Blue-luminescent 5-(3-indolyl)oxazoles via microwave-assisted three-component coupling–cycloisomerization–Fischer indole synthesis†‡,10.1039/C1OB06153D

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

Oliver Grotkopp,Atia Ahmad,Walter Frank,Thomas J. J. Müller

Organic & Biomolecular Chemistry Pub Date : 09/09/2011 00:00:00 , DOI:10.1039/C1OB06153D

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.