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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 36, 2006 - Issue 12
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Original Articles

Zinc Hydroxyapatite–Catalyzed Efficient Synthesis of 5‐Substituted 1H‐Tetrazoles

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Pages 1809-1814 | Received 12 Sep 2005, Published online: 22 Aug 2006

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Venkata Bhavanarushi Pendem, Ramana Tamminana & Madhavi Nannapaneni. (2021) Iron-promoted sulfur sequestration for the substituent-dependent regioselective synthesis of tetrazoles and guanidines. Journal of Sulfur Chemistry 42:5, pages 499-509.
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Gurusamy Ramachandran, Ramachandran Saraswathi, Mayilvasagam Kumarraja, Palsamy Govindaraj & Thirumeni Subramanian. (2018) Efficient synthesis of symmetrical bisamides catalyzed by reusable hydroxyapatite. Synthetic Communications 48:2, pages 216-222.
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Thanaraj Clarina & Velladurai Rama. (2018) [3 + 2] Cycloaddition promoted by zinc oxide nanoparticles anchored on reduced graphene oxide using green solvent. Synthetic Communications 48:2, pages 175-187.
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Abbas Aminimanesh & Safora Shirian. (2017) Synthesis of 5-Substituted Tetrazoles from Nitriles Catalyzed by Sulfamic Acid. Organic Preparations and Procedures International 49:4, pages 346-354.
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G. Venkateshwarlu, K. C. Rajanna & P. K. Saiprakash. (2009) Antimony Trioxide as an Efficient Lewis Acid Catalyst for the Synthesis of 5-Substituted 1H-Tetrazoles. Synthetic Communications 39:3, pages 426-432.
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Articles from other publishers (65)

Mahmoud Nasrollahzadeh, Fahimeh Soleimani, Zahra Nezafat, Yasin Orooji & Fatemeh Ahmadpoor. (2021) Facile synthesis of Cu nanoparticles supported on magnetic lignin-chitosan blend as a highly effective catalyst for the preparation of 5-aryl-1H-tetrazoles. Biomass Conversion and Biorefinery 13:14, pages 12451-12465.
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Ratna Babu Gunturu, Prasanna Babu Racheeti, Srinivasa Rao Pinapati, Anitha Kowthalam, Ramana Tamminana & Rameshraju Rudraraju. (2023) Iron-promoted environmentally benign construction of 2-iodo aroylguanidines and 2-iodo aroyltetrazoles. Journal of Chemical Sciences 135:3.
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Rakhi Vishwakarma, C. P. Vinod, Virendra K. Rathod & Mannepalli Lakshmi Kantam. (2023) Imine Oxidation Catalyzed by Zinc Hydroxyapatite: Kinetic Studies. ChemistrySelect 8:17.
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Rakhi Vishwakarma, Chandrakanth Gadipelly & Lakshmi Kantam Mannepalli. (2022) Advances in Tetrazole Synthesis – An Overview. ChemistrySelect 7:29.
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Leila Kafi-Ahmadi, Shahin Khademinia, Ahmad Poursattar Marjani & Peyman Gozali Balkanloo. (2022) Fabrication of 5-aryl-1H-tetrazoles derivatives by solid-state synthesized MgFe2O4 and MgFe2ZnxO4+δ heterogeneous nanocatalysts. Research on Chemical Intermediates 48:7, pages 2973-2986.
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Sarath C. Sarngadharan, Josh Aronson, Carol Gelbaum, Kris Griffith, Jonathan Faris, Azhar B. Moihdeen, Mikhil Patel, Maryellen Malone, Kent Richman, Charles A. Eckert, Charles L. Liotta & Pamela Pollet. (2022) Synthesis of 5-Substituted Tetrazoles: Reaction of Azide Salts with Organonitriles Catalyzed by Trialkylammonium Salts in Non-polar Media. Organic Process Research & Development 26:5, pages 1432-1441.
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Michel Gruselle, Kaia Tõnsuaadu, Patrick Gredin & Christophe Len. (2022) Apatites based catalysts: A tentative classification. Molecular Catalysis 519, pages 112146.
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Chandrakanth Gadipelly, Gunjan Deshmukh & Lakshmi Kantam Mannepalli. (2021) Transition Metal Exchanged Hydroxyapatite/Fluorapatite Catalysts for C−C and C−N Bond Forming Reactions. The Chemical Record 21:6, pages 1398-1416.
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Maryam Sadat Ghasemzadeh & Batool Akhlaghinia. (2020) An Eco‐Friendly and Efficient Approach for the Synthesis of Tetrazoles via Fe 3 O 4 /HT‐GLYMO‐TA as a New Recoverable Heterogeneous Nanostructured Catalyst . ChemistrySelect 5:21, pages 6440-6452.
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S.N.Murthy Boddapati, Jagan Mohana Rao Saketi, Baby Ramana Mutchu, Hari Babu Bollikolla, Syed Farooq Adil & Mujeeb Khan. (2020) Copper promoted desulfurization and C-N cross coupling reactions: Simple approach to the synthesis of substituted 2-aminobenzoxazoles and 2,5-disubstituted tetrazole amines. Arabian Journal of Chemistry 13:2, pages 4477-4494.
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Mahmoud Abd El Aleem Ali Ali El‐Remaily & O.M. Elhady. (2019) Iron (III)‐porphyrin Complex FeTSPP as an efficient catalyst for synthesis of tetrazole derivatives via [2 + 3]cycloaddition reaction in aqueous medium . Applied Organometallic Chemistry 33:8.
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Teddy Tite, Adrian-Claudiu Popa, Liliana Balescu, Iuliana Bogdan, Iuliana Pasuk, José Ferreira & George Stan. (2018) Cationic Substitutions in Hydroxyapatite: Current Status of the Derived Biofunctional Effects and Their In Vitro Interrogation Methods. Materials 11:11, pages 2081.
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Samaresh Layek, Rakesh Ganguly & Devendra D. Pathak. (2018) Unprecedented formation of a μ -oxobridged polymeric copper(II) complex: Evaluation of catalytic activity in synthesis of 5-substituted 1 H -tetrazoles. Journal of Organometallic Chemistry 870, pages 16-22.
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Hesam Tourani, M. Reza Naimi‐Jamal & Mohammad G. Dekamin. (2018) Preparation of 5‐Substituted‐1H‐Tetrazoles Catalyzed by MOFs via Two Strategies: Direct Condensation of Aryl Nitriles with Sodium Azide, and Tri‐Component Reaction Method. ChemistrySelect 3:28, pages 8332-8337.
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S.N. Murthy Boddapati, A. Emmanuel Kola, Surendra Babu Kesana & Hari Babu Bollikolla. (2018) Temperature dependent regioselective synthesis of aryl tetrazole amines using copper source. Journal of Organometallic Chemistry 866, pages 177-183.
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Kondraganti Lakshmi, Manabolu Surendra Babu & Dittakavi Ramachandran. (2018) Cobalt-promoted regioselective preparation of aryl tetrazole amines. Journal of Chemical Sciences 130:5.
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Alireza Najafi Chermahini, Nikzad Andisheh & Abbas Teimouri. (2018) KIT-6-anchored sulfonic acid groups as a heterogeneous solid acid catalyst for the synthesis of aryl tetrazoles. Journal of the Iranian Chemical Society 15:4, pages 831-838.
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Jamshid Azarnia Mehraban, Kobra Azizi, Mahsa Sadat Jalali & Akbar Heydari. (2018) Choline Azide: New Reagent and Ionic Liquid in Catalyst‐Free and Solvent‐Free Synthesis of 5‐Substituted‐1 H ‐Tetrazoles: A Triple Function Reagent . ChemistrySelect 3:1, pages 116-121.
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Fooleswar Verma, Anjumala Sahu, Puneet K. Singh, Ankita Rai, Manorama Singh & Vijai K. Rai. (2018) Visible-light driven regioselective synthesis of 1 H -tetrazoles from aldehydes through isocyanide-based [3 + 2] cycloaddition . Green Chemistry 20:16, pages 3783-3789.
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B. Yakambram, A. Jaya Shree, L. Srinivasula Reddy, T. Satyanarayana, P. Naveen & Rakeshwar Bandichhor. (2018) Urea mediated 5-substituted-1H-tetrazole via [3 + 2] cycloaddition of nitriles and sodium azide. Tetrahedron Letters 59:5, pages 445-449.
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Baji vali Shaik, Mohan Seelam, Ramana Tamminana & Prasad Rao Kammela. (2017) Efficient Copper‐Promoted Tandem Multi‐Component Strategy: The Synthesis of 1‐ Aryl/Alkyl‐5‐( N ‐Benzoylamino) Tetrazoles and Guanidine's . ChemistrySelect 2:35, pages 11521-11525.
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R.D. Padmaja, Sourav Rej & Kaushik Chanda. (2017) Environmentally friendly, microwave-assisted synthesis of 5-substituted 1 H-tetrazoles by recyclable CuO nanoparticles via (3+2) cycloaddition of nitriles and NaN3. Chinese Journal of Catalysis 38:11, pages 1918-1924.
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Deelip S. Rekunge, Krishna S. Indalkar & Ganesh U. Chaturbhuj. (2016) Activated Fuller’s earth as an inexpensive, eco-friendly, efficient catalyst for the synthesis of 5-aryl 1-H-tetrazole via [3+2] cycloaddition of nitriles and sodium azide. Tetrahedron Letters 57:51, pages 5815-5819.
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Narsimha Reddy Penthala, Shobanbabu Bommagani, Jaishankar Yadlapalli & Peter A. Crooks. (2016) A novel and efficient tributyltin azide-mediated synthesis of 1H-tetrazolylstilbenes from cyanostilbenes. Tetrahedron Letters 57:16, pages 1807-1810.
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Soheila Khaghaninejad, Majid M. Heravi, Tayebeh Hosseinnejad, Hossein A. Oskooie & Mehdi Bakavoli. (2015) Regio-selective synthesis of 5-substituted 1H-tetrazoles using ionic liquid [BMIM]N3 in solvent-free conditions: a click reaction. Research on Chemical Intermediates 42:3, pages 1593-1610.
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Javad Safaei-Ghomi, Soleiman Paymard-Samani, Safura Zahedi & Hossein Shahbazi-Alavi. (2015) Sonochemical synthesis of 5-substituted 1 H -tetrazoles catalyzed by ZrP 2 O 7 nanoparticles and regioselective conversion into new 2,5-disubstituted tetrazoles . Zeitschrift für Naturforschung B 70:11, pages 819-828.
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Fatemeh Abrishami, Maryam Ebrahimikia & Fatemeh Rafiee. (2015) Synthesis of 5‐substituted 1 H ‐tetrazoles using a recyclable heterogeneous nanonickel ferrite catalyst . Applied Organometallic Chemistry 29:11, pages 730-735.
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Wolf Peter Fehlhammer & Wolfgang Beck. (2015) Azide Chemistry – An Inorganic Perspective, Part II [‡] [3+2]‐Cycloaddition Reactions of Metal Azides and Related Systems . Zeitschrift für anorganische und allgemeine Chemie 641:10, pages 1599-1678.
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Sara S. E. Ghodsinia & Batool Akhlaghinia. (2015) A rapid metal free synthesis of 5-substituted-1H-tetrazoles using cuttlebone as a natural high effective and low cost heterogeneous catalyst. RSC Advances 5:62, pages 49849-49860.
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Alireza Najafi Chermahini, Masoud Khani Omran, Hossein A. Dabbagh, Gholamhossein Mohammadnezhad & Abbas Teimouri. (2015) Application of a functionalized mesoporous silica catalyst to the synthesis of tetrazoles. New Journal of Chemistry 39:6, pages 4814-4820.
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Nasrin Razavi & Batool Akhlaghinia. (2015) Cu( ii ) immobilized on aminated epichlorohydrin activated silica (CAES): as a new, green and efficient nanocatalyst for preparation of 5-substituted-1H-tetrazoles . RSC Advances 5:16, pages 12372-12381.
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Santosh Kumar Prajapti, Atulya Nagarsenkar & Bathini Nagendra Babu. (2014) An efficient synthesis of 5-substituted 1H-tetrazoles via B(C6F5)3 catalyzed [3+2] cycloaddition of nitriles and sodium azide. Tetrahedron Letters 55:24, pages 3507-3510.
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Pavnesh Mani, Ashawani Kumar Singh & Satish Kumar Awasthi. (2014) AgNO3 catalyzed synthesis of 5-substituted-1H-tetrazole via [3+2] cycloaddition of nitriles and sodium azide. Tetrahedron Letters 55:11, pages 1879-1882.
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Dan Kong, Yanyan Liu, Juan Zhang, Hongbian Li, Xiangyu Wang, Guangyu Liu, Baojun Li & Zheng Xu. (2014) Hierarchically porous AlPO-5-based microspheres as heterogeneous catalysts for the synthesis of 5-substituted 1H-tetrazoles via [3+2] cycloaddition. New J. Chem. 38:7, pages 3078-3083.
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Farzaneh Dehghani, Ali Reza Sardarian & Mohsen Esmaeilpour. (2013) Salen complex of Cu(II) supported on superparamagnetic Fe3O4@SiO2 nanoparticles: An efficient and recyclable catalyst for synthesis of 1- and 5-substituted 1H-tetrazoles. Journal of Organometallic Chemistry 743, pages 87-96.
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Nilo Zanatta, Fabio M. da Silva, Andreia M. P. W. da Silva, Estefania da C. Aquino, Helio G. Bonacorso & Marcos A. P. Martins. (2013) An Efficient Two-Step Synthesis of New 5-Substituted-1 H -tetrazoles of Biological Interest . Journal of Heterocyclic Chemistry 50:4, pages 868-873.
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Anton V. Gulevich, Alexander S. Dudnik, Natalia Chernyak & Vladimir Gevorgyan. (2013) Transition Metal-Mediated Synthesis of Monocyclic Aromatic Heterocycles. Chemical Reviews 113:5, pages 3084-3213.
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Ali Khalafi-Nezhad & Somayeh Mohammadi. (2013) Highly efficient synthesis of 1- and 5-substituted 1H-tetrazoles using chitosan derived magnetic ionic liquid as a recyclable biopolymer-supported catalyst. RSC Advances 3:13, pages 4362.
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Dipak R. Patil, Yogesh B. Wagh, Pravin G. Ingole, Kripal Singh & Dipak S. Dalal. (2013) β-Cyclodextrin-mediated highly efficient [2+3] cycloaddition reactions for the synthesis of 5-substituted 1H-tetrazoles. New Journal of Chemistry 37:10, pages 3261.
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David Cantillo, Bernhard Gutmann & C. Oliver Kappe. (2012) An Experimental and Computational Assessment of Acid-Catalyzed Azide-Nitrile Cycloadditions. The Journal of Organic Chemistry 77:23, pages 10882-10890.
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Dipak R. Patil, Mukesh B. Deshmukh & Dipak S. Dalal. (2012) Ammonium acetate mediated synthesis of 5-substituted 1H-tetrazoles. Journal of the Iranian Chemical Society 9:5, pages 799-803.
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Jessica L. Durham, Joan N. Tirado, Stanley A. Knott, Meghan K. Oh, Robert McDonald & Lisa F. Szczepura. (2012) Preparation of a Family of Hexanuclear Rhenium Cluster Complexes Containing 5-(Phenyl)tetrazol-2-yl Ligands and Alkylation of 5-Substituted Tetrazolate Ligands. Inorganic Chemistry 51:14, pages 7825-7836.
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