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

Benjamin Willy, Frank Rominger, Thomas J. J. Müller*

*Institut für Organische Chemie und Makromolekulare Chemie, Lehrstuhl für Organische Chemie, Heinrich-Heine-Universität Düsseldorf, Universitätsstraße 1, 40225 Düsseldorf, Germany, Email: ThomasJJ.Muelleruni-duesseldorf.de

B. Willy, F. Rominger, T. J. J. Müller, Synthesis, 2008, 293-303.

DOI: 10.1055/s-2007-1000856


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.

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2-Oxazol-5-ylethanones by Consecutive Three-Component Amidation-Coupling-Cycloisomerization (ACCI) Sequence

E. Merkul, O. Grotkopp, T. J. J. Müller, Synthesis, 2009, 502-507.


Key Words

alkynes, cross-couplings, cycloaddition, isoxazoles, microwave synthesis


ID: J66-Y2008-0230