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

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

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.