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Synthesis 2008(2): 293-303  
DOI: 10.1055/s-2007-1000856
PAPER
© Georg Thieme Verlag Stuttgart · New York

Novel Microwave-Assisted One-Pot Synthesis of Isoxazoles by a Three-Component Coupling-Cycloaddition Sequence

Benjamin Willya, Frank Romingerb, Thomas J. J. Müller*a
a Institut für Organische Chemie und Makromolekulare Chemie, Lehrstuhl für Organische Chemie, Heinrich-Heine-Universität Düsseldorf, Universitätsstraße 1, 40225 Düsseldorf, Germany
Fax: +49(211)8114324; e-Mail: ThomasJJ.Mueller@uni-duesseldorf.de;
b Organisch-Chemisches Institut, Ruprecht-Karls-Universität Heidelberg, Im Neuenheimer Feld 270, 69210 Heidelberg, Germany
Further Information

Publication History

Received 28 August 2007
Publication Date:
18 December 2007 (online)

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Abstract

The consecutive Sonogashira coupling of acid chlorides with terminal alkynes, followed by 1,3-dipolar cycloaddition under dielectric heating of in situ generated nitrile oxides from hydroximinoyl chlorides furnishes isoxazoles in moderate to good yields in the sense of a one-pot three-component reaction.

Key words

alkynes - cross-couplings - cycloaddition - isoxazole - microwave reaction

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Crystallographic data (excluding structure factors) for the structures reported in this paper have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication nos. CCDC-661680 (5w), and CCDC-661681 (6a). Copies of the data can be obtained free of charge on application to CCDC, 12 Union Road, Cambridge CB2 1EZ, UK [Fax: +44(1223)336033; E-mail: deposit@ccdc.cam.ac.uk].