CrossRef enabled

PAC Archives

Archive →

Pure Appl. Chem., 2004, Vol. 76, No. 5, pp. 1017-1024

http://dx.doi.org/10.1351/pac200476051017

Solid- and solution-phase synthesis of bioactive dihydropyrimidines

D. Dallinger, A. Stadler and C. O. Kappe

Institute of Chemistry, Karl-Franzens-University Graz, Austria

CrossRef Cited-by theme picture

CrossRef Cited-by Linking

  • Quan Zheng-Jun, Lv Ying, Jing Fu-Qiang, Jia Xiao-Dong, Huo Cong-De, Wang Xi-Cun: Chemoselective Carbon-Carbon Cross-Coupling via Palladium-Catalyzed Copper-Mediated CS Cleavage of Disulfides. Adv. Synth. Catal. 2014, 356, 325. <http://dx.doi.org/10.1002/adsc.201300776>
  • Godhani Dinesh R., Dobariya Purvesh B., Jogel Anand A., Sanghani Anil M., Mehta Jignasu P.: An efficient synthesis, characterization, and antimicrobial screening of tetrahydropyrimidine derivatives. Med Chem Res 2014, 23, 2417. <http://dx.doi.org/10.1007/s00044-013-0840-9>
  • Alinezhad Heshmatollah, Tajbakhsh Mahmood, Norouzi Mohammad, Baghery Saeed, Akbari Maryam: Protic pyridinium ionic liquid: As an efficient, green and environmentally friendly catalyst for the one-pot synthesis of amidoalkyl naphthol derivatives. Comptes Rendus Chimie 2014, 17, 7. <http://dx.doi.org/10.1016/j.crci.2012.10.012>
  • Safari Javad, Gandomi-Ravandi Soheila: Fe3O4–CNTs nanocomposites: a novel and excellent catalyst in the synthesis of diarylpyrimidinones using grindstone chemistry. RSC Adv. 2014, 4, 11486. <http://dx.doi.org/10.1039/c3ra47827k>
  • Quan Zheng-Jun, Hu Wang-Hua, Zhang Zhang, Da Yu-Xia, Jia Xiao-Dong, Wang Xi-Cun: One-Pot Synthesis of Allylamine Derivatives by Iodine- Catalyzed Three-Component Reaction of N-Heterocycles, Paraformaldehyde and Styrenes. Adv. Synth. Catal. 2013, 355, 891. <http://dx.doi.org/10.1002/adsc.201201097>
  • Quan Zhengjun, Jing Fuqiang, Zhang Zhang, Da Yuxia, Wang Xicun: Cross-Coupling Reactions of Pyrimidin-2-yl Sulfonates with Phenols and Anilines: An Efficient Approach to C2-Functionalized Pyrimidines. Chin. J. Chem. 2013, 31, 1495. <http://dx.doi.org/10.1002/cjoc.201300536>
  • Singh Kamaljit, Chopra Rakesh: Highly Regioselective Addition of Organozinc Reagents to 2-Oxo-1,2-dihydropyrimidine-5-carboxylates Activated by BF3 ·OEt2 : Synthesis of 2-Oxo-1,2,3,4-tetrahydropyrimidine-5-carboxylates. Eur. J. Org. Chem. 2013, 2013, 6124. <http://dx.doi.org/10.1002/ejoc.201300539>
  • Quan Zheng-Jun, Jing Fu-Qiang, Zhang Zhang, Da Yu-Xia, Wang Xi-Cun: Palladium(II) Catalyzed Suzuki/Sonogashira Cross-Coupling Reactions of Sulfonates: An Efficient Approach to C2-Functionalized Pyrimidines and Pyridines. Eur. J. Org. Chem. 2013, 2013, 7175. <http://dx.doi.org/10.1002/ejoc.201300592>
  • Bamoniri A., Mirjalili B. F., Nazemian S.: Nano silica phosphoric acid: an efficient catalyst for the one-pot synthesis of amidoalkyl naphthols under solvent-free condition. J IRAN CHEM SOC 2013. <http://dx.doi.org/10.1007/s13738-013-0336-z>
  • Quan Zheng-Jun, Lv Ying, Wang Zhong-Jie, Zhang Zhang, Da Yu-Xia, Wang Xi-Cun: Molecular iodine-mediated S–N and C–N cross-coupling and oxidative aromatization of 3,4-dihydropyrimidin-2(1H)-thiones with secondary amines. Tetrahedron Letters 2013, 54, 1884. <http://dx.doi.org/10.1016/j.tetlet.2013.01.113>
  • Guirado Antonio, Alarcón Enrique, Vicente Yesica, Andreu Raquel: A new improved method for the synthesis of 2,4-diarylpyrimidines starting from 2,2,2-trichloroethylideneacetophenones. Tetrahedron Letters 2013, 54, 5115. <http://dx.doi.org/10.1016/j.tetlet.2013.07.075>
  • Quan Zheng-Jun, Hu Wang-Hua, Jia Xiao-Dong, Zhang Zhang, Da Yu-Xia, Wang Xi-Cun: A Domino Desulfitative Coupling/Acylation/Hydration Process Cocatalyzed by Copper(I) and Palladium(II): Synthesis of Highly Substituted and Functionalized Pyrimidines. Adv. Synth. Catal. 2012, 354, 2939. <http://dx.doi.org/10.1002/adsc.201200402>
  • Prosa Nicolò, Turgis Raphaël, Piccardi Riccardo, Scherrmann Marie-Christine: Soluble Polymer-Supported Flow Synthesis: A Green Process for the Preparation of Heterocycles. Eur J Org 2012, 2012, 2188. <http://dx.doi.org/10.1002/ejoc.201101726>
  • Mistry Sunil R., Maheria Kalpana C.: Synthesis of diarylpyrimidinones (DAPMs) using large pore zeolites. Journal of Molecular Catalysis A 2012, 355, 210. <http://dx.doi.org/10.1016/j.molcata.2011.12.019>
  • Garibov Emin N., Gojayeva Sevinj S., Allahverdiyev Mirze A., Gurbanov Atash V. Gurbanov, Brito Iván: 1-(6-Methyl-3-phenyl-2-sulfanylidene-1,2,3,4-tetrahydropyrimidin-5-yl)ethanone. Acta Crystallogr Sect E Struct Rep 2012, 68, o276. <http://dx.doi.org/10.1107/S1600536811055309>
  • Tron Gian Cesare, Minassi Alberto, Appendino Giovanni: Pietro Biginelli: The Man Behind the Reaction. Eur J Org Chem 2011, 2011, 5541. <http://dx.doi.org/10.1002/ejoc.201100661>
  • Singh Jagjeet, Mahajan Nitu, Sharma Rattan L., Razdan Tej K.: Synthesis of tetrahydropyrimidino[4,3-a]isoquinolines via regiospecific N-alkylation-annulation of 4-aryldihydropyrimidinones. J  Heterocycl Chem 2011, 48, 1398. <http://dx.doi.org/10.1002/jhet.768>
  • MISTRY SUNIL R, JOSHI RIKESH S, MAHERIA KALPANA C: Zeolite H-BEA catalysed multicomponent reaction: One-pot synthesis of amidoalkyl naphthols – Biologically active drug-like molecules. J Chem Sci 2011, 123, 427. <http://dx.doi.org/10.1007/s12039-011-0095-2>
  • Da Yu Xia, Zhang Zhang, Quan Zheng Jun: Intermolecular cyclocondensation reaction of 3,4-dihydropyrimidine-2-thione under the Mitsunobu reaction conditions. Chin Chem Lett 2011, 22, 679. <http://dx.doi.org/10.1016/j.cclet.2010.12.041>
  • Quan Zheng-Jun, Ren Rong-Guo, Jia Xiao-Dong, Da Yu-Xia, Zhang Zhang, Wang Xi-Cun: N-Alkoxymethylation of heterocyclic compounds with diethyl phosphite via cleavage of P–O bond. Tetrahedron 2011, 67, 2462. <http://dx.doi.org/10.1016/j.tet.2011.01.061>
  • Wang Xi-Cun, Yang Guo-Jun, Jia Xiao-Dong, Zhang Zhang, Da Yu-Xia, Quan Zheng-Jun: Synthesis of C2-functionalized pyrimidines from 3,4-dihydropyrimidin-2(1H)-ones by the Mitsunobu coupling reaction. Tetrahedron 2011, 67, 3267. <http://dx.doi.org/10.1016/j.tet.2011.02.046>
  • Kushnir O. V., Mel’nichenko N. V., Vovk M. V.: Heterocyclizations of functionalized heterocumulenes with C,N-, C,O-, and C,S-binucleophiles: XIII. Synthesis of dialkyl 2-oxo-3-allyl-1,2,3,6-tetrahydropyrimidine-4,5-dicarboxylates and their reaction with arylhydroxymoyl chlorides. Russ J Org Chem 2011, 47, 1727. <http://dx.doi.org/10.1134/S1070428011110133>
  • Wang Xi-Cun, Wei Ying, Da Yu-Xia, Zhang Zhang, Quan Zheng-Jun: One-Step Synthesis of Tetrazolo[1,5-a]pyrimidines by Cyclization Reaction of Dihydropyrimidine-2-thiones with Sodium Azide. HETEROCYCLES 2011, 83, 2811. <http://dx.doi.org/10.3987/COM-11-12351>
  • Prashantha Kumar B. R., Masih Pankaj, Karthikeyan E., Bansal Ankur, Suja, Vijayan Pottekad: Synthesis of novel Hantzsch dihydropyridines and Biginelli dihydropyrimidines of biological interest: a 3D-QSAR study on their cytotoxicity. Med Chem Res 2010, 19, 344. <http://dx.doi.org/10.1007/s00044-009-9195-7>
  • Magerramov A. M., Kurbanov A. V., Khrustalev V. N., Godzhaeva S. S., Garibov É. N., Farzaliev V. M., Allakhverdiev M. A.: Crystal structure of ethyl 9-methyl-10-phenyl-11-thioxo-8-oxa-10,12-diazatricyclo[7.3.1.02.7] trideca-2(7),3,5-trien-13-carboxylate. J Struct Chem 2010, 51, 968. <http://dx.doi.org/10.1007/s10947-010-0148-2>
  • Quan Zheng-Jun, Wang Xi-Cun, Ren Rong-Guo, Da Yu-Xia, Zhang Zhang, Jia Xiao-Dong, Yang Cai-Xia: One-Pot Two-Step Synthesis of N3-Functionalized 3,4-Dihydropyrimidinones in the Presence of TMSCl. HETEROCYCLES 2010, 81, 1827. <http://dx.doi.org/10.3987/COM-10-11968>
  • De Souza Rodrigo O. M. A., da Penha Eduardo T. , Milagre Humberto M. S., Garden Simon J., Esteves Pierre M., Eberlin Marcos N., Antunes Octavio A. C.: The Three-Component Biginelli Reaction: A Combined Experimental and Theoretical Mechanistic Investigation. Chem Eur J 2009, 15, 9799. <http://dx.doi.org/10.1002/chem.200900470>
  • Nagarapu Lingaiah, Bantu Rajashaker, Mereyala Hari Babu: TMSCl-mediated one-pot, three-component synthesis of 2H-indazolo[2,1-b]phthalazine-triones. J Heterocyclic Chem 2009, 46, 728. <http://dx.doi.org/10.1002/jhet.135>
  • Kolosov Maksim A., Orlov Valeriy D., Beloborodov Dmitriy A., Dotsenko Victor V.: A chemical placebo: NaCl as an effective, cheapest, non-acidic and greener catalyst for Biginelli-type 3,4-dihydropyrimidin-2(1H)-ones (-thiones) synthesis. Mol Divers 2009, 13, 5. <http://dx.doi.org/10.1007/s11030-008-9094-8>
  • Lebed’ P. S., Kos P. O., Polovinko V. V., Tolmachev A. A., Vovk M. V.: Synthesis of new polyfunctional 5,6,7,8-tetrahydroimidazo-[1,5-c]pyrimidin-5-ones by the aza-Wittig reaction followed by intramolecular cyclization and 1,3-prototropic shift. Russ J Org Chem 2009, 45, 921. <http://dx.doi.org/10.1134/S1070428009060207>
  • Yadav Lal Dhar S., Rai Ankita, Rai Vijai K., Awasthi Chhama: Chiral ionic liquid-catalyzed Biginelli reaction: stereoselective synthesis of polyfunctionalized perhydropyrimidines. Tetrahedron 2008, 64, 1420. <http://dx.doi.org/10.1016/j.tet.2007.11.044>
  • Chermahini Alireza Najafi, Dabbagh Hossein A., Teimouri Abbas, Kar Tapas, Scheiner Steve, Li Leijun, Ben Said Ridha, Tangour Bahoueddine, Barthelat Jean-Claude: Theoretical studies on tautomerism of dihydropyrimidine tautomers. Journal of Molecular Structure: THEOCHEM 2008, 857, 105. <http://dx.doi.org/10.1016/j.theochem.2008.02.012>
  • Virsodia Vijay R., Vekariya Nikhil R., Manvar Atul T., Khunt Rupesh C., Marvania Bhavin R., Savalia Bharat S., Shah Anamik K.: Catalyst-Free, Rapid Synthesis of Fused Bicyclic Thiazolo-Pyrimidine and Pyrimido-Thiazine Derivatives by a Microwave-Assisted Method. Phosphorus, Sulfur, and Silicon and the Related Elements 2008, 184, 34. <http://dx.doi.org/10.1080/10426500802077564>
  • Shanmugam P., Boobalan P., Perumal P.T.: A novel method for the synthesis of highly functionalized 3,4-dihydropyrimidin-2(1H)-ones through the 1,4-addition on pyrimidin-2(1H)-ones. Tetrahedron 2007, 63, 12215. <http://dx.doi.org/10.1016/j.tet.2007.09.066>
  • Yadav Lal Dhar S., Awasthi Chhama, Rai Vijai K., Rai Ankita: Biorenewable and mercaptoacetylating building blocks in the Biginelli reaction: synthesis of thiosugar-annulated dihydropyrimidines. Tetrahetron Lett 2007, 48, 4899. <http://dx.doi.org/10.1016/j.tetlet.2007.05.057>
  • Dallinger Doris, Stadler Alexander, Kappe C. Oliver: Solid- and Solution-Phase Synthesis of Bioactive Dihydropyrimidines. ChemInform 2004, 35. <http://dx.doi.org/10.1002/chin.200452250>