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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 40, 2009 - Issue 1
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Original Articles

Fast, Solvent-Free, Microwave-Promoted Friedländer Annulation with a Reusable Solid Catalyst

Davide Garella Dipartimento di Scienza e Tecnologia del Farmaco, Università di Torino, Torino, Italy
,
Alessandro Barge Dipartimento di Scienza e Tecnologia del Farmaco, Università di Torino, Torino, Italy
,
Dharita Upadhyaya Dipartimento di Scienza e Tecnologia del Farmaco, Università di Torino, Torino, Italy
,
Zalua Rodríguez Dipartimento di Scienza e Tecnologia del Farmaco, Università di Torino, Torino, Italy; Centro de Química Farmacéutica, Ciudad de La Habana, Cuba
,
Giovanni Palmisano Dipartimento di Scienze Chimiche e Ambientali, Università dell'Insubria, Como, Italy
&
Giancarlo Cravotto Dipartimento di Scienza e Tecnologia del Farmaco, Università di Torino, Torino, ItalyCorrespondence[email protected]
Pages 120-128 | Received 20 Dec 2008, Published online: 09 Dec 2009

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Ashish Patel, Stuti Patel, Meshwa Mehta, Yug Patel, Rushi Patel, Drashti Shah, Darshini Patel, Umang Shah, Mehul Patel, Swayamprakash Patel, Nilay Solanki, Tushar Bambharoliya, Sandip Patel, Afzal Nagani, Harnisha Patel, Jitendra Vaghasiya, Hirak Shah, Bijal Prajapati, Mrudangsinh Rathod, Bhargav Bhimani, Riddhisiddhi Patel, Vashisth Bhavsar, Brijesh Rakholiya, Maitri Patel & Prexa Patel. (2022) A review on synthetic investigation for quinoline- recent green approaches. Green Chemistry Letters and Reviews 15:2, pages 337-372.
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Nader Ghaffari Khaligh, Taraneh Mihankhah & Mohd Rafie Johan. (2020) Synthesis of Quinoline Derivatives via the Friedländer Annulation Using a Sulfonic Acid Functionalized Liquid Acid as Dual Solvent-Catalyst. Polycyclic Aromatic Compounds 40:4, pages 1223-1237.
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Anil S. Mali, Abhishek B. Sharma & Ganesh U. Chaturbhuj. (2020) Sulfated Polyborate Catalyzed Selective Friedlander Annulation for Synthesis of Highly Functionalized Quinolines. Organic Preparations and Procedures International 52:4, pages 297-303.
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Mahmoud Nassiri. (2013) Simple, One-Pot, and Three-Component Coupling Reactions of Azaarenes (Phenanthridine, Isoquinoline, and Quinoline), with Acetylenic Esters Involving Methyl Propiolate or Ethyl Propiolate in the Presence of NH-Heterocyclic or 1,3-Dicarbonyl Compounds. Synthetic Communications 43:2, pages 157-168.
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Articles from other publishers (32)

Bandarupalli Krishna & Sounak Roy. (2023) Efficient Synthesis of Quinolines from 2‐Aminoaryl Ketones with α‐Methylene Carbonyl Derivatives: Exploiting the Dual Acid Sites of Metal Organic Framework Catalyst. ChemistrySelect 8:30.
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Farzaneh Mohamadpour. (2022) Visible-light-driven radical Friedländer hetero-annulation of 2-aminoaryl ketone and α-methylene carbonyl compound via organic dye fluorescein through a single-electron transfer (SET) pathway. BMC Chemistry 16:1.
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Farzaneh Mohamadpour. (2022) The development of Friedländer heteroannulation through a single electron transfer and energy transfer pathway using methylene blue (MB+). Scientific Reports 12:1.
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Quyen T. Pham, Phong Q. Le, Ha V. Dang, Hiep Q. Ha, Huong T. D. Nguyen, Thanh Truong & Tri Minh Le. (2020) Iodine-mediated formal [3 + 2] annulation for synthesis of furocoumarin from oxime esters. RSC Advances 10:72, pages 44332-44338.
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Maryam Kargar Karkhah, Hassan Kefayati & Shahab Shariati. (2020) Synthesis of benzo[ h ]quinolone and benzo[ c ]acridinone derivatives by Fe 3 O 4 @ PS‐Arginine [ HSO 4 ] as an efficient magnetic nanocatalyst . Journal of Heterocyclic Chemistry 57:12, pages 4181-4191.
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Moaz M. Abdou, Rasha A. El-Saeed & Samir Bondock. (2019) Recent advances in 4-hydroxycoumarin chemistry. Part 2: Scaffolds for heterocycle molecular diversity. Arabian Journal of Chemistry 12:7, pages 974-1003.
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Mohammad Ali Nasseri, Seyyedeh Ameneh Alavi, Milad Kazemnejadi & Ali Allahresani. (2019) ZrO 2 /SO 4 2− /Cu as a Multifunctional, Durable, Efficient, and Heterogeneous Recoverable Inorgano‐Nanocatalyst for the Green Preparation of Quinolines . ChemistrySelect 4:29, pages 8493-8499.
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Lalit Mohan Nainwal, Sharba Tasneem, Wasim Akhtar, Garima Verma, Mohammed Faraz Khan, Suhel Parvez, Mohammad Shaquiquzzaman, Mymoona Akhter & Mohammad Mumtaz Alam. (2019) Green recipes to quinoline: A review. European Journal of Medicinal Chemistry 164, pages 121-170.
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Genevieve H. Dennison, Jonathan M. White & Martin R. Johnston. (2016) Efficient access to Unsymmetrically 3-Substituted-1,10-Phenanthrolines via Microwave Assisted Friedländer Condensation with Aldehydes.. ChemistrySelect 1:20, pages 6434-6437.
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Federica Bosca, Silvia Tagliapietra, Claudio Garino, Giancarlo Cravotto & Alessandro Barge. (2016) Extensive methodology screening of meso-tetrakys-(furan-2-yl)-porphyrin microwave-assisted synthesis. New Journal of Chemistry 40:3, pages 2574-2581.
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Marina Godino‐Ojer, Antonio J. López‐Peinado, Rosa M. Martín‐Aranda, Jacek Przepiórski, Elena Pérez‐Mayoral & Elena Soriano. (2014) Eco‐Friendly Catalytic Systems Based on Carbon‐Supported Magnesium Oxide Materials for the Friedländer Condensation. ChemCatChem 6:12, pages 3440-3447.
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Parisa Gholamzadeh, Ghodsi Mohammadi Ziarani, Negar Lashgari, Alireza Badiei & Paria Asadiatouei. (2014) Silica functionalized propyl sulfonic acid (SiO2-Pr-SO3H): An efficient catalyst in organic reactions. Journal of Molecular Catalysis A: Chemical 391, pages 208-222.
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Farhad Shirini, Asieh Yahyazadeh, Kamal Mohammadi & Nader Ghaffari Khaligh. (2014) Solvent-free synthesis of quinoline derivatives via the Friedländer reaction using 1,3-disulfonic acid imidazolium hydrogen sulfate as an efficient and recyclable ionic liquid catalyst. Comptes Rendus Chimie 17:4, pages 370-376.
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Prashi Jain, Jiaqin Li, Patrick Porubsky, Benjamin Neuenswander, Susan M. Egan, Jeffrey Aub?Steven Rogers. (2014) 3-Substituted biquinolinium inhibitors of AraC family transcriptional activator VirF from S. flexneri obtained through in situ chemical ionization of 3,4-disubstituted dihydroquinolines. RSC Adv. 4:75, pages 39809.
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Yanfang Zhu & Chun Cai. (2014) An N-heterocyclic carbene-catalyzed approach to the indirect Friedl?nder quinoline synthesis. RSC Adv. 4:95, pages 52911-52914.
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E. Calcio Gaudino, D. Carnaroglio, M. A. G. Nunes, L. Schmidt, E. M. M. Flores, C. Deiana, Y. Sakhno, G. Martra & G. Cravotto. (2014) Fast TiO 2 -catalyzed direct amidation of neat carboxylic acids under mild dielectric heating . Catal. Sci. Technol. 4:5, pages 1395-1399.
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Jesús López‐Sanz, Elena Pérez‐Mayoral, Elena Soriano, Delia Omenat‐Morán, Carlos J. Durán, Rosa María Martín‐Aranda, Ines Matos & Isabel Fonseca. (2013) Acid‐Activated Carbon Materials: Cheaper Alternative Catalysts for the Synthesis of Substituted Quinolines. ChemCatChem 5:12, pages 3736-3742.
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A. Smuszkiewicz, J. L?pez-Sanz, E. P?rez-Mayoral, E. Soriano, I. Sobczak, M. Ziolek, R.M. Mart?n-Aranda & A.J. L?pez-Peinado. (2013) Amino-grafted mesoporous materials based on MCF structure involved in the quinoline synthesis. Mechanistic insights. Journal of Molecular Catalysis A: Chemical 378, pages 38-46.
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Nam T.S. Phan, Tung T. Nguyen, Khoa D. Nguyen & Anh X.T. Vo. (2013) An open metal site metal?organic framework Cu(BDC) as a promising heterogeneous catalyst for the modified Friedl?nder reaction. Applied Catalysis A: General 464-465, pages 128-135.
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Rajender S. Varma. 2001. Kirk-Othmer Encyclopedia of Chemical Technology. Kirk-Othmer Encyclopedia of Chemical Technology 1 68 .
Ghodsi Mohammadi Ziarani & Parvin Hajiabbasi. (2013) Recent Application of 4-Hydroxycoumarin in Multi-Component Reactions. HETEROCYCLES 87:7, pages 1415.
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Rajender S. Varma & R. B. Nasir Baig. 2012. Microwaves in Organic Synthesis. Microwaves in Organic Synthesis 425 486 .
Jesús López-Sanz, Elena Pérez-Mayoral, Elena Soriano, Marina Sturm, Rosa María Martín-Aranda, Antonio J. López-Peinado & Jiří Čejka. (2012) New inorganic–organic hybrid materials based on SBA-15 molecular sieves involved in the quinolines synthesis. Catalysis Today 187:1, pages 97-103.
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Tanmoy Chanda, Rajiv Kumar Verma & Maya Shankar Singh. (2012) InCl 3 ‐Driven Regioselective Synthesis of Functionalized/Annulated Quinolines: Scope and Limitations . Chemistry – An Asian Journal 7:4, pages 778-787.
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Elena Pérez-Mayoral, Zuzana Musilová, Barbara Gil, Bartosz Marszalek, Miroslav Položij, Petr Nachtigall & Jiri Čejka. (2012) Synthesis of quinolines via Friedländer reaction catalyzed by CuBTC metal–organic-framework. Dalton Transactions 41:14, pages 4036.
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Alexander Sachse, Rob Ameloot, Bernard Coq, Fran?ois Fajula, Beno?t Coasne, Dirk De Vos & Anne Galarneau. (2012) In situ synthesis of Cu?BTC (HKUST-1) in macro-/mesoporous silica monoliths for continuous flow catalysis. Chemical Communications 48:39, pages 4749.
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Elena Pérez‐Mayoral & Jiří Čejka. (2010) [Cu 3 (BTC) 2 ]: A Metal–Organic Framework Catalyst for the Friedländer Reaction . ChemCatChem 3:1, pages 157-159.
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Davide Garella, Alessandro Barge, Dharita Upadhyaya, Zalua Rodriguez, Giovanni Palmisano & Giancarlo Cravotto. (2010) ChemInform Abstract: Fast, Solvent‐Free, Microwave‐Promoted Friedlaender Annulation with a Reusable Solid Catalyst.. ChemInform 41:26.
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Margherita Barbero, Stefano Bazzi, Silvano Cadamuro & Stefano Dughera. (2010) o-Benzenedisulfonimide as a reusable Brønsted acid catalyst for an efficient and facile synthesis of quinolines via Friedländer annulation. Tetrahedron Letters 51:17, pages 2342-2344.
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