Issue 23, 2011
From the journal:

Organic & Biomolecular Chemistry

Blue-luminescent 5-(3-indolyl)oxazoles via microwave-assisted three-component coupling–cycloisomerization–Fischer indole synthesis†‡

Oliver Grotkopp,a   Atia Ahmad,a   Walter Frankb  and  Thomas J. J. Müller*a  

* Corresponding authors

a Lehrstuhl für Organische Chemie, Institut für Organische Chemie und Makromolekulare Chemie, Heinrich-Heine-Universität Düsseldorf, Universitätsstraße 1, Düsseldorf, Germany
E-mail: ThomasJJ.Mueller@uni-duesseldorf.de
Fax: +49 (0)211 8114324
Tel: +49 (0)211 8112298

b Institut für Anorganische Chemie und Strukturchemie, Heinrich-Heine-Universität Düsseldorf, Universitätsstraße 1, Düsseldorf, Germany

Abstract

Aryl-substituted 5-(3-indolyl)oxazoles are readily synthesized in a novel one-pot three-component synthesis consisting of a microwave assisted sequence of Sonogashira coupling, an acid-catalyzed cycloisomerization, and a concluding Fischer indole synthesis. All title compounds are intensely blue-luminescent with large Stokes shifts upon UV-irradiation. The experimental absorption spectra are rationalized by ZINDO-CI computations based upon DFT geometry optimization.

Graphical abstract: Blue-luminescent 5-(3-indolyl)oxazoles via microwave-assisted three-component coupling–cycloisomerization–Fischer indole synthesis

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Article information

DOI
https://doi.org/10.1039/C1OB06153D
Article type
Paper
Submitted
12 Jul 2011
Accepted
08 Sep 2011
First published
09 Sep 2011

Org. Biomol. Chem., 2011,9, 8130-8140

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Blue-luminescent 5-(3-indolyl)oxazoles via microwave-assisted three-component coupling–cycloisomerization–Fischer indole synthesis

O. Grotkopp, A. Ahmad, W. Frank and T. J. J. Müller, Org. Biomol. Chem., 2011, 9, 8130 DOI: 10.1039/C1OB06153D

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