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Pure Appl. Chem., 2010, Vol. 82, No. 9, pp. 1749-1759

http://dx.doi.org/10.1351/PAC-CON-09-09-39

Published online 2010-06-04

Use of functionalized β-lactams as building blocks in heterocyclic chemistry

Matthias D’hooghe, Stijn Dekeukeleire, Erika Leemans and Norbert De Kimpe

Department of Organic Chemistry, Faculty of Bioscience Engineering, Ghent University, Coupure links 653, B-9000 Ghent, Belgium

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  • Raj Raghu, Sharma Vaishali, Hopper Melissa J., Patel Neal, Hall Dominique, Wrischnik Lisa A., Land Kirkwood M., Kumar Vipan: Synthesis and preliminary in vitro activity of mono- and bis-1H-1,2,3-triazole-tethered β-lactam–isatin conjugates against the human protozoal pathogen Trichomonas vaginalis. Med Chem Res 2014. <http://dx.doi.org/10.1007/s00044-014-0956-6>
  • Rajesh R., Suresh M., Raghunathan R.: A tactical approach for the synthesis of novel β-lactam-substituted, polycyclic-fused isoxazolidine derivatives via an intramolecular [3+2] cycloaddition reaction. Tetrahedron Letters 2014, 55, 699. <http://dx.doi.org/10.1016/j.tetlet.2013.11.117>
  • Mollet Karen, Goossens Hannelore, Piens Nicola, Catak Saron, Waroquier Michel, Törnroos Karl W., Van Speybroeck Veronique, D'hooghe Matthias, De Kimpe Norbert: Synthesis of 2-Hydroxy-1,4-oxazin-3-ones through Ring Transformation of 3-Hydroxy-4-(1,2-dihydroxyethyl)-β-lactams and a Study of Their Reactivity. Chem. Eur. J. 2013, 19, 3383. <http://dx.doi.org/10.1002/chem.201203314>
  • Vandekerckhove Stéphanie, D’hooghe Matthias: Exploration of aziridine- and β-lactam-based hybrids as both bioactive substances and synthetic intermediates in medicinal chemistry. Bioorganic & Medicinal Chemistry 2013, 21, 3643. <http://dx.doi.org/10.1016/j.bmc.2013.04.033>
  • Fodor Lajos, Csomós Péter, Fülöp Ferenc, Csámpai Antal, Sohár Pál: Preparation and ring transformation of isomeric β-lactam derivatives of bicyclic 1,3-thiazines. Tetrahedron 2013, 69, 410. <http://dx.doi.org/10.1016/j.tet.2012.09.102>
  • Dekeukeleire Stijn, Dhooghe Matthias, Vanwalleghem Matthieu, Van Brabandt Willem, De Kimpe Norbert: Asymmetric synthesis of 4-formyl-1-(?-haloalkyl)-?-lactams and their transformation to functionalized piperazines and 1,4-diazepanes. Tetrahedron 2012, 68, 10827. <http://dx.doi.org/10.1016/j.tet.2011.09.136>
  • Mollet Karen, Dhooghe Matthias, De Kimpe Norbert: Stereoselective synthesis of bicyclic tetrahydrofuran-fused ?-lactams and their conversion into methyl cis-3-aminotetrahydrofuran-2-carboxylates. Tetrahedron 2012, 68, 10787. <http://dx.doi.org/10.1016/j.tet.2012.01.001>
  • Fodor Lajos, Csomós Péter, Csámpai Antal, Sohár Pál: Ring transformations of β-lactam-condensed 1,3-benzothiazines to isoquinoline and thiazole derivatives by sulfur extrusion and addition sequences. Tetrahedron 2012. <http://dx.doi.org/10.1016/j.tet.2012.05.033>
  • D’hooghe Matthias, Mollet Karen, De Vreese Rob, Jonckers Tim H. M., Dams Géry, De Kimpe Norbert: Design, Synthesis, and Antiviral Evaluation of Purine-β-lactam and Purine-aminopropanol Hybrids. J. Med. Chem. 2012, 55, 5637. <http://dx.doi.org/10.1021/jm300383k>
  • Kwon Soon Ho, Lee Sang Min, Byun Sang Moon, Chin Jik, Kim B. Moon: Short Synthesis of Enantiopure trans-3-Arylpiperazine-2-carboxylic Acid Derivatives via Diaza-Cope Rearrangement. Org. Lett. 2012, 14, 3664. <http://dx.doi.org/10.1021/ol301506b>
  • D’hooghe Matthias, De Kimpe Norbert, Mollet Karen, Broeckx Leen: Synthesis of Stereodefined 3,4-Disubstituted Piperidines through Rearrangement of 2-(2-Bromo-1,1-dimethylethyl)azetidines. Heterocycle 2012, 84, 431. <http://dx.doi.org/10.3987/COM-11-S(P)3>
  • D'Hooghe Matthias, Dekeukeleire Stijn, Leemans Erika, De Kimpe Norbert: ChemInform Abstract: Use of Functionalized β-Lactams as Building Blocks in Heterocyclic Chemistry. ChemInform 2011, 42, no. <http://dx.doi.org/10.1002/chin.201109269>
  • Singh Pardeep, Sachdeva Shaveta, Raj Raghu, Kumar Vipan, Mahajan Mohinder P., Nasser Shereen, Vivas Livia, Gut Jiri, Rosenthal Phillip J., Feng Tzu-Shean: Antiplasmodial and cytotoxicity evaluation of 3-functionalized 2-azetidinone derivatives. Biorg Med Chem Lett 2011, 21, 4561. <http://dx.doi.org/10.1016/j.bmcl.2011.05.119>
  • Mollet Karen, Catak Saron, Waroquier Michel, Van Speybroeck Veronique, D’hooghe Matthias, De Kimpe Norbert: Stereoselective Synthesis of cis-3,4-Disubstituted Piperidines through Ring Transformation of 2-(2-Mesyloxyethyl)azetidines. J Org Chern 2011, 76, 8364. <http://dx.doi.org/10.1021/jo201556t>