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Pure Appl. Chem., 2008, Vol. 80, No. 3, pp. 609-620

http://dx.doi.org/10.1351/pac200880030609

Diversity-oriented syntheses of functional π-systems by multicomponent and domino reactions

Thomas J. J. Müller1 and Daniel M. D'Souza2

1 Institute for Organic Chemistry and Macromolecular Chemistry, Heinrich Heine University Düsseldorf, Universitätsstrasse 1, D-40225 Düsseldorf, Germany
2 School of Chemistry, The University of Edinburgh, The King's Buildings, West Mains Road, Edinburgh EH9 3JJ, UK

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  • Kumar Maji Pradip, Ul Islam Rafique, Kumar Bera Sujit: RECENT PROGRESS IN METAL ASSISTED MULTICOMPONENT SYNTHESES OF HETEROCYCLES. HETEROCYCLES 2014, 89, 869. <http://dx.doi.org/10.3987/REV-13-781>
  • Volla Chandra M. R., Bäckvall Jan-E.: Palladium-Catalyzed Aerobic Domino Oxidative Carbocyclization-Alkynylation of Allenynes. Angew. Chem. 2013, 125, 14459. <http://dx.doi.org/10.1002/ange.201308448>
  • Volla Chandra M. R., Bäckvall Jan-E.: Palladium-Catalyzed Aerobic Domino Oxidative Carbocyclization-Alkynylation of Allenynes. Angew. Chem. Int. Ed. 2013, 52, 14209. <http://dx.doi.org/10.1002/anie.201308448>
  • Muschelknautz C., Mayer B., Rominger F., Müller T. J. J.: Consecutive three-component synthesis of film luminescent indolone merocyanines with L-amino acid ester donors. Chem Heterocycl Comp 2013, 49, 860. <http://dx.doi.org/10.1007/s10593-013-1320-3>
  • Rossi Renzo, Bellina Fabio, Lessi Marco, Manzini Chiara: Development and applications of highly selective palladium-catalyzed monocoupling reactions of (cyclo)alkenes and 1,3-alkadienes bearing two or three electrophilic sites and bis(enol triflates) with terminal alkynes. Tetrahedron 2013, 69, 7869. <http://dx.doi.org/10.1016/j.tet.2013.06.002>
  • Zhang Yongqiang, Wang Shengzheng, Wu Shanchao, Zhu Shiping, Dong Guoqiang, Miao Zhenyuan, Yao Jianzhong, Zhang Wannian, Sheng Chunquan, Wang Wei: Facile Construction of Structurally Diverse Thiazolidinedione-Derived Compounds via Divergent Stereoselective Cascade Organocatalysis and Their Biological Exploratory Studies. ACS Comb. Sci. 2013, 15, 298. <http://dx.doi.org/10.1021/co400022r>
  • Cinar Rahime, Nordmann Jan, Dirksen Elena, Müller Thomas J. J.: Domino synthesis of protochromic “ON–OFF–ON” luminescent 2-styryl quinolines. Org. Biomol. Chem. 2013, 11, 2597. <http://dx.doi.org/10.1039/c3ob27270b>
  • Teiber Marco, Giebeler Sönke, Lessing Timo, Müller Thomas J. J.: Efficient pseudo-five-component coupling-Fiesselmann synthesis of luminescent oligothiophenes and their modification. Org. Biomol. Chem. 2013, 11, 3541. <http://dx.doi.org/10.1039/c3ob40124c>
  • 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>
  • Ookubo Yuuya, Wakamiya Atsushi, Yorimitsu Hideki, Osuka Atsuhiro: Synthesis of a Library of Fluorescent 2-Aryl-3-trifluoromethylnaphthofurans from Naphthols by Using a Sequential Pummerer-Annulation/Cross-Coupling Strategy and their Photophysical Properties. Chem. Eur. J. 2012, 18, 12690. <http://dx.doi.org/10.1002/chem.201201261>
  • García-Melchor Max, Pacheco María C., Nájera Carmen, Lledós Agustí, Ujaque Gregori: Mechanistic Exploration of the Pd-Catalyzed Copper-Free Sonogashira Reaction. ACS Catal 2012, 2, 135. <http://dx.doi.org/10.1021/cs200526x>
  • Teiber Marco, Müller Thomas J. J.: Rapid consecutive three-component coupling-Fiesselmann synthesis of luminescent 2,4-disubstituted thiophenes and oligothiophenes. Chem Commn 2012, 48, 2080. <http://dx.doi.org/10.1039/c2cc17548g>
  • Demina M. M., Nguyen T. L. H., Shaglaeva N. S., Mareev A. V., Medvedeva A. S.: Highly efficient synthesis of 4-trialkylsilyl(germyl)-1H-1,2,3-triazole-5-carbaldehydes. Russ J Org Chem 2012, 48, 1582. <http://dx.doi.org/10.1134/S1070428012120196>
  • Sharma Sudhir K., Mandadapu Anil K., Kumar Brijesh, Kundu Bijoy: Synthesis of Iodo-Indoloazepinones in an Iodine-Mediated Three-Component Domino Reaction via a Regioselective 7-endo-dig Iodo-Cyclization Pathway±CDRI Communication No. 8094. J Org Chern 2011, 76, 6798. <http://dx.doi.org/10.1021/jo201228t>
  • Willy Benjamin, Müller Thomas J. J.: Rapid One-Pot, Four-Step Synthesis of Highly Fluorescent 1,3,4,5-Tetrasubstituted Pyrazoles§. Org Lett 2011, 13, 2082. <http://dx.doi.org/10.1021/ol2004947>
  • Muschelknautz Christian, Frank Walter, Müller Thomas J. J.: Rapid Access to Unusual Solid-State Luminescent Merocyanines by a Novel One-Pot Three-Component Synthesis∥. Org Lett 2011, 13, 2556. <http://dx.doi.org/10.1021/ol200655s>
  • Chen Xiaopeng, Wang Hongbo, Jin Xiaohan, Feng Jinwu, Wang Yanguang, Lu Ping: Palladium catalyzed bicyclization of 1,8-diiodonaphthalene and tertiary propargylic alcohols to phenalenones and their applications as fluorescent chemosensor for fluoride ions. Chem Commun 2011, 47, 2628. <http://dx.doi.org/10.1039/c0cc04875e>
  • Schönhaber Jan, Müller Thomas J. J.: Luminescent bichromophoric spiroindolones – synthesis and electronic properties. Biomol Chem 2011, 9, 6196. <http://dx.doi.org/10.1039/c1ob05703k>
  • Grotkopp Oliver, Ahmad Atia, Frank Walter, Müller Thomas J. J.: Blue-luminescent 5-(3-indolyl)oxazoles via microwave-assisted three-component coupling–cycloisomerization–Fischer indole synthesis. Biomol Chem 2011, 9, 8130. <http://dx.doi.org/10.1039/c1ob06153d>
  • Willy Benjamin, Müller Thomas J. J.: Three-component synthesis of benzo[b][1,5]thiazepines via coupling–addition–cyclocondensation sequence. Mol Divers 2010, 14, 443. <http://dx.doi.org/10.1007/s11030-009-9223-z>
  • Chamas Zein el abidine, Dietz Olivier, Aubert Emmanuel, Fort Yves, Mamane Victor: Synthesis of new pentacyclic chromophores through a highly regio- and diastereoselective cascade process. Org Biomol Chem 2010, 8, 4815. <http://dx.doi.org/10.1039/c0ob00390e>
  • Merkul Eugen, Oeser Thomas, Müller Thomas J. J.: Consecutive Three-Component Synthesis of Ynones by Decarbonylative Sonogashira Coupling. Chem Eur J 2009, 15, 5006. <http://dx.doi.org/10.1002/chem.200900119>
  • Zhou Wang, Zhang Liangren, Jiao Ning: The tandem reaction combining radical and ionic processes: an efficient approach to substituted 3,4-dihydroquinolin-2-ones. Tetrahedron 2009, 65, 1982. <http://dx.doi.org/10.1016/j.tet.2009.01.027>
  • Carpita Adriano, Ribecai Arianna: Convenient copper- and solvent-free Sonogashira-type alkynylation of aryl iodides and bromides using Pd EnCat™. Tetrahetron Lett 2009, 50, 204. <http://dx.doi.org/10.1016/j.tetlet.2008.10.130>
  • Mueller Thomas J. J., D'Souza Daniel M.: ChemInform Abstract: Diversity-Oriented Syntheses of Functional π-Systems by Multicomponent and Domino Reactions. ChemInform 2008, 39. <http://dx.doi.org/10.1002/chin.200832249>
  • Willy Benjamin, Müller Thomas J. J.: Regioselective Three-Component Synthesis of Highly Fluorescent 1,3,5-Trisubstituted Pyrazoles. Eur J Org Chem 2008, 2008, 4157. <http://dx.doi.org/10.1002/ejoc.200800444>
  • Willy Benjamin, Dallos Timea, Rominger Frank, Schönhaber Jan, Müller Thomas J. J.: Three-Component Synthesis of Cryofluorescent 2,4-Disubstituted 3H-1,5-Benzodiazepines - Conformational Control of ­Emission Properties. Eur J Org Chem 2008, 2008, 4796. <http://dx.doi.org/10.1002/ejoc.200800619>
  • D'Souza Daniel M, Müller Thomas J J: Catalytic alkynone generation by Sonogashira reaction and its application in three-component pyrimidine synthesis. UNKNOWN 2008, 3, 1660. <http://dx.doi.org/10.1038/nprot.2008.152>