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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

Al2O3/MeSO3H: A Novel and Recyclable Catalyst for One-Pot Synthesis of 3,4-Dihydropyrimidinones or Their Sulfur Derivatives in Biginelli Condensation

Hashem Sharghi Department of Chemistry, Shiraz University, Shiraz, IranCorrespondence[email protected], [email protected]
&
Mahboubeh Jokar Department of Chemistry, Shiraz University, Shiraz, Iran
Pages 958-979 | Received 12 Aug 2008, Published online: 24 Feb 2009

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Anamika Khaskel, Santosh Kumari Bajiya, Suman Lata, Rakesh Kumar Sharma & Shatabdi Basu. (2023) SbPh3: An Efficient Catalyst for Dihydropyrimidinone and Dihydropyrimidin-5-carboxamide Synthesis Using the Biginelli Reaction. Organic Preparations and Procedures International 55:6, pages 525-537.
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Prerna Ganwir, Kanchan Gavali & Ganesh U. Chaturbhuj. (2023) N-(Phenylsulfonyl)Benzenesulfonamide: A New Organocatalyst for One-Pot, Solvent-Free Synthesis of Biginelli’s 3,4-Dihydropyrimidine-2(1H)-Thiones. Polycyclic Aromatic Compounds 43:4, pages 3182-3191.
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Sharmil N. Anjirwala, Parnas S. Parmar & Saurabh K. Patel. (2022) Synthetic protocols for non-fused pyrimidines. Synthetic Communications 52:22, pages 2079-2121.
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Tukaram S. Choudhare, Devendra S. Wagare, Vijay T. Kadam, Ajit A. Kharpe & Prashant D. Netankar. (2022) Rapid One-Pot Multicomponent Dioxane-HCl Complex Catalyzed Solvent-Free Synthesis of 3,4-Dihydropyrimidine-2-One Derivatives. Polycyclic Aromatic Compounds 42:6, pages 3865-3873.
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Abdullah M. A. Shumaila & Abdulsalam A. N. Al-Thulaia. (2019) Mini-review on the synthesis of Biginelli analogs using greener heterogeneous catalysis: Recent strategies with the support or direct catalyzing of inorganic catalysts. Synthetic Communications 49:13, pages 1613-1632.
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Mallappa Beerappa & Kalegowda Shivashankar. (2018) Synthesis of 4,6-diarylpyrimidin-2(1H)-one derivatives from benzyl halides and (1-bromoethyl)benzene under solvent-free conditions. Synthetic Communications 48:17, pages 2150-2158.
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Karim Akbari Dilmaghani, Behzad Zeynizadeh & Maryam Amirpoor. (2013) Ultrasound-Mediated Synthesis of 3,4-Dihydropyrimidin-2-(1H)-Ones (or Thiones) with NaHSO4·H2O. Phosphorus, Sulfur, and Silicon and the Related Elements 188:11, pages 1634-1642.
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Karim Akbari Dilmaghani, Behzad Zeynizadeh & Hadi Parasajam. (2012) The Efficient Synthesis of 3,4-Dihydropyrimidin-2-(1H)-Ones and Their Sulfur Derivatives with H2SO4 Immobilized on Activated Charcoal. Phosphorus, Sulfur, and Silicon and the Related Elements 187:4, pages 544-553.
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Articles from other publishers (33)

Neamatullah Fekrat, Masoumeh Mazloumi & Farhad Shirini. (2023) Copper salt of a DABCO-based molten salt: a high-performance catalyst in the one-pot synthesis of 3,4-dihydropyrimidine and polyhydroquinoline derivatives. RSC Advances 13:50, pages 35659-35671.
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Vinay Kumar, Rituparna Saha, Satyaki Chatterjee & Vivek Mishra. (2023) From traditional to greener alternatives: potential of plant resources as a biotransformation tool in organic synthesis. Reaction Chemistry & Engineering 8:11, pages 2677-2688.
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Balaji Panchal, Qiaojing Zhao, Bangjun Liu, Yuzhuang Sun, Cunliang Zhao, Kai Bian, Chia-Hung Su & Jinxi Wang. (2023) Surface area and porosity development of catalyst using agricultural waste Chestnut shell biomass as a bio-source for ethyl oleate production. Molecular Catalysis 548, pages 113458.
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Eduardo B. Mass, Carolina A. de Lima, Marcelo G. M. D’Oca, Juliana M. Sciani, Giovanna B. Longato & Dennis Russowsky. (2022) Synthesis, Selective Cytotoxic Activity against Human Breast Cancer MCF7 Cell Line and Molecular Docking of Some Chalcone-Dihydropyrimidone Hybrids. Drugs and Drug Candidates 1:1, pages 3-21.
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Hayedeh Gorjian & Nader Ghaffari Khaligh. (2022) The liquid phase of 4,4'-trimethylenedipiperidine: a safe and greener dual-task agent for clean and facile synthesis of coumarin derivatives. Molecular Diversity 26:6, pages 3047-3055.
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Letcy V. Theresa, Saranya Ponmalakunnu, Anju M. Baby & Krishnapillai Sreekumar. (2021) Ethylene Glycol: Urea: NH 4 Cl Low Melting Mixture‐Assisted Reactions between Aromatic Aldehydes and Active Methylene Compounds . ChemistrySelect 6:28, pages 7150-7157.
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Bing-Jian Yao, Wen-Xiu Wu, Luo-Gang Ding & Yu-Bin Dong. (2021) Sulfonic Acid and Ionic Liquid Functionalized Covalent Organic Framework for Efficient Catalysis of the Biginelli Reaction. The Journal of Organic Chemistry 86:3, pages 3024-3032.
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Lucas L. Zanin & André L. M. Porto. (2020) HClO 4 ‐Al 2 O 3 as a Prominent Catalyst in the Synthesis of 3,4‐Dihydropyrimidin‐2(1 H )‐ones/thiones under Environmentally Friendly Solvent Conditions . ChemistrySelect 5:28, pages 8604-8608.
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Lakha V. Chopda & Pragnesh N. Dave. (2020) Heteropoly-12-tungstophosphoric acid H3[PW12O40] over natural bentonite as a heterogeneous catalyst for the synthesis of 3,4-dihydropyrimidin-2-(1H)-ones. Arabian Journal of Chemistry 13:6, pages 5911-5921.
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Lakha V Chopda & Pragnesh N. Dave. (2020) 12‐Tungstosilicic Acid H 4 [W 12 SiO 40 ] Over Natural Bentonite as a Heterogeneous Catalyst for the Synthesis of 3,4‐dihydropyrimidin‐2(1H)‐Ones . ChemistrySelect 5:8, pages 2395-2400.
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Rajendra V. Patil, Jagdish U. Chavan, Dipak S. Dalal, Vaishali S. Shinde & Anil G. Beldar. (2019) Biginelli Reaction: Polymer Supported Catalytic Approaches. ACS Combinatorial Science 21:3, pages 105-148.
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Hashem Sharghi, Pezhman Shiri & Mahdi Aberi. (2018) An overview on recent advances in the synthesis of sulfonated organic materials, sulfonated silica materials, and sulfonated carbon materials and their catalytic applications in chemical processes. Beilstein Journal of Organic Chemistry 14, pages 2745-2770.
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Hirbod Karimi. (2018) Copper Zirconium Phosphate as an Efficient Catalyst for Multi-component Reactions in Solvent-Free Conditions. Iranian Journal of Science and Technology, Transactions A: Science 42:1, pages 219-235.
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Ali Maleki, Abbas Ali Jafari & Somayeh Yousefi. (2017) MgFe2O4/cellulose/SO3H nanocomposite: a new biopolymer-based nanocatalyst for one-pot multicomponent syntheses of polysubstituted tetrahydropyridines and dihydropyrimidinones. Journal of the Iranian Chemical Society 14:8, pages 1801-1813.
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Hashem Sharghi, Mahdi Aberi & Jasem Aboonajmi. (2016) One-pot synthesis of 2,4-disubstituted quinolines via three-component reaction of amines, aldehydes and alkynes using Al2O3 nanoparticles/methanesulfonic acid (nano-AMA) as a new catalyst. Journal of the Iranian Chemical Society 13:12, pages 2229-2237.
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Flavio A.R. Barbosa, Rômulo F.S. Canto, Sumbal Saba, Jamal Rafique & Antonio L. Braga. (2016) Synthesis and evaluation of dihydropyrimidinone-derived selenoesters as multi-targeted directed compounds against Alzheimer’s disease. Bioorganic & Medicinal Chemistry 24:22, pages 5762-5770.
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Chetan K. Khatri, Deelip S. Rekunge & Ganesh U. Chaturbhuj. (2016) Sulfated polyborate: a new and eco-friendly catalyst for one-pot multi-component synthesis of 3,4-dihydropyrimidin-2(1H)-ones/thiones via Biginelli reaction. New Journal of Chemistry 40:12, pages 10412-10417.
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SANKARANARAYANAN NAGARAJAN, TANVEER M SHAIKH & ELANGO KANDASAMY. (2015) Synthesis of 1-alkyl triazolium triflate room temperature ionic liquids and their catalytic studies in multi-component Biginelli reaction. Journal of Chemical Sciences 127:9, pages 1539-1545.
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SANTOSH KUMAR PRAJAPTI, KESHAV KUMAR GUPTA & BATHINI NAGENDRA BABU. (2015) B(C6F5)3 catalyzed one-pot three-component Biginelli reaction: An efficient and environmentally benign protocol for the synthesis of 3,4-dihydropyrimidin-2(1H)-ones/thiones. Journal of Chemical Sciences 127:6, pages 1047-1052.
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Felipe Vitório, Thiago Moreira Pereira, Rosane Nora Castro, Guilherme Pereira Guedes, Cedric Stephan Graebin & Arthur Eugen Kümmerle. (2015) Synthesis and mechanism of novel fluorescent coumarin–dihydropyrimidinone dyads obtained by the Biginelli multicomponent reaction. New Journal of Chemistry 39:3, pages 2323-2332.
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K. Aswin, S. Sheik Mansoor, K. Logaiya & S.P.N. Sudhan. (2014) Triphenylphosphine: An efficient catalyst for the synthesis of 4,6-diphenyl-3,4-dihydropyrimidine-2(1H)-thione under thermal conditions. Journal of King Saud University - Science 26:2, pages 141-148.
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Rômulo F. S. Canto, Flavio A. R. Barbosa, Vanessa Nascimento, Aldo S. de Oliveira, Inês M. C. Brighente & Antonio Luiz Braga. (2014) Design, synthesis and evaluation of seleno-dihydropyrimidinones as potential multi-targeted therapeutics for Alzheimer's disease. Org. Biomol. Chem. 12:21, pages 3470-3477.
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Ramin Rezaei, Sara Malek, Mohammad Reza Sheikhi & Mohammad Kazem Mohammadi. (2013) Starch Sulfuric Acid: an Alternative, Eco-Friendly Catalyst for Biginelli Reaction. Chemistry Journal of Moldova 8:2, pages 101-106.
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Natália Aparecida Liberto, Sarah de Paiva Silva, Ângelo de Fátima & Sergio Antonio Fernandes. (2013) β-Cyclodextrin-assisted synthesis of Biginelli adducts under solvent-free conditions. Tetrahedron 69:38, pages 8245-8249.
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Fatima-Zohra Akika, Nadjib Kihal, Tahir Habila, Ivalina Avramova, Sefik Suzer, Bernard Pirotte & Smail Khelili. (2013) Synthesis and Characterization of Zn (1-x) Ni x Al 2 O 4 Spinels as a New Heterogeneous Catalyst of Biginelli's Reaction . Bulletin of the Korean Chemical Society 34:5, pages 1445-1453.
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Amulrao Borse, Mahesh Patil, Nilesh Patil & Rohan Shinde. (2012) A Green, Expeditious, One-Pot Synthesis of 3, 4-Dihydropyrimidin-2(1H)-ones Using a Mixture of Phosphorus Pentoxide-Methanesulfonic Acid at Ambient Temperature. ISRN Organic Chemistry 2012, pages 1-6.
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Kawaljit Singh & Kamaljit Singh. 2012. 223 308 .
Ali Khalafi-Nezhad, Abolfath Parhami, Rahele Bargebid, Saghar Molazade, Abdolkarim Zare & Habib Foroughi. (2011) Silica sulfuric acid as mild and efficient catalyst for the preparation of poly-hydroxyl aromatic compounds under mild and heterogeneous conditions. Molecular Diversity 15:2, pages 373-381.
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Suresh Patil, Swati D. Jadhav & Sanjeevani Y. Mane. (2011) Pineapple Juice as a Natural Catalyst: An Excellent Catalyst for Biginelli Reaction. International Journal of Organic Chemistry 01:03, pages 125-131.
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Ganesh Chandra Nandi, Subhasis Samai & Maya Shankar Singh. (2010) Biginelli and Hantzsch-Type Reactions Leading to Highly Functionalized Dihydropyrimidinone, Thiocoumarin, and Pyridopyrimidinone Frameworks via Ring Annulation with β-Oxodithioesters. The Journal of Organic Chemistry 75:22, pages 7785-7795.
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Chennan Ramalingan, Su-Jung Park, In-Sook Lee & Young-Woo Kwak. (2010) A piperidinium triflate catalyzed Biginelli reaction. Tetrahedron 66:16, pages 2987-2994.
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Suryakant B. Sapkal, Kiran F. Shelke, Bapurao B. Shingate & Murlidhar S. Shingare. (2010) Nickel Nanoparticles: An Ecofriendly and Reusable Catalyst for the Synthesis of 3,4-Dihydropyrimidine-2(1H)-ones via Biginelli Reaction. Bulletin of the Korean Chemical Society 31:2, pages 351-354.
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Hashem Sharghi & Mahboubeh Jokar. (2009) ChemInform Abstract: Al 2 O 3 /MeSO 3 H: A Novel and Recyclable Catalyst for One‐Pot Synthesis of 3,4‐Dihydropyrimidinones or Their Sulfur Derivatives in Biginelli Condensation. . ChemInform 40:33.
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