Microwave-assisted three-component coupling-addition-SNAr (CASNAR) sequences to annelated 4H-thiopyran-4-ones

Benjamin Willy; Walter Frank; Thomas J. J. Müller

doi:10.1039/B917627F

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Microwave-assisted three-component coupling-addition-S_NAr (CASNAR) sequences to annelated 4H-thiopyran-4-ones†

Benjamin Willy,^a Walter Frank ‡^b and Thomas J. J. Müller*^a

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* Corresponding authors

^a Institut für Organische Chemie und Makromolekulare Chemie, Heinrich-Heine-Universität Düsseldorf, Universitätsstr., Düsseldorf, Germany
E-mail: ThomasJJ.Mueller@uni-duesseldorf.de
Fax: +492118114324

^b Lehrstuhl für Anorganische Chemie und Strukturchemie der Heinrich-Heine-Universität Düsseldorf, Universitätsstraße, Düsseldorf, Germany

Abstract

A whole family of annelated 4H-thiopyran-4-ones as the core structural unit was readily synthesized in good yields by a microwave-assisted coupling-addition-S_NAr (CASNAR) sequence starting from readily available (het)aroyl chlorides, alkynes and sodium sulfide nonahydrate in a consecutive one-pot three-component reaction. All representatives display a pronounced halochromicity of the absorption bands upon protonation. According to DFT calculations, the electronic ground state of the annelated 4H-thiopyran-4-ones possess a considerable zwitterionic character.

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Article information

DOI: https://doi.org/10.1039/B917627F
Article type: Paper
Submitted: 26 Aug 2009
Accepted: 28 Sep 2009
First published: 23 Oct 2009

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Org. Biomol. Chem., 2010,8, 90-95

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Microwave-assisted three-component coupling-addition-S_NAr (CASNAR) sequences to annelated 4H-thiopyran-4-ones

B. Willy, W. Frank and T. J. J. Müller, Org. Biomol. Chem., 2010, 8, 90 DOI: 10.1039/B917627F

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Organic & Biomolecular Chemistry