaryl-1H-imidazoles Using Mn2+ Complex of [7-Hydroxy-4-methyl-8-coumarinyl] Glycine as a Heterogeneous Catalyst. Catalysis Letters 152:6, pages 1769-1783.
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Akansha Agrwal, Soniya Juneja, Smriti Dwivedi & Virendra Kasana. (2022) Molecular docking and antimicrobial analyses of synthesized imidazole derivatives in solvent less condition, adjacent to human pathogenic bacterial strains. Materials Today: Proceedings 57, pages 2250-2254.
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Debopam Sinha, Sudip Biswas, Madhurima Das & Avishek Ghatak. (2021) An eco-friendly, one pot synthesis of tri-substituted imidazoles in aqueous medium catalyzed by RGO supported Au nano-catalyst and computational studies. Journal of Molecular Structure 1242, pages 130823.
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Kesatebrhan Haile Asressu, Chieh-Kai Chan & Cheng-Chung Wang. (2021) TMSOTf-catalyzed synthesis of trisubstituted imidazoles using hexamethyldisilazane as a nitrogen source under neat and microwave irradiation conditions. RSC Advances 11:45, pages 28061-28071.
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Sudarshan S. Dipake, Machhindra K. Lande, Anjali S. Rajbhoj & Suresh T. Gaikwad. (2021) Zeolite ZSM-11 as a reusable and efficient catalyst promoted improved protocol for synthesis of 2,4,5-triarylimidazole derivatives under solvent-free condition. Research on Chemical Intermediates 47:6, pages 2245-2261.
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Hassan Farhid & Ahmad Shaabani. (2020) Magnetic spent coffee ground as an efficient and green catalyst for aerobic oxidation of alcohols and tandem oxidative Groebke–Blackburn–Bienaymé reaction. Journal of the Iranian Chemical Society 18:5, pages 1199-1209.
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Zahra Varzi, Mir Saeed Esmaeili, Reza Taheri-Ledari & Ali Maleki. (2021) Facile synthesis of imidazoles by an efficient and eco-friendly heterogeneous catalytic system constructed of Fe3O4 and Cu2O nanoparticles, and guarana as a natural basis. Inorganic Chemistry Communications 125, pages 108465.
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Bhawna Chopra, Ashwani K. Dhingra & Deo Nandan Prasad. (2021) Imidazole: An Emerging Scaffold Showing its Therapeutic Voyage to Develop Valuable Molecular Entities. Current Drug Research Reviews 12:2, pages 103-117.
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Geetika Patel, Ashok Raj Patel & Subhash Banerjee. (2020) Visible light-emitting diode light-driven one-pot four component synthesis of poly-functionalized imidazoles under catalyst- and solvent-free conditions. New Journal of Chemistry 44:31, pages 13295-13300.
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Foozhan Arpanahi & Bijan Mombeni Goodajdar. (2020) Iron–Phosphonate Nanomaterial: As a Novel and Efficient Organic–Inorganic Hybrid Catalyst for Solvent-Free Synthesis of Tri-Substituted Imidazole Derivatives. Journal of Inorganic and Organometallic Polymers and Materials 30:7, pages 2572-2581.
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Nagaraju Kerru, Lalitha Gummidi, Surya Narayana Maddila, Kranthi Kumar Gangu & Sreekantha B. Jonnalagadda. (2020) Four-component rapid protocol with nickel oxide loaded on fluorapatite as a sustainable catalyst for the synthesis of novel imidazole analogs. Inorganic Chemistry Communications 116, pages 107935.
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C. Sloby. 2019. Catalysis from A to Z. Catalysis from A to Z.
Shivani Naidoo & Vineet Jeena. (2020) Molecular iodine/DMSO mediated oxidation of internal alkynes and primary alcohols using a one-pot, two step approach towards 2,4,5-trisubstituted imidazoles: Substrate scope and mechanistic studies. Tetrahedron 76:12, pages 131028.
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Sumana Y. Kotian, Chakrabhavi Dhananjaya Mohan, Aloir A. Merlo, Shobith Rangappa, S. Chandra Nayak, K.M. Lokanatha Rai & Kanchugarakoppal S. Rangappa. (2020) Small molecule based five-membered heterocycles: A view of liquid crystalline properties beyond the biological applications. Journal of Molecular Liquids 297, pages 111686.
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Ali Maleki, Zahra Varzi & Fereshte Hassanzadeh-Afruzi. (2019) Preparation and characterization of an eco-friendly ZnFe2O4@alginic acid nanocomposite catalyst and its application in the synthesis of 2-amino-3-cyano-4H-pyran derivatives. Polyhedron 171, pages 193-202.
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Zahra Varzi & Ali Maleki. (2019) Design and preparation of ZnS‐ZnFe 2 O 4 : a green and efficient hybrid nanocatalyst for the multicomponent synthesis of 2,4,5‐triaryl‐1 H ‐imidazoles . Applied Organometallic Chemistry 33:8.
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Sundaram Singh & Shivam Bajpai. 2019. Nanocatalysts. Nanocatalysts.
Navjeet Kaur. (2019) Ionic Liquids: A Versatile Medium for the Synthesis of Six-membered Two Nitrogen- Containing Heterocycles. Current Organic Chemistry 23:1, pages 76-96.
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Alexey Yu. Dubovtsev, Dmitry V. Dar'in, Mikhail Krasavin & Vadim Yu. Kukushkin. (2019) Gold‐Catalyzed Oxidation of Internal Alkynes into Benzils and its Application for One‐Pot Synthesis of Five‐, Six‐, and Seven‐Membered Azaheterocycles. European Journal of Organic Chemistry 2019:8, pages 1856-1864.
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Shivani Naidoo & Vineet Jeena. (2018) One‐Pot, Two‐Step Metal and Acid‐Free Synthesis of Trisubstituted Imidazole Derivatives via Oxidation of Internal Alkynes Using an Iodine/DMSO System. European Journal of Organic Chemistry 2019:5, pages 1107-1113.
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Ali Allahresani, Bahare Taheri & M. A. Nasseri. (2018) Fe(III) @g-C3N4 nanocomposite-catalyzed green synthesis of di-indolyloxindole derivatives. Research on Chemical Intermediates 44:11, pages 6741-6751.
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Tahereh Soleymani Ahooie, Najmedin Azizi, Issa Yavari & Mohammad Mahmoudi Hashemi. (2018) Magnetically separable and recyclable g-C3N4 nanocomposite catalyzed one-pot synthesis of substituted imidazoles. Journal of the Iranian Chemical Society 15:4, pages 855-862.
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Majid M. Heravi, Mansoureh Daraie & Vahideh Zadsirjan. (2015) Current advances in the synthesis and biological potencies of tri- and tetra-substituted 1H-imidazoles. Molecular Diversity 19:3, pages 577-623.
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Xiao Guo, Jiaan Shao, Huan Liu, Binhui Chen, Wenteng Chen & Yongping Yu. (2015) Highly efficient and eco-friendly protocol to functionalized imidazoles via ring-opening of α-nitro epoxides. RSC Advances 5:64, pages 51559-51562.
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Vineet Jeena & Ross S. Robinson. (2014) Recent developments in one-pot tandem oxidation process coupling reactions. RSC Adv. 4:77, pages 40720-40739.
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Zohre Zarnegar & Javad Safari. (2014) Catalytic activity of Cu nanoparticles supported on Fe 3 O 4 –polyethylene glycol nanocomposites for the synthesis of substituted imidazoles . New Journal of Chemistry 38:9, pages 4555.
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David I. MaGee, M. Bahramnejad & Minoo Dabiri. (2013) Highly efficient and eco-friendly synthesis of 2-alkyl and 2-aryl-4,5-diphenyl-1H-imidazoles under mild conditions. Tetrahedron Letters 54:21, pages 2591-2594.
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Javad Safari, Shiva Dehghan Khalili, Mehran Rezaei, Sayed Hossein Banitaba & Fereshteh Meshkani. (2010) Nanocrystalline magnesium oxide: a novel and efficient catalyst for facile synthesis of 2,4,5-trisubstituted imidazole derivatives. Monatshefte für Chemie - Chemical Monthly 141:12, pages 1339-1345.
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Vellaisamy Sridharan & J. Carlos Menéndez. (2010) Cerium(IV) Ammonium Nitrate as a Catalyst in Organic Synthesis. Chemical Reviews 110:6, pages 3805-3849.
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Javad Safari, Shiva Dehghan Khalili & Sayed Hossein Banitaba. (2010) A novel and an efficient catalyst for one-pot synthesis of 2,4,5-trisubstituted imidazoles by using microwave irradiation under solvent-free conditions. Journal of Chemical Sciences 122:3, pages 437-441.
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Khodabakhsh Niknam, Mohammad R. Mohammadizadeh, Salimeh Mirzaee & Dariush Saberi. (2010) Silica‐bonded S ‐Sulfonic Acid: A Recyclable Catalyst for the Synthesis of Trisubstituted Imidazoles under Solvent‐free Conditions . Chinese Journal of Chemistry 28:4, pages 663-669.
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Ahmad Shaabani, Ali Maleki & Maryam Behnam. (2009) ChemInform Abstract: Tandem Oxidation Process Using Ceric Ammonium Nitrate: Three‐Component Synthesis of Trisubstituted Imidazoles under Aerobic Oxidation Conditions.. ChemInform 40:25.
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