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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 30, 2000 - Issue 12
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Original Articles

3,4-Dihydropyrimidin-2(1H)-Ones: Fast Synthesis Under Microwave Irradiation in Solvent Free Conditions

Hélio A. Stefani Departamento de Farmácia, Faculdade de Ciěncias Farmacěuticas, Universidade de São Paulo, São Paulo, SP, Brasil E-mail: [email protected]
&
Paula M. Gatti Departamento de Farmácia, Faculdade de Ciěncias Farmacěuticas, Universidade de São Paulo, São Paulo, SP, Brasil E-mail: [email protected]
Pages 2165-2173 | Received 10 Jun 1999, Published online: 04 Dec 2007

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Navjeet Kaur, Kirti Sharma & Pooja Grewal. (2022) Synthesis of heterocycles from urea and its derivatives. Synthetic Communications 52:19-20, pages 1867-1899.
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H. Valizadeh, H. Gholipur, R. Zarrebin, M. Amiri & M.R. Sabzi. (2008) Titanium(IV) Chloride Catalyzed One-Pot Synthesis of 3,4-Dihydropyrimidin-2-(1h)-ones under Solvent-Free Conditions via Three-Component Biginelli Reaction. Phosphorus, Sulfur, and Silicon and the Related Elements 183:7, pages 1552-1555.
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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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M. Syamala. (2005) A DECADE OF ADVANCES IN THREE-COMPONENT REACTIONS. Organic Preparations and Procedures International 37:2, pages 103-171.
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Ahmad Shaabani, Ayoob Bazgir & Sakineh Arab-Ameri. (2004) TETRABUTYLAMMONIUM HYDROGEN SULFATE: AN EFFICIENT CATALYST FOR THE SYNTHESIS OF 3,4-DIHYDROPYRIMIDIN-2(1H)-ONES UNDER SOLVENT-FREE CONDITIONS. Phosphorus, Sulfur, and Silicon and the Related Elements 179:11, pages 2169-2175.
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Yulin Zhu, Yuanjiang Pan & Shenlin Huang. (2004) Trimethylsilyl Chloride: A Facile and Efficient Reagent for One‐Pot Synthesis of 3,4‐Dihydropyrimidin‐2(1H)‐ones. Synthetic Communications 34:17, pages 3167-3174.
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Tong‐Shou Jin, Huan‐Xin Wang, Chun‐Yong Xing, Xiao‐Liu Li & Tong‐Shuang Li. (2004) An Efficient One‐Pot Synthesis of 3,4‐Dihydropyrimidin‐2‐ones Catalyzed by Methanesulfonic Acid. Synthetic Communications 34:16, pages 3009-3016.
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Shu-Jiang Tu, Jian-Feng Zhou, Pei-Jun Cai, Hai Wang & Jun-Cai Feng. (2002) A CONVENIENT FERRIC CHLORIDE CATALYZED SYNTHESIS OF 5-ALKOXYCARBONYL-4-ARYL-3,4-DIHYDROPYRIMIDIN-2(1H)-ONES UNDER MICROWAVE IRRADIATION. Synthetic Communications 32:1, pages 147-151.
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Articles from other publishers (42)

Yasser M. Zohny, Samir M. Awad, Maha A. Rabie & Omar A. Al-Saidan. (2023) Synthesis of Dihydropyrimidines: Isosteres of Nifedipine and Evaluation of Their Calcium Channel Blocking Efficiency. Molecules 28:2, pages 784.
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Adarsh Kumar, Ankit Kumar Singh, Veena Vijayan, Harshwardhan Singh, Amita Verma & Pradeep Kumar. 2023. Dihydropyrimidinones as Potent Anticancer Agents. Dihydropyrimidinones as Potent Anticancer Agents 67 101 .
Shaik Khasimbi, Faraat Ali, Kiran Manda, Anjali Sharma, Garima Chauhan & Sharad Wakode. (2021) Dihydropyrimidinones Scaffold as a Promising Nucleus for Synthetic Profile and Various Therapeutic Targets: A Review. Current Organic Synthesis 18:3, pages 270-293.
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Bipin Shinde, Santosh Kamble, Pramod Gaikwad, Vishvanath Ghanwat, Sagar Tanpure, Pavan Pagare, Bhausaheb Karale & Arvind Burungale. (2018) Novel catalytic application of Ni@ZnO nanoparticles and ZnO nanoflakes in aqueous solution of NaPTS hydrotrope at room temperature via a green synthesis of 3,4-dihydropyrimidin-2(1H)-ones. Research on Chemical Intermediates 44:5, pages 3097-3113.
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Zhi-Lei Zhou, Peng-Cheng Wang & Ming Lu. (2016) Bronsted acidic ionic liquid [C 3 SO 3 HDoim]HSO 4 catalyzed one-pot three-component Biginelli-type reaction: An efficient and solvent-free synthesis of pyrimidinone derivatives and its mechanistic study. Chinese Chemical Letters 27:2, pages 226-230.
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Vanitha Ramachandran, Karthiga Arumugasamy, Sanjeev Kumar Singh, Naushad Edayadulla, Penugonda Ramesh & Sathish-Kumar Kamaraj. (2015) Synthesis, antibacterial studies, and molecular modeling studies of 3,4-dihydropyrimidinone compounds. Journal of Chemical Biology 9:1, pages 31-40.
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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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Tilak Raj, Beant Kaur Billing, Navneet Kaur & Narinder Singh. (2015) Design, synthesis and antimicrobial evaluation of dihydropyrimidone based organic–inorganic nano-hybrids. RSC Advances 5:58, pages 46654-46661.
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K. Venkatesan, V. S. V. Satyanarayana & A. Sivakumar. (2014) Ultrasound‐Assisted Synthesis of 6‐Methyl‐1,2,3,4‐tetrahydro‐ N ‐aryl‐2‐oxo/thio‐4‐arylpyrimidine‐5‐carboxamides Catalyzed by Uranyl Nitrate Hexahydrate . Journal of the Chinese Chemical Society 61:6, pages 624-630.
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Qing Chen, Qingjian Liu & Haiping Wang. (2012) Methyl 6-Methyl-1-(4-methylphenyl)-2-oxo-4-phenyl-1,2,3,4-tetrahydropyrimidine-5-carboxylate. Molbank 2012:2, pages M752.
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DHANAJI V JAWALE, UMESH R PRATAP, APARNA A MULAY, JYOTIRLING R MALI & RAMRAO A MANE. (2011) Synthesis of New dihydropyrimidinones catalysed by dicationic ionic liquid. Journal of Chemical Sciences 123:5, pages 645-655.
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Zerong Wang. 2010. Comprehensive Organic Name Reactions and Reagents. Comprehensive Organic Name Reactions and Reagents 9 12 .
Sergey V. Ryabukhin, Andrey S. Plaskon, Semen S. Bondarenko, Eugeniy N. Ostapchuk, Oleksandr O. Grygorenko, Oleg V. Shishkin & Andrey A. Tolmachev. (2010) Acyl pyruvates as synthons in the Biginelli reaction. Tetrahedron Letters 51:32, pages 4229-4232.
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Choorikkat Ranjith, G V Srinivasan & K K Vijayan. (2010) Tributyl Borate Mediated Biginelli Reaction: A Facile Microwave-Assisted Green Synthetic Strategy toward Dihydropyrimidinones. Bulletin of the Chemical Society of Japan 83:3, pages 288-290.
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Vinod Tribhuvannathji Kamble, Dnyanoba Baburao Muley, Sandeep Tukaram Atkore & Sharad Digambarrao Dakore. (2010) Three Component Reaction: An Efficient Synthesis of 3,4‐Dihydropyrimidin‐2(1 H )‐ones and Thiones Using Heterogeneous Catalyst . Chinese Journal of Chemistry 28:3, pages 388-392.
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M. Saranga Pani, M. Arjun, D. Sridhar, K. Srinivas & T. Raviprasad. (2009) N-Substituted benzoxazolyl ureas and thioureas in Biginelli reaction promoted by trifluoromethane sulfonic acid: An efficient and convenient synthesis of substituted benzoxazolyl 3,4-dihydropyrimidine (1H)-(thio)-ones. Chinese Chemical Letters 20:8, pages 909-912.
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Nuno R. Candeias, Luís C. Branco, Pedro M. P. Gois, Carlos A. M. Afonso & Alexandre F. Trindade. (2009) More Sustainable Approaches for the Synthesis of N-Based Heterocycles. Chemical Reviews 109:6, pages 2703-2802.
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. (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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. (2008) Synthesis of 3,4-Dihydropyrimidin-2(1H)-ones Using HClO 4 -SiO 2 as a Heterogeneous and Recyclable Catalyst . Bulletin of the Korean Chemical Society 29:9, pages 1752-1754.
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Maurício Vega-Teijido, Julio Zukerman-Schpector, Fábio Macedo Nunes, Paula M. Gatti, Hélio Alexandre Stefani & Ignez Caracelli. (2007) Crystal and molecular structures of 4-substituted 3,4-dihydropyrimidin-2(1H)-ones studied by X-ray and AM1 and B3LYP calculations. Zeitschrift für Kristallographie - Crystalline Materials 222:12, pages 705-712.
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Sergey V. Ryabukhin, Andrey S. Plaskon, Eugeniy N. Ostapchuk, Dmitriy M. Volochnyuk, Oleg V. Shishkin, Alexander N. Shivanyuk & Andrey A. Tolmachev. (2007) A One-Step Fusion of 1,3-Thiazine and Pyrimidine Cycles. Organic Letters 9:21, pages 4215-4218.
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Ahmad R. Khosropour, Mohammad M. Khodaei & Mojtaba Beygzadeh. (2007) Highly convenient one‐pot conversion of aryl acylals or aryl aldehyde bisulfites into dihydropyrimidones using BI(NO 3 ) 3 ⋅5H 2 O . Heteroatom Chemistry 18:6, pages 684-687.
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V. Naveen Kumar, B. Sunil Kumar, P. Narsimha Reddy, Y. Thirupathi Reddy & B. Rajitha. (2007) SELECTFLUOR™ CATALYZED ONE POT SYNTHESIS OF DIHYDROPYRIMIDINONES: AN IMPROVED PROTOCOL FOR THE BIGINELLI REACTION. Heterocyclic Communications 13:1.
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Mostafa Mohammadpour Amini, Ahmad Shaabani & Ayoob Bazgir. (2006) Tangstophosphoric acid (H3PW12O40): An efficient and eco-friendly catalyst for the one-pot synthesis of dihydropyrimidin-2(1H)-ones. Catalysis Communications 7:11, pages 843-847.
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Rafael Martínez-Palou. (2006) Advances in Microwave-Assisted Combinatorial Chemistry Without Polymer-Supported Reagents. Molecular Diversity 10:3, pages 435-462.
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Hélio A. Stefani, Carlindo B. Oliveira, Roberta B. Almeida, Claudio M.P. Pereira, Rodolpho C. Braga, Rodrigo Cella, Vanessa C. Borges, Lucielli Savegnago & Cristina W. Nogueira. (2006) Dihydropyrimidin-(2H)-ones obtained by ultrasound irradiation: a new class of potential antioxidant agents. European Journal of Medicinal Chemistry 41:4, pages 513-518.
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Mark C. Bagley & M. Caterina Lubinu. 2006. Microwave-Assisted Synthesis of Heterocycles. Microwave-Assisted Synthesis of Heterocycles 31 58 .
V. Naveen Kumar, P. Someshwar, P. Narsimha Reddy, Y. Thirupathi Reddy & B. Rajitha. (2009) Copper dipyridine dichloride as a mild and efficient catalyst for a one pot condensation bigenelli reaction. Journal of Heterocyclic Chemistry 42:5, pages 1017-1019.
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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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Céline Simon, Thierry Constantieux & Jean Rodriguez. (2004) Utilisation of 1,3‐Dicarbonyl Derivatives in Multicomponent Reactions. European Journal of Organic Chemistry 2004:24, pages 4957-4980.
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Rina Ghosh, Swarupananda Maiti & Arijit Chakraborty. (2004) In(OTf)3-catalysed one-pot synthesis of 3,4-dihydropyrimidin-2(lH)-ones. Journal of Molecular Catalysis A: Chemical 217:1-2, pages 47-50.
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Ahmad Shaabani & Ayoob Bazgir. (2004) Microwave-assisted efficient synthesis of spiro-fused heterocycles under solvent-free conditions. Tetrahedron Letters 45:12, pages 2575-2577.
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C. Oliver Kappe & Alexander Stadler. 2004. Organic Reactions. Organic Reactions 1 116 .
Ji-Tai Li, Jun-Fen Han, Jin-Hui Yang & Tong-Shuang Li. (2003) An efficient synthesis of 3,4-dihydropyrimidin-2-ones catalyzed by NH2SO3H under ultrasound irradiation. Ultrasonics Sonochemistry 10:3, pages 119-122.
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C.Oliver Kappe & Alexander Stadler. 2003. Combinatorial Chemistry, Part B. Combinatorial Chemistry, Part B 197 223 .
Min Xia & Yan-Guang Wang. (2002) Soluble polymer-supported synthesis of Biginelli compounds. Tetrahedron Letters 43:43, pages 7703-7705.
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Jun Lu, Yin‐Juan Bai, Yan‐Hong Guo, Zhen‐Jun Wang & Huai‐Rang Ma. (2010) CoCl 2 ·6H 2 O or LaCl 3 ·7H 2 O Catalyzed Biginelli Reaction. One‐Pot Synthesis of 3,4‐Dihydropyrimidin‐2(1 H )‐ones . Chinese Journal of Chemistry 20:7, pages 681-687.
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Song Xue, Yan‐Cai Shen, Ya‐Li Li, Xiao‐Ming Shen & Qing‐Xiang Guo. (2010) Synthesis of 4‐Aryl‐3,4‐dihydropyrimidinones Using Microwave‐assisted Solventless Biginelli Reaction. Chinese Journal of Chemistry 20:4, pages 385-389.
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Mazaahir Kidwai, Shilpi Saxena, Richa Mohan & R. Venkataramanan. (2002) A novel one pot synthesis of nitrogen containing heterocycles: an alternate methodology to the Biginelli and Hantzsch reactions. J. Chem. Soc., Perkin Trans. 1:16, pages 1845-1846.
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Alexander Stadler & C. Oliver Kappe. (2001) Automated Library Generation Using Sequential Microwave-Assisted Chemistry. Application toward the Biginelli Multicomponent Condensation. Journal of Combinatorial Chemistry 3:6, pages 624-630.
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Helio A. Stefani & Paula M. Gatti. (2010) ChemInform Abstract: 3,4‐Dihydropyrimidin‐2(1H)‐ones: Fast Synthesis under Microwave Irradiation in Solvent Free Conditions.. ChemInform 31:40.
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