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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 39, 2009 - Issue 4
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Original Articles

Zirconium Tetrakis(dodecyl Sulfate) [Zr(DS)4] as an Efficient Lewis Acid–Surfactant Combined Catalyst for the Synthesis of Quinoxaline Derivatives in Aqueous Media

Alireza Hasaninejad Department of Chemistry, Faculty of Sciences, Persian Gulf University, Bushehr, IranCorrespondence[email protected]
,
Abdolkarim Zare Department of Chemistry, Payame Noor University (PNU), Bushehr, IranCorrespondence[email protected]
,
Mohammad Ali Zolfigol Faculty of Chemistry, Bu-Ali Sina University, Hamedan, Iran
&
Mohsen Shekouhy Department of Chemistry, Faculty of Sciences, Persian Gulf University, Bushehr, Iran
Pages 569-579 | Received 06 Aug 2008, Published online: 27 Jan 2009

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Premkumar B. Thombre, Sonali A. Korde, Sudarshan S. Dipake, Anjali S. Rajbhoj, Machhindra K. Lande & Suresh T. Gaikwad. (2023) A rapid synthesis of quinoxalines by using Al2O3–ZrO2 as heterogeneous catalyst. Synthetic Communications 53:19, pages 1623-1636.
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Alireza Hasaninejad, Mohsen Shekouhy, Marzieh Miar & Somayeh Firoozi. (2016) Sulfonated Polyethylene Glycol (PEG-SO3H) as Eco-Friendly and Potent Water Soluble Solid Acid for Facile and Green Synthesis of 1,8-Dioxo-Octahydroxanthene and 1,8-Dioxo-Decahydroacridine Derivatives. Synthesis and Reactivity in Inorganic, Metal-Organic, and Nano-Metal Chemistry 46:1, pages 151-157.
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Safoura Fathi & Ali Reza Sardarian. (2015) Nitrilotris(Methylenephosphonic Acid) as a New Highly Efficient and Recyclable BrØNested Acid Catalyst for the Synthesis Of Quinoxaline Derivatives under Mild and Green Conditions. Phosphorus, Sulfur, and Silicon and the Related Elements 190:9, pages 1471-1478.
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M. Esmaeilpour & A.R. Sardarian. (2014) Fe3O4@SiO2/Schiff base complex of metal ions as an efficient and recyclable nanocatalyst for the green synthesis of quinoxaline derivatives. Green Chemistry Letters and Reviews 7:3, pages 301-308.
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Frédéric Lassagne, Floris Chevallier & Florence Mongin. (2014) Saccharin as an Organocatalyst for Quinoxalines and Pyrido[2,3-b]pyrazines Syntheses. Synthetic Communications 44:1, pages 141-149.
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Ghasem Rezanejade Bardajee, Farhang Mizani, Iman Rostami & Ali Mohamadi. (2013) FeCl3Mediated Simple, Green, and Efficient Method for the One-Pot Synthesis of Pyrazine-based Polycyclic Aromatic Compounds under Mild Conditions. Polycyclic Aromatic Compounds 33:5, pages 419-429.
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Alireza Hasaninejad, Abdolkarim Zare, Mohammad Reza Mohammadizadeh & Mohsen Shekouhy. (2010) Lithium bromide as an efficient, green, and inexpensive catalyst for the synthesis of quinoxaline derivatives at room temperature. Green Chemistry Letters and Reviews 3:2, pages 143-148.
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Articles from other publishers (43)

Irfan Ali & Rohit Bhatia. (2024) Green and Eco-friendly Synthetic Strategies for Quinoxaline Derivatives. Current Green Chemistry 11:1, pages 37-49.
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Rangappa S. Keri, Dinesh Reddy, Srinivasa Budagumpi & Vinayak Adimule. (2023) Reusable nano-catalyzed green protocols for the synthesis of quinoxalines: an overview. RSC Advances 13:29, pages 20373-20406.
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Mehdi Kalhor, Mahboubeh Shayestefar, Mehdi Khalaj & Fatemeh Janghorban. (2022) Ca(IO3)2 nanoparticles: fabrication and application as an eco-friendly and recyclable catalyst for the green synthesis of quinoxalines, pyridopyrazines, and 2,3-dicyano pyrazines. Research on Chemical Intermediates 49:3, pages 885-900.
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M. Bharathi, S. Mathivathani, S. Indira, G. Vinoth, Denzil Britto Christopher Leslee & K. Shanmuga Bharathi. (2023) Anchoring of a nickel Schiff base complex with mixed ligands on MCM-41 as a heterogeneous catalyst for the synthesis of quinoxaline derivatives by various energies. Polyhedron 229, pages 116188.
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Fabián Amaya-García & Miriam M. Unterlass. (2022) Synthesis of 2,3-Diarylquinoxaline Carboxylic Acids in High-Temperature Water. Synthesis 54:15, pages 3367-3382.
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Prasun Choudhury & Basudeb Basu. 2021. Green Synthetic Approaches for Biologically Relevant Heterocycles. Green Synthetic Approaches for Biologically Relevant Heterocycles 689 768 .
Karim Dânoun, Younes Essamlali, Othmane Amadine, Hassan Mahi & Mohamed Zahouily. (2020) Eco-friendly approach to access of quinoxaline derivatives using nanostructured pyrophosphate Na2PdP2O7 as a new, efficient and reusable heterogeneous catalyst. BMC Chemistry 14:1.
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Ruby Singh, Diksha Bhardwaj, Shakeel Ahmad Ganaie & Aakash Singh. (2020) Lewis Acid Surfactant Combined (LASC) Catalyst as a Versatile Heterogeneous Catalyst in Various Organic Transformations. Mini-Reviews in Organic Chemistry 17:2, pages 124-140.
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Bubun Banerjee. 2020. Green Sustainable Process for Chemical and Environmental Engineering and Science. Green Sustainable Process for Chemical and Environmental Engineering and Science 153 190 .
Afsaneh Rashidizadeh, Hossein Ghafuri, Hamid Reza Esmaili Zand & Nahal Goodarzi. (2019) Graphitic Carbon Nitride Nanosheets Covalently Functionalized with Biocompatible Vitamin B 1 : Synthesis, Characterization, and Its Superior Performance for Synthesis of Quinoxalines . ACS Omega 4:7, pages 12544-12554.
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Sourav De, Bidisha Sarkar, Gajanan Raosaheb Jadhav, Selva Kumar Ramasamy, Subhasis Banerjee, Anbalagan Moorthy, Priyankar Paira & Ashok Kumar S K. (2018) Experimental and Theoretical Study on the Biomolecular Interaction of Novel Acenaphtho Quinoxaline and Dipyridophenazine Analogues. ChemistrySelect 3:38, pages 10593-10602.
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KRISHNA S INDALKAR, CHETAN K KHATRI & GANESH U CHATURBHUJ. (2017) Rapid, efficient and eco-friendly procedure for the synthesis of quinoxalines under solvent-free conditions using sulfated polyborate as a recyclable catalyst. Journal of Chemical Sciences 129:2, pages 141-148.
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Maasoumeh Jafarpour & Abdolreza Rezaeifard. (2015) A zirconium Schiff base complex immobilized on starch-coated maghemite nanoparticles catalyzes heterogeneous condensation of 1,2-diamines with 1,2-dicarbonyl compounds. Transition Metal Chemistry 41:2, pages 205-211.
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Vakhid A. MamedovVakhid A. Mamedov. 2016. Quinoxalines. Quinoxalines 5 133 .
Seyed Meysam Baghbanian. (2015) Propylsulfonic acid functionalized nanozeolite clinoptilolite as heterogeneous catalyst for the synthesis of quinoxaline derivatives. Chinese Chemical Letters 26:9, pages 1113-1116.
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Marzieh Mohammadi, Ghasem Rezanejade Bardajee & Nader Noroozi Pesyan. (2015) Efficient solvent-free synthesis of pyridopyrazine and quinoxaline derivatives using copper-DiAmSar complex anchored on SBA-15 as a reusable catalyst. Chinese Journal of Catalysis 36:8, pages 1379-1386.
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Yansheng Dong, Li Huang & Fengping Yi. (2015) Iodine-Mediated Efficient Synthesis of 2,3-Dihydro-Pyrazines. Journal of Chemical Research 39:7, pages 430-432.
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Mohsen Shekouhy & Ali Khalafi-Nezhad. (2015) Polyethylene glycol-bonded 1,8-diazabicyclo[5.4.0]undec-7-ene (PEG–DBU) as a surfactant-combined base catalyst for the application of nucleosides as reagents in multi-component syntheses of 8-substituted pyrido[2,3-d]pyrimidine-6-carbonitriles in water. Green Chemistry 17:10, pages 4815-4829.
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Basudeb Basu & Bablee Mandal. 2015. Green Synthetic Approaches for Biologically Relevant Heterocycles. Green Synthetic Approaches for Biologically Relevant Heterocycles 209 256 .
Swati Samanta, Arpita Das Gupta & Asok K. Mallik. (2014) An expedient “on-water” synthesis of quinoxalines. Monatshefte für Chemie - Chemical Monthly 145:10, pages 1669-1673.
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Hamid Reza Safaei, Mohsen Shekouhy, Shima Khademi, Vahid Rahmanian & Maryam Safaei. (2014) Diversity-oriented synthesis of quinazoline derivatives using zirconium tetrakis(dodecylsulfate) [Zr(DS)4] as a reusable Lewis acid-surfactant-combined catalyst in tap water. Journal of Industrial and Engineering Chemistry 20:5, pages 3019-3024.
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Lijiu Gao, Rui Liu, Chenxia Yu, Changsheng Yao, Tuanjie Li & Zhaoxin Xiao. (2013) NHC-initiated cascade, metal-free synthesis of quinoxaline derivatives under solvent-free conditions. Research on Chemical Intermediates 40:5, pages 2131-2138.
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Naushad Edayadulla & Yong Rok Lee. (2014) Cerium oxide nanoparticle-catalyzed three-component protocol for the synthesis of highly substituted novel quinoxalin-2-amine derivatives and 3,4-dihydroquinoxalin-2-amines in water. RSC Advances 4:22, pages 11459.
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Maasoumeh Jafarpour, Elham Rezapour, Mahboobe Ghahramaninezhad & Abdolreza Rezaeifard. (2014) A novel protocol for selective synthesis of monoclinic zirconia nanoparticles as a heterogeneous catalyst for condensation of 1,2-diamines with 1,2-dicarbonyl compounds. New J. Chem. 38:2, pages 676-682.
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Pradeep S. Jadhavar, Dinesh Kumar, Priyank Purohit, Bhavin V. Pipaliya, Asim Kumar, Srikant Bhagat & Asit K. Chakraborti. 2014. Green Chemistry: Synthesis of Bioactive Heterocycles. Green Chemistry: Synthesis of Bioactive Heterocycles 37 67 .
Alireza Hasaninejad & Somayeh Firoozi. (2013) Catalyst-free, one-pot, three-component synthesis of 5-amino-1,3-aryl-1 $$H$$ -pyrazole-4-carbonitriles in green media. Molecular Diversity 17:3, pages 459-469.
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Reihaneh Malakooti, Ghasem Rezanejade Bardajee, Hesamaldin Mahmoudi & Nahale Kakavand. (2013) Zirconium Schiff-Base Complex Modified Mesoporous Silica as an Efficient Catalyst for the Synthesis of Nitrogen Containing Pyrazine Based Heterocycles. Catalysis Letters 143:8, pages 853-861.
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Alireza Hasaninejad, Nooshin Golzar & Abdolkarim Zare. (2013) One-Pot, Four-Component Synthesis of Novel Spiro[indeno[2,1- b ]quinoxaline-11,4′-pyran]-2′-amines . Journal of Heterocyclic Chemistry 50:3, pages 608-614.
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Tie‐Qiang Huang, Wen‐Yan Qu, Jin‐Chang Ding, Miao‐Chang Liu, Hua‐Yue Wu & Jiu‐Xi Chen. (2013) Catalyst‐Free Protocol for the Synthesis of Quinoxalines and Pyrazines in PEG. Journal of Heterocyclic Chemistry 50:2, pages 293-297.
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Hari K. Kadam, Salman Khan, Rupesh A. Kunkalkar & Santosh G. Tilve. (2013) Graphite catalyzed green synthesis of quinoxalines. Tetrahedron Letters 54:8, pages 1003-1007.
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Maasoumeh Jafarpour, Abdolreza Rezaeifard, Reza Haddad & Somayeh Gazkar. (2012) A reusable zirconium(IV) Schiff base complex catalyzes highly efficient synthesis of quinoxalines under mild conditions. Transition Metal Chemistry 38:1, pages 31-36.
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Dinesh Kumar, Kapileswar Seth, Damodara N. Kommi, Srikant Bhagat & Asit K. Chakraborti. (2013) Surfactant micelles as microreactors for the synthesis of quinoxalines in water: scope and limitations of surfactant catalysis. RSC Advances 3:35, pages 15157.
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Alireza Hasaninejad, Mohsen Shekouhy & Abdolkarim Zare. (2012) Silicananoparticles efficiently catalyzed synthesis of quinolines and quinoxalines. Catal. Sci. Technol. 2:1, pages 201-214.
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Vakhid A. Mamedov & Nataliya A. Zhukova. 2012. 55 88 .
Alireza Hasaninejad, Nooshin Golzar, Mohsen Shekouhy & Abdolkarim Zare. (2011) Diversity‐Oriented Synthesis of Novel 2′‐Aminospiro[11 H ‐indeno[1,2‐ b ]quinoxaline‐11,4′‐[4 H ]pyran] Derivatives via a One‐Pot Four‐Component Reaction . Helvetica Chimica Acta 94:12, pages 2289-2294.
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Alireza Hasaninejad, Mohsen Shekouhy, Nooshin Golzar, Abdolkarim Zare & Mohammad Mahdi Doroodmand. (2011) Silica bonded n-propyl-4-aza-1-azoniabicyclo[2.2.2]octane chloride (SB-DABCO): A highly efficient, reusable and new heterogeneous catalyst for the synthesis of 4H-benzo[b]pyran derivatives. Applied Catalysis A: General 402:1-2, pages 11-22.
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Chandrasekhar Navuluri. 2001. Encyclopedia of Reagents for Organic Synthesis. Encyclopedia of Reagents for Organic Synthesis.
Jun Li, Dan‐Na Jiang, Jiu‐Xi Chen, Miao‐Chang Liu, Jin‐Chang Ding & Hua‐Yue Wu. (2011) Eco‐friendly synthesis of quinoxaline derivatives by grinding under solvent‐free conditions. Journal of Heterocyclic Chemistry 48:2, pages 403-406.
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Jun‐Tao Hou, Yong‐Hui Liu & Zhan‐Hui Zhang. (2010) NbCl 5 as an efficient catalyst for rapid synthesis of quinoxaline derivatives . Journal of Heterocyclic Chemistry 47:3, pages 703-706.
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Kioumars Aghapoor, Hossein Reza Darabi, Farshid Mohsenzadeh, Yadollah Balavar & Hesam Daneshyar. (2009) Zirconium(IV) chloride as versatile catalyst for the expeditious synthesis of quinoxalines and pyrido[2,3-b]pyrazines under ambient conditions. Transition Metal Chemistry 35:1, pages 49-53.
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Abdolkarim Zare, Alireza Hasaninejad, Abolfath Parhami, Ahmad Moosavi-ZareRezaReza, Fatemeh Khedri, Zahra Parsaee, Maasoomeh Abdolalipoor-Saretoli, Maasoomeh Khedri, Mehrnoosh Roshankar & Hanafieh Deisi. (2010) Ionic liquid 1-butyl-3-methylimidazolium bromide ([bmim]Br): A green and neutral reaction media for the efficient, catalyst-free synthesis of quinoxaline derivatives. Journal of the Serbian Chemical Society 75:10, pages 1315-1324.
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Hong-Yan Lü, Shu-Hong Yang, Jia Deng & Zhan-Hui Zhang. (2010) Magnetic Fe3O4 Nanoparticles as New, Efficient, and Reusable Catalysts for the Synthesis of Quinoxalines in Water. Australian Journal of Chemistry 63:8, pages 1290.
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Alireza Hasaninejad, Abdolkarim Zare, Mohammad Ali Zolfigol & Mohsen Shekouhy. (2009) ChemInform Abstract: Zirconium Tetrakis(dodecyl Sulfate) [Zr(DS) 4 ] as an Efficient Lewis Acid—Surfactant Combined Catalyst for the Synthesis of Quinoxaline Derivatives in Aqueous Media. . ChemInform 40:32.
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