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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 33, 2003 - Issue 9
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Original Articles

Lanthanide Triflate Catalyzed One-Pot Synthesis of Dihydropyrimidin-2(1H)-thiones by a Three-Component of 1,3-Dicarbonyl Compounds, Aldehydes, and Thiourea Using a Solvent-Free Biginelli Condensation

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Pages 1459-1468 | Received 09 Apr 2002, Published online: 16 Aug 2006

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Read on this site (10)

Heshmatollah Alinezhad & Khatereh Pakzad. (2020) Green Synthesis of Copper Oxide Nanoparticles with an Extract of Euphorbia maculata and Their Use in the Biginelli Reaction. Organic Preparations and Procedures International 52:4, pages 319-327.
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Mahmood Kamali, Abbas Shockravi, Maryam Saghafi Doost & Seyyed Emad Hooshmand. (2015) One-pot, solvent-free synthesis via Biginelli reaction: Catalyst-free and new recyclable catalysts. Cogent Chemistry 1:1.
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B. Suresh Kuarm, J. Venu Madhav, S. Vijaya Laxmi & B. Rajitha. (2012) Xanthan Sulfuric Acid: A New and Efficient Biosupported Solid Acid Catalyst for the Synthesis of 3,4-Dihydropyrimidin-2(1H)-Ones. Synthetic Communications 42:8, pages 1211-1217.
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Ming Lei, Dong-Dong Wu, He-Geng Wei & Yan-Guang Wang. (2009) Polymer-Supported 4-Aminoformoyldiphenylammonium Triflate (PS-AFDPAT): An Effective and Recyclable Catalyst for the Biginelli Reaction. Synthetic Communications 39:3, pages 475-483.
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Feng Xu, Jian‐Jun Wang & You‐Ping Tian. (2008) New Procedure for One‐Pot Synthesis of 3,4‐Dihydropyrimidin‐2(1H)‐ones by Biginelli Reaction. Synthetic Communications 38:8, pages 1299-1310.
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Renwei Zheng, Xiaoxia Wang, Hui Xu & Jingxing Du. (2006) Brønsted Acidic Ionic Liquid: An Efficient and Reusable Catalyst for the Synthesis of 3,4‐Dihydropyrimidin‐2(1H)‐ones. Synthetic Communications 36:11, pages 1503-1513.
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Adrienn Hegedüs, Zoltán Hell & Ilona Vígh. (2006) Convenient One‐Pot Heterogeneous Catalytic Method for the Preparation of 3,4‐Dihydropyrimidin‐2(1H)‐ones. Synthetic Communications 36:1, pages 129-136.
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Limin Wang, Jia Sheng, He Tian & Changtao Qian. (2004) An Efficient Procedure for the Synthesis of Benzimidazole Derivatives Using Yb(OTf)3 as Catalyst Under Solvent‐Free Conditions. Synthetic Communications 34:23, pages 4265-4272.
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Articles from other publishers (37)

Netra Prasad Neupane, Yuan-Seng Wu & Amita Verma. 2023. Dihydropyrimidinones as Potent Anticancer Agents. Dihydropyrimidinones as Potent Anticancer Agents 1 15 .
Onorato Campopiano, David J. JeanJrJr & Liam T. Ball. 2001. Encyclopedia of Reagents for Organic Synthesis. Encyclopedia of Reagents for Organic Synthesis 1 3 .
Nilesh S. Pawar, Pramod N. Patil & Rajashri N. Pachpande. (2022) An Efficient Synthesis and Antibacterial Activity of Some Novel 3,4–Dihydropyrimidin-2-(1H)-Ones. An Efficient Synthesis and Antibacterial Activity of Some Novel 3,4–Dihydropyrimidin-2-(1H)-Ones.
Sourav Handique & Priyanka Sharma. (2022) One pot three components solvent free synthesis of 4-substituted phenyl-2-(sulfanyl/oxo) pyrimidine-5-carboxylate derivatives. Results in Chemistry 4, pages 100411.
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Nandkishor D. Gawhale, Mahendra N. Lokhande, Santosh J. Uke, Satish P. Mardikar, Vikram U. Pandit & Manisha M. Kodape. (2022) An expedient synthesis of 3,4-dihydropyrimidin-2(1H)-ones derivatives under solvent free condition using titanium dioxide as a catalyst. Materials Today: Proceedings 53, pages 191-195.
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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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C.E. Torres-Méndez & B. López-Mayorga. (2020) Copper supported on acid-activated vermiculite as an efficient and recyclable catalyst for the Biginelli reaction: a green approach. Clay Minerals 55:4, pages 271-280.
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Vimal Kumar Madduluri, Santosh Kumar Mishra & Ajay K. Sah. (2020) Synthesis and catalytic application of d-glucose derived ytterbium(III) complex in Biginelli reaction. Inorganic Chemistry Communications 120, pages 108165.
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Mariana Matias, Gonçalo Campos, Adriana O. Santos, Amílcar Falcão, Samuel Silvestre & Gilberto Alves. (2019) Synthesis, in vitro evaluation and QSAR modelling of potential antitumoral 3,4-dihydropyrimidin-2-(1H)-thiones. Arabian Journal of Chemistry 12:8, pages 5086-5102.
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Elham Dezfoolinezhad, Keivan Ghodrati & Rashid Badri. (2018) Polyionene/Br3 Grafted on Magnetic Nanoparticles as an Efficient and Eco-Friendly Catalyst for the Metal Free Synthesis of 3,4-Dihydropyrimidin-2(1H)-Ones/Thiones. Silicon 11:3, pages 1593-1609.
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G. N. Badalova, V. M. Abbasov, I. A. Valiyev, L. I. Alieva & A. H. Talybov. (2017) 1-Methyl-2-oxopyrrolidinium perchlorate ionic liquid in synthesis of 5-ethoxycarbonyl-3,4-dihydropyrimidin-2(1H)-ones. Russian Journal of General Chemistry 87:11, pages 2739-2743.
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Manuela Oliverio, Paola Costanzo, Monica Nardi, Ivan Rivalta & Antonio Procopio. (2014) Facile Ecofriendly Synthesis of Monastrol and Its Structural Isomers via Biginelli Reaction. ACS Sustainable Chemistry & Engineering 2:5, pages 1228-1233.
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Parvez Ali, Naziyanaz Pathan & Taibi Ben Hadda. (2014) Benign Methodology and Efficient Catalysis for the One-Pot Multicomponent Synthesis of Dihydropyrimidinones and Thiones: A New Key for Old Lock. Journal of Applied Chemistry 2014, pages 1-6.
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David M. Arnold, Matthew G. LaPorte, Shelby M. Anderson & Peter Wipf. (2013) Condensation reactions of guanidines with bis-electrophiles: formation of highly nitrogenous heterocycles. Tetrahedron 69:36, pages 7719-7731.
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Kawaljit Singh & Kamaljit Singh. 2012. 223 308 .
Chandran Raju, R. Uma, Kalaipriya Madhaiyan, Radhakrishnan Sridhar & Seeram Ramakrishna. (2011) Ammonium Trifluoroacetate-Mediated Synthesis of 3,4-dihydropyrimidin-2(1 H )-ones . ISRN Organic Chemistry 2011, pages 1-5.
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Davood Azarifar, Kaveh Khosravi, Khadijeh Soleimani & Zohreh Najminejad. (2011) Microwave-assisted solvent-free synthesis of 3,4-dihydropyrimidin-2(1H)-ones catalyzed by NH4OBr. Collection of Czechoslovak Chemical Communications 76:8, pages 989-995.
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Zerong Wang. 2010. Comprehensive Organic Name Reactions and Reagents. Comprehensive Organic Name Reactions and Reagents 9 12 .
. (2009) NiSO 4 ·7H 2 O : An Efficient and Eco-friendly Catalyst for the One-pot Synthesis of Dihydropyrimidin-2(1H)-ones . Journal of the Korean Chemical Society 53:1, pages 90-94.
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Maksim A. Kolosov, Valeriy D. Orlov, Dmitriy A. Beloborodov & Victor V. Dotsenko. (2008) A chemical placebo: NaCl as an effective, cheapest, non-acidic and greener catalyst for Biginelli-type 3,4-dihydropyrimidin-2(1H)-ones (-thiones) synthesis. Molecular Diversity 13:1, pages 5-25.
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Hojatollah Khabazzadeh, Kazem Saidi & Hassan Sheibani. (2008) Microwave-assisted synthesis of dihydropyrimidin-2(1H)-ones using graphite supported lanthanum chloride as a mild and efficient catalyst. Bioorganic & Medicinal Chemistry Letters 18:1, pages 278-280.
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Juan Carlos Rodríguez-Domínguez, Dan Bernardi & Gilbert Kirsch. (2007) ZrCl4 or ZrOCl2 under neat conditions: optimized green alternatives for the Biginelli reaction. Tetrahedron Letters 48:33, pages 5777-5780.
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Atul Kumar & Ram Awatar Maurya. (2007) Synthesis of 3,4-dihydropyrimidin-2(1H)-ones using Ziegler–Natta catalyst system under solvent free conditions. Journal of Molecular Catalysis A: Chemical 272:1-2, pages 53-56.
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Atul Kumar & Ram Awatar Maurya. (2007) An efficient bakers’ yeast catalyzed synthesis of 3,4-dihydropyrimidin-2-(1H)-ones. Tetrahedron Letters 48:26, pages 4569-4571.
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Javad Azizian, Ali A. Mohammadi, M. Kohshari, Ali R. Karimi & Mohammad R. Mohammadizadeh. (2009) Biginelli‐like three component reaction: Synthesis of some new ethyl 6‐ethoxycarbonylmethyl‐4‐aryl‐2‐oxo‐1,2,3,4‐tetrahydropyrimidine‐5‐carboxylate derivatives. Journal of Heterocyclic Chemistry 44:2, pages 455-458.
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D. M. Pore, U. V. Desai, T. S. Thopate & P. P. Wadgaonkar. (2007) Anhydrous Magnesium Sulfate Mediated Solvent-Free Synthesis of Dihydropyrimidin-2(1H)-ones at Ambient Temperature. Australian Journal of Chemistry 60:6, pages 435.
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Ming Li, Wei-Si Guo, Li-Rong Wen, Ya-Feng Li & Hua-Zheng Yang. (2006) One-pot synthesis of Biginelli and Hantzsch products catalyzed by non-toxic ionic liquid (BMImSac) and structural determination of two products. Journal of Molecular Catalysis A: Chemical 258:1-2, pages 133-138.
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Onorato Campopiano & David J. St. JeanJr.Jr.. 2001. Encyclopedia of Reagents for Organic Synthesis. Encyclopedia of Reagents for Organic Synthesis.
Li-Min Wang, Jue-Hua Shao, He Tian, Yong-Hong Wang & Bo Liu. (2006) Rare earth perfluorooctanoate [RE(PFO)3] catalyzed one-pot synthesis of benzopyran derivatives. Journal of Fluorine Chemistry 127:1, pages 97-100.
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Weike Su, Jianjun Li, Zhiguo Zheng & Yinchu Shen. (2005) One-pot synthesis of dihydropyrimidiones catalyzed by strontium(II) triflate under solvent-free conditions. Tetrahedron Letters 46:36, pages 6037-6040.
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Ivica Cepanec, Mladen Litvić, Anamarija Bartolinčić & Marija Lovrić. (2005) Ferric chloride/tetraethyl orthosilicate as an efficient system for synthesis of dihydropyrimidinones by Biginelli reaction. Tetrahedron 61:17, pages 4275-4280.
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E. S. Putilova, G. V. Kryshtal’, G. M. Zhdankina, N. A. Troitskii & S. G. Zlotin. (2005) Alkylammonium and Alkylimidazolium Perhaloborates, Phosphates, and Aluminates as Catalysts in the Biginelli Reaction. Russian Journal of Organic Chemistry 41:4, pages 512-516.
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Xiaoyan Han, Fan Xu, Yiqin Luo & Qi Shen. (2005) An Efficient One‐Pot Synthesis of Dihydropyrimidinones by a Samarium Diiodide Catalyzed Biginelli Reaction Under Solvent‐Free Conditions. European Journal of Organic Chemistry 2005:8, pages 1500-1503.
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Limin Wang, Jijun Liu, He Tian, Changtao Qian & Jie Sun. (2005) One-Pot Synthesis ofcis-Isoquinolonic Acid Derivativesvia Three-Component Reaction of Homophthalic Anhydride with Aldehydes and Amines using Ytterbium(III) Triflate as Catalyst. Advanced Synthesis & Catalysis 347:5, pages 689-694.
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Li-Min Wang, Jia Sheng, Liang Zhang, Jian-Wei Han, Zhao-Yu Fan, He Tian & Chang-Tao Qian. (2005) Facile Yb(OTf)3 promoted one-pot synthesis of polyhydroquinoline derivatives through Hantzsch reaction. Tetrahedron 61:6, pages 1539-1543.
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M. Adharvana Chari & K. Syamasundar. (2004) Silicagel supported sodium hydrogensulfate as a heterogenous catalyst for high yield synthesis of 3,4-dihydropyrimidin-2 (1H)-ones. Journal of Molecular Catalysis A: Chemical 221:1-2, pages 137-139.
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Limin Wang, Changtao Qian, He Tian & Yun Ma. (2003) Lanthanide Triflate Catalyzed One‐Pot Synthesis of Dihydropyrimidin‐2(1H)‐thiones by a Three‐Component of 1,3‐Dicarbonyl Compounds, Aldehydes, and Thiourea Using a Solvent‐Free Biginelli Condensation.. ChemInform 34:34.
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