Pure Appl. Chem., 2008, Vol. 80, No. 3, pp. 609-620
doi:10.1351/pac200880030609
Diversity-oriented syntheses of functional π-systems by multicomponent and domino reactions*
Thomas J. J. Müller1, and Daniel M. D'Souza2
1Institute for Organic Chemistry and Macromolecular Chemistry, Heinrich Heine University Düsseldorf, Universitätsstrasse 1, D-40225 Düsseldorf, Germany; 2School of Chemistry, The University of Edinburgh, The King's Buildings, West Mains Road, Edinburgh EH9 3JJ, UK
Abstract:
Functional π-electron systems can be synthesized in a diversity-oriented fashion by applying multicomponent and domino reactions. Based upon alkyne activation by Sonogashira coupling, reactive triple or double bonds become the key functionality for sequential and consecutive synthesis of heterocycles, such as β-amino vinyl nitrothiophenes, δ-amino propenylidene indolones, indolizines, furans, pyrroles, annelated 2-amino pyridines, and spirocyclic benzofuranones and indolones. All these chromophores and fluorophores possess peculiar properties such as nonlinear optical (NLO) activity, pH-sensitivity, distinct solid-state fluorescence, or large Stokes shifts.
Keywords: catalysis; CC-coupling; chromophores; domino reactions; multicomponent reactions.
*Paper based on a presentation at the 12th International Symposium on Novel Aromatic Compounds (ISNA-12), 22-27 July 2007, Awaji Island, Japan. Other presentations are published in this issue, pp. 411-667.
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